Seiji MORIProfessor
■Researcher basic information
Organization
Research Areas
- Nanotechnology/Materials, Biochemistry, computational biochemistry
- Nanotechnology/Materials, Inorganic and coordination chemistry, theoretical inorganic chemistry
- Nanotechnology/Materials, Structural/physical organic chemistry, Theoretical Organic Chemistry
- Nanotechnology/Materials, Basic physical chemistry, Computational/theoretical chemistry
- Life sciences, Bioorganic chemistry, Theoretical Organic Chemistry
Research Keyword
Educational Background
Career
- Apr. 2012 - Present, Ibaraki University, College of Science, Professor
- Apr. 2022 - Mar. 2025, Graduate School of Science and Engineering, Institute of Quantum Beam Science, Director
- Apr. 2021 - Mar. 2022, 茨城大学理学部理学科長・大学院理工学研究科（理学野）化学領域長
- Apr. 2018 - Mar. 2021, Graduate School of Science and Engineering, Ibaraki University, Institute of Quantum Beam Science, Deputy Director
- Apr. 2015 - Mar. 2017, Ibaraki University, Assistant Vice President
- Apr. 2014 - Mar. 2015, Ibaraki University, College of Science, Chairperson of Chemistry Domain
- Apr. 2007 - Mar. 2012, Ibaraki University, College of Science, Associate professor
- Apr. 2005 - Mar. 2007, Ibaraki University, College of Science, Associate Professor
- Jun. 2006 - Jul. 2006, Emory University, Atlanta, GA, USA, Cherry L. Emerson center visiting fellow
- Jul. 2005 - Sep. 2005, Mindanao Institute of Technology-Iligan Institute of Technology, 理学部, Visiting professor
- Sep. 2005, JSPS-DAAD exchange fellow
- Apr. 2001 - Mar. 2005, Ibaraki University, Department of Environmental Science, College of Science, Associate Professor
- Oct. 2000 - Mar. 2001, Ibaraki University, Department of Environmental Science, College of Science, Assistant Professor
- 1998 - 2000, JSPS, Postdoctoral fellow
- 1998 - 2000, Emory University, USA, Postdoctoral fellow,
- 1996 - 1998, JSPS, Predoctoral fellow
Member History
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(Message from Researchers)
(研究経歴),Theoretical studies on the reaction mechanisms on biosyntheses of biological active compounds and organic/inorganic/organometallic reactions.
■Research activity information
Award
Paper
- NHC-Mediated Radical Acylation Catalyzed by Thiamine- and Flavin-Dependent Enzymes.
Shunsuke Kato; Shuto Fujisawa; Yuto Adachi; Mitsuhiro Bandai; Yutaro Mori; Seiji Mori; Tomokazu Shirai; Takashi Hayashi, Cross-coupling reactions between short-lifetime radicals are challenging reactions in organic chemistry. Here, we report the development of an N-heterocyclic carbene (NHC)-mediated radical coupling reaction based on the catalytic machinery of thiamine- and flavin-dependent enzymes. Through a series of enzyme screenings, we found that acetolactate synthase from Thermobispora bispora (TbALS) and its engineered variants exhibit promising catalytic activity toward abiotic radical acylation reactions of α-bromo carbonyl compounds. Notably, the TbALS variant has higher catalytic activity for small nonaromatic substrates despite forming less stable radical intermediates. Furthermore, the catalytic system of TbALS can be applied to photocatalytic reactions utilizing the photoredox properties of FAD. Nonbenzylic alkyl radicals generated from N-acyloxyphthalimides are efficiently converted into the corresponding dialkyl ketones under irradiation of a blue LED. These findings highlight the utility of thiamine- and flavin-dependent enzymes for achieving selective cross-coupling reactions of short-lifetime radicals.
Journal of the American Chemical Society, 15 Apr. 2025 - Highly Enantioselective Organocatalytic Mannich Reaction of α-Benzylidene Succinimides with N-Boc Imines: Experimental and Theoretical Studies.
Kodai Kimura; Yuto Shimizu; Katsuya Kanno; Itaru Sato; Seiji Mori; Takeshi Oriyama, Corresponding, The development of efficient and practical methods for the construction of chiral succinimide frameworks, which are the backbone of various natural products and widely studied in the field of pharmaceuticals, attracts considerable research attention. In this study, an asymmetric Mannich reaction of α-benzylidene succinimides with N-Boc imines was successfully performed using a bifunctional squaramide-type organocatalyst derived from quinine, affording the corresponding Mannich adduct with two contiguous stereocenters in high yields (up to 98%) with high diastereoselectivities (up to >20:1 dr) and excellent enantioselectivities (up to 99% ee). This protocol provides a direct approach to prepare chiral succinimide derivatives from simple starting material. Density Functional Theory (DFT) calculations with conformational search using an autosampling program revealed that the enantioselectivity profile was dominated by the deformation of the organocatalyst.
The Journal of organic chemistry, 04 Apr. 2025, [Reviewed] - Unraveling the unfolding mechanism of pseudoazurin: Insights into stabilizing cupredoxin fold as a common domain of Cu-containing proteins.
Takahide Yamaguchi; Attila Taborosi; Kiyokazu Tsugane; Kathleen Wood; Andrew E Whitten; Seiji Mori; Takamitsu Kohzuma, Understanding protein unfolding mechanisms is crucial for comprehending protein-folding related diseases, developing diagnostic methods, and designing proteins with desired stability for medicinal or industrial applications. However, investigating structures at atomic resolution is often difficult due to the flexibility and transiency of unfolding intermediate states. Pseudoazurin (PAz) is a well-characterized simple cupredoxin composed of a small polypeptide (124 amino acids) and a single metal cofactor (Cu2+), making it suitable to study the unfolding mechanism. In this study, combining the merits of structure determination by small-angle neutron scattering (SANS) and molecular dynamics (MD) simulations enabled us to access the details of the unfolding mechanism. The unfolding of PAz proceeds through a two-step mechanism involving the "native", "open-domain", and "random-coil" states. Several amino acid residues at the vicinity of Cu2+ ion are involved in the structural transitions, where the interactions among these residues are important in controlling the stability of PAz. These findings may be applicable to stabilizing metalloproteins with cupredoxin domain structures.
Journal of inorganic biochemistry, 02 Apr. 2025 - Decomposition Analysis for Visualization of Noncovalent Interactions Based on the Fragment Molecular Orbital Method.
Dmitri G Fedorov; Diego Inostroza; Bastien Courbiere; Fréderic Guegan; Julia Contreras-García; Seiji Mori, Many-body expansions of the electron density and Fock matrix in the fragment molecular orbital method (FMO) are used to reveal the role of polarization and charge transfer on noncovalent interactions (NCI). In addition to the physicochemical insight gained from these analyses, the use of FMO permits a rapid evaluation of electron densities to study NCI. The developed method is applied to a solvated sodium cation and a small polypeptide, validating the accuracy of the approach with respect to full calculations and revealing the role of polarization and charge transfer in NCI. In order to show the full potential of the approach, the FMO/NCI method is applied to a complex of the Trp-cage (PDB: 1L2Y) protein with a ligand, delivering fruitful insights into binding from both density and energy perspectives. NCI is shown to provide a comprehensive visual picture of interactions that might be missed without it, in particular, interactions between functional groups in a fragment.
Journal of chemical theory and computation, 19 Feb. 2025, [Reviewed] - Enantioselective Synthesis of Chiral Ferrocenyl Aminoalcohols: Simultaneous Induction of Multiple Types of Chirality by a Rhodium-Catalyzed Asymmetric Ring-Opening Strategy.
Takamu Isoda; Komei Jimba; Kyohei Kawashima; Takahiro Nishinoiri; Seiji Mori; Akihiro Tsurusaki; Ken Kamikawa, Chiral ferrocenyl aminoalcohols were enantioselectively synthesized via the rhodium-catalyzed asymmetric aminative ring- opening of 1,4-epoxy-1,4-dihydronaphthalenylferrocenes. A planar chiral phosphine-olefin ligand consisting of a cyclopentadienyl (Cp) manganese scaffold provided excellent catalytic performance, furnishing the ring-opening products in high yield and enantioselctivity (up to 99:1 enantiomeric ratio (e.r.)). The enantioselectivity could be further improved by changing the steric congestion in the cyclopentadienyl unit of the ferrocenyl fragment of the starting 1,4-epoxy-1,4-dihydronaphthalenylferrocene. Density functional theory (DFT) calculations confirmed the high enantioselective induction in the ring-opening reaction, estimating an e.r. of 99:1, which is in excellent agreement with the experimental results. The application of the thus obtained chiral ferrocenyl aminoalcohols as ligands in asymmetric reactions was also investigated.
Angewandte Chemie (International ed. in English), 05 Feb. 2025, [Reviewed] - Aggregation-induced enhanced fluorescence emission of chiral Zn(II) complexes coordinated by Schiff-base type binaphthyl ligands.
Daiki Tauchi; Katsuya Kanno; Masashi Hasegawa; Yasuhiro Mazaki; Kazunori Tsubaki; Ken-Ichi Sugiura; Takuya Shiga; Seiji Mori; Hiroyuki Nishikawa, A pair of novel chiral Zn(II) complexes coordinated by Schiff-base type ligands derived from BINOL (1,1'-bi-2-naphthol), R-/S-Zn, were synthesized. X-ray crystallography revealed the presence of two crystallographically independent complexes; one has a distorted trigonal-bipyramidal structure coordinated by two binaphthyl ligands and one disordered methanol molecule (molecule A), while the other has a distorted tetrahedral structure coordinated by two binaphthyl ligands (molecule B). Numerous CH⋯π and CH⋯O interactions were identified, contributing to the formation of a 3-dimensional rigid network structure. Both R-/S-Zn exhibited fluorescence in both CH2Cl2 solutions and powder samples, with the photoluminescence quantum yields (PLQYs) of powder samples being twice as large as those in solutions, indicating aggregation-induced enhanced emission (AIEE). The AIEE properties were attributed to the restraint of the molecular motion arising from the 3-dimensional intermolecular interactions. CD and CPL spectra were observed for R-/S-Zn in both solutions and powders. The dissymmetry factors, gabs and gCPL values, were within the order of 10-3 to 10-4 magnitudes, comparable to those reported for chiral Zn(II) complexes in previous studies.
Dalton transactions (Cambridge, England : 2003), 28 May 2024 - Asymmetric Cross Couplings of Trifluoromethyl Radical to Vinylarenes with N-Hydroxy-oxazinediones and Subsequent Aerobic Oxidative Homocoupling of 2-Naphthols Catalysed by Chiral Vanadyl Complexes
Chien-Tien Chen; Shiang-Fu Hung; Bang-You Tsai; Tsung-Cheng Chen; Chien-I Lein; Pin-Xuan Tseng; Yu-Chang Chang; Chin-Wei Chuang; Rachit Agarwal; Chan-Wei Hsu; Yuto Shimizu; Ryoma Fujii; Seiji Mori, Last, Wiley-VCH
Advanced Synthesis & Catalysis, 27 Nov. 2023, [Reviewed] - 〔Major achievements〕Theoretical Investigations of Palladium-Catalyzed [3+2] Annulation via Benzylic and meta C−H Bond Activation
Theoretical Investigations of Palladium-Catalyzed [3+2] Annulation via Benzylic and meta C-H Bond Activation, Last, Abstract
The palladium‐catalyzed reaction of aromatic amides with maleimides results in the formation of a double C−H bond activation product, which occurs at both the benzylic and meta positions. Computational chemistry studies suggest that the first C−H bond activation unfolds via a six‐membered palladacycle, maleimide insertion, protonation of the Pd−N bond, and then activation of the meta C−H bond. The process concludes with reductive elimination, producing an annulation product. The energy decomposition analysis (EDA) showed that the deformation energy favors the ortho C−H bond activation process. However, this route is non‐productive. The interaction energy controls the site where the maleimide is inserted into the Pd−C(sp3) bond, which determines its site selectivity. The energetic span model indicates that the meta C−H bond activation step is the one that determines the turnover frequency. Regarding the directing group, it has been concluded that the strong Pd−S bonding and the destabilizing effect of the deformation energy allow the 2‐thiomethylphenyl to function effectively as a directing group., Wiley
Chemistry-An Asian Journal, 03 Aug. 2023, [Reviewed], [Invited] - Systematic elucidation of the second coordination sphere effect on the structure and properties of a blue copper protein, pseudoazurin
Takahide Yamaguchi; Attila Taborosi; Chihiro Sakai; Kohei Akao; Seiji Mori; Takamitsu Kohzuma, Elsevier
Journal of Inorganic Biochemistry, 15 Jun. 2023, [Reviewed] - Incorporation of a bromine atom into DNA-related molecules changes their electronic properties
Misaki Hirato; Akinari Yokoya; * Yuji Baba; Seiji Mori; Kentaro Fujii; Shin-ichi Wada; Yudai Izumi; and Yoshinori Haga, To understand the mechanism underlying the high radio-sensitisation of living cells possessing brominated genomic DNA, X-ray photoelectron spectroscopy (XPS) using synchrotron X-rays with energies of 2000 or 2500 eV was used to study brominated and nonbrominated nucleobases, nucleosides and nucleotides. The bromine atom significantly reduced the energy gap between the valence and conduction states, although the core level states were not greatly affected. This finding was supported by quantum chemical calculation for the nucleobases and nucleosides. Our findings strongly indicate that the energy gaps between the valence and conduction levels of the molecules are significantly reduced by bromination. Furthermore, the brominated molecules are more likely to produce inelastic scattering low energy electrons upon exposure to 2000 or 3000 eV X-rays. This modification of electronic properties around the brominated group may both facilitate electron transfer to the brominated site in DNA and increase the probability of reaction with low energy electrons. These processes can induce DNA damage, presumably resulting in debromination of the uracil moiety and a subsequent cytotoxic effect., RSC publisher
Physical Chemistry Chemical Physics, 11 May 2023, [Reviewed] - Experimental and theoretical studies of the rhodium(I)-catalysed C-H oxidative alkenylation/cyclization of N-(2-(methylthio)phenyl)benzamides with maleimides
Aymen SKHIRI; Attila Taborosi; Nozomi Ohara; Yusuke Ano; Seiji Mori; * and Naoto Chatani*, Corresponding, Royal Society of Chemistry
Organic Chemistry Frontiers, 13 Feb. 2023, [Reviewed] - Neutron crystallography and quantum chemical analysis of bilin reductase PcyA mutants reveal substrate and catalytic residue protonation states
Tatsuya Joutsuka; Ryota Nanasawa; Keisuke Igarashi; Kazuki Horie; Masakazu Sugishima; Yoshinori Hagiwara; Kei Wada; Keiichi Fukuyama; Naomine Yano; Seiji Mori; Andreas Ostermann; Katsuhiro Kusaka; Masaki Unno, Elsevier BV
Journal of Biological Chemistry, 01 Dec. 2022, [Reviewed] - Non-innocent redox behavior of CuII–p-dimethylaminophenolate complexes: formation and characterization of the CuI–phenoxyl radical species
Yuto Shima; Takashi Suzuki; Hitoshi Abe; Tatsuo Yajima; Seiji Mori and Yuichi Shimazaki, Cu complexes with p-dimethylaminophenolate ligands were synthesized by the reaction of Cu-II ions with the ligands under inert gas atmosphere and characterized. The complexes showed a valence state change from Cu-II-phenolate to Cu-I-phenoxyl radical on loss of the coordinated solvent. The Cu-I-phenoxyl radical species showed the characteristic properties and reactivities., Royal Society of Chemistry
Chem.Commun., 04 May 2022, [Reviewed] - Iridium(III)-Catalyzed Asymmetric Site-Selective Carbene C–H Insertion during Late-Stage Transformation
Yuki Yamakawa; Takashi Ikuta; Hiroki Hayashi; Keigo Hashimoto; Ryoma Fujii; Kyohei Kawashima; Seiji Mori; Tatsuya Uchida*; and Tsutomu Katsuki
The Journal of Organic Chemistry, 03 May 2022, [Reviewed] - Lanostane triterpenoids from cultivated fruiting bodies of basidiomycete Ganoderma mbrekobenum
44.Arunrat Yangchum; Ryoma Fujii; Wilunda Choowong; Pranee Rachtawee; Maneerat Pobkwamsuk; Thitiya Boonpratuang; Seiji Mori; Masahiko Isaka
Phytochemistry, 01 Apr. 2022, [Reviewed] - Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions
Naoki Sakai; Kohei Ojima; Seiji Mori*; and Takeshi Oriyama*, Corresponding, American Chemical Society
The Journal of Organic Chemistry, 24 Feb. 2022, [Reviewed] - 〔Major achievements〕Reaction Path Determination of Rhodium(I)-Catalyzed C–H Alkylation of N-8-Aminoquinolinyl Aromatic Amides with Maleimides
Attila Taborosi; Oiyuan He; Yusuke Ano; Naoto Chatani; Seiji Mori, Corresponding, ACS Publications
The Journal of Organic Chemistry, 28 Dec. 2021, [Reviewed] - Solid State Characterization of One- and Two-Electron Oxidized CuII-salen Complexes with para-Substituents: Geometric Structure-Magnetic Property Relationship
Tomoyuki Takeyama; Takashi Suzuki; Misa Kikuchi; Misato Kobayashi; Hiromi Oshita; Kyohei Kawashima; Seiji Mori; Hitoshi Abe; Norihisa Hoshino; Satoshi Iwatsuki; Yuichi Shimazaki, Wiley
European Journal of Inorganic Chemistry, 05 Oct. 2021, [Reviewed] - H/D Isotope Effects in Keto-Enol Tautomerism of β-Dicarbonyl Compounds —Importance of Nuclear Quantum Effects of Hydrogen Nuclei—
Taro Udagawa; * Rhys B. Murphy; Tamim A. Darwish; Masanori Tachikawa; * and Seiji Mori *, Last, Deuterium isotope effects in the keto-enol tautomerism of β-dicarbonyl compounds (malonaldehyde, acetylacetone, dibenzoylmethane, and avobenzone) have been studied using a B3LYP+D functional level of multi-component density functional theory (MC_DFT), which can directly take nuclear quantum effects (NQEs) of the hydrogen nuclei into account. We clearly show that the keto-enol energy difference becomes smaller by deuterium substitution, which is in reasonable agreement with the corresponding experimental evidence. Our MC_DFT study also reveals the hydrogen/deuterium (H/D) isotope effect in geometries and shows that the deuterium substitution weakens the intramolecular hydrogen-bonded interaction in the enol form. Direct treatment of NQEs of hydrogen nuclei via the MC_DFT method is essential for analyzing the H/D isotope effect in keto-enol tautomerism of β-dicarbonyl compounds. Such isotope effects cannot be reproduced in the conventional DFT scheme with harmonic zero-point vibrational corrections., Chemical Society of Japan
Bulletin of the Chemical Society of Japan, 11 Aug. 2021, [Reviewed] - Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α-Aminomaleimides to β-Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid
Naoki Sakai; Kyohei Kawashima; Masashi Kajitani; Seiji Mori; and Takeshi Oriyama, Corresponding, American Chemical Society
Organic Letters, 13 Jul. 2021, [Reviewed] - Calculation of CYP450 protein–ligand binding and dissociation free energy paths
Kuan-Hsuan Su; Chin-Teng Wu; Shang-Wei Lin; Seiji Mori; Wei-Min Liu; and Hsiao-Ching Yang
The Journal of Chemical Physics, 09 Jul. 2021, [Reviewed], [Invited] - 〔Major achievements〕Enantioselective Radical Type, 1,2-Oxytrifluoromethylation of Olefins Catalyzed by Chiral Vanadyl Complexes: Importance of Noncovalent Interactions
Chien-Tien Chen*; Yu-Cheng Su; Chia-Hao Lu; Chien-I Lien; Shiang-Fu Hung; Chan-Wei Hsu; Rachit Agarwal; Ramuasagar Modala; Hung-Min Tseng; Pin-Xuan Tseng; Ryoma Fujii; Kyohei Kawashima; and Seiji Mori*, Last
ACS Catalysis, 04 Jun. 2021, [Reviewed] - 〔Major achievements〕Combined MD and QM/MM Investigations of Hydride Reduction of 5α-Dihydrotestosterone Catalyzed by Human 3α-Hydroxysteroid Dehydrogenase Type 3: Importance of Noncovalent Interactions
Hiroaki Mitsuizumi; Seiji Mori, Last, American Chemical Society
The Journal of Physical Chemistry B, 09 May 2021, [Reviewed], [Invited] - Front Cover Picture: Iridium‐Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen‐Bonding and sp3‐C−H Noncovalent Interactions (Adv. Synth. Catal. 21/2020)
Hiroaki Murayama; Yoshito Heike; Kosuke Higashida; Yohei Shimizu; Nuttapon Yodsin; Yutthana Wongnongwa; Siriporn Jungsuttiwong; Seiji Mori; Masaya Sawamura, Wiley
Advanced Synthesis & Catalysis, 15 Sep. 2020 - Highly Modified Lanostane Triterpenes from the Wood-Rot Basidiomycete Ganoderma colossus: Comparative Chemical Investigations of Natural and Artificially Cultivated Fruiting Bodies and Mycelial Cultures
Masahiko Isaka*; Panida Chinthanom; Rattaket Choeyklin; Tuksaporn Thummarukcharoen; Pranee Rachtawee; Malipan Sappan; Kitlada Srichomthong; Ryoma Fujii; Kyohei Kawashima; and Seiji Mori, Last, American Chemical Society
Journal of Natural Products, 08 Jul. 2020, [Reviewed] - Iridium‐Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen‐Bonding and sp3‐C–H Noncovalent Interactions
Hiroaki Murayama; Yoshito Heike; Kosuke Higashida; Yohei Shimizu; Nuttapon Yodsin; Yutthana Wongnongwa; Siriporn Jungsuttiwong; Seiji Mori; Masaya Sawamura, Corresponding, Wiley-VCH
Advanced Synthesis & Catalysis, 23 Jun. 2020, [Reviewed] - Importance of Non-Covalent Interactions in Synthetic Organic Chemistry and,Coordination Chemistry
森 聖治; 川島恭平, Lead, 理論化学会
フロンティア, Apr. 2020, [Reviewed], [Invited] - Vanadyl Species-Catalyzed 1, 2-Oxidative Trifluoromethylation of Unactivated Olefins
Chien-Tien Chen*; Ya-Pei Chen; Bang-You Tsai; Yi-Ya Liao; Yu-Cheng Su; Tsung-Cheng Chen; Chia-Hao Lu; Ryoma Fujii; Kyohei Kawashima; Seiji Mori*, Last, American Chemical Society
ACS Catalysis, 21 Feb. 2020, [Reviewed] - Benzophenone and chromone derivatives and their dimers from the scale-insect pathogenic fungus Orbiocrella petchii BCC 51377
Masahiko Isaka; Somporn Palasarn; WilundaChoowong; Kyohei Kawashima; SeijiMori; Suchada Mongkolsamrit; Donnay; Thanakitpipattana
Tetrahedron, 08 Nov. 2019, [Reviewed] - Design and characterization of a 2-(2-hydroxyphenyl)benzimidazole-based Sr2+-selective fluorescent probe in organic and micellar solution systems
Kazuhiro Akutsu-Suyama; Seiji Mori and Takayasu Hanashima, Royal Society of Chemistry
Photochemical & Photobiological Sciences, 03 Sep. 2019, [Reviewed] - The effect of pi-pi stacking interaction of the indole ring with the coordinated phenoxyl radical in a nickel (II)-salen type complex. Comparison with the corresponding Cu(II) complex
Hiromi Oshita; Takashi Suzuki; Kyohei Kawashima; Hitoshi Abe; Fumito Tani; Seiji Mori; Tatsuo Yajima; Yuichi Shimazaki, In order to gain new insights into the effect of the pi-pi stacking interaction of the indole ring with the phenoxyl radical moiety as seen in the active form of galactose oxidase, we have prepared Ni(s) complexes of a methoxy substituted salen-type ligand containing a pendent indole ring on the dinitrogen chelate backbone and characterized their one-electron oxidized forms. The X-ray crystal structure analysis and the other physicochemical experiments of the Ni(s) complex revealed no significant intramolecular interaction of the indole ring with the coordination plane. On the other hand, the X-ray crystal structures of the oxidized Ni(ii) complex exhibited the pi-pi stacking interaction of the indole ring mainly with one of the two phenolate moieties. While the phenoxyl radical electron was delocalized on the two phenolate moieties in the Ni(s)-salen coordination plane, the phenolate moiety in close contact with the indole moiety was considered to be the initial oxidation locus, indicating that the indole ring interacted with the phenoxyl radical by pi-pi stacking. The UV vis NIR spectrum of the oxidized Ni(ii) complex with the pendent indole ring was different from that of the complex without the side chain indole ring, but the differences were rather small in comparison with the oxidized Cu(ii)-salen complexes with the pi-pi stacking interaction of the indole ring. Such differences are due to the electronic structure difference, the localized radical electron on one of the phenolate moieties in the oxidized Cu(ii) complexes being more favorable for then pi-pi stacking interaction., ROYAL SOC CHEMISTRY
DALTON TRANSACTIONS, Aug. 2019, [Reviewed] - pi-pi Stacking Interaction in an Oxidized Cu-II-Salen Complex with a Side-Chain Indole Ring: An Approach to the Function of the Tryptophan in the Active Site of Galactose Oxidase
Hiromi Oshita; Takashi Suzuki; Kyohei Kawashima; Hitoshi Abe; Fumito Tani; Seiji Mori; Tatsuo Yajima; Yuichi Shimazaki, In order to gain new insights into the effect of the pi-pi stacking interaction of the indole ring with the Cu-II-phenoxyl radical as seen in the active form of galactose oxidase, we have prepared a Cu-II complex of a methoxy-substituted salen-type ligand, containing a pendent indole ring on the dinitrogen chelate backbone, and characterized its one-electron-oxidized forms. The X-ray crystal structures of the oxidized Cu-II complex exhibited the pi-pi stacking interaction of the indole ring mainly with one of the two phenolate moieties. The phenolate moiety in close contact with the indole moiety showed the characteristic phenoxyl radical structural features, indicating that the indole ring favors the pi-pi stacking interaction with the phenoxyl radical. The UV/Vis/NIR spectra of the oxidized Cu-II complex with the pendent indole ring was significantly different from those of the complex without the side-chain indole ring, and the absorption and CD spectra exhibited a solvent dependence, which is in line with the phenoxyl radical-indole stacking interaction in solution. The other physicochemical results and theoretical calculations strongly support that the indole ring, as an electron donor, stabilizes the phenoxyl radical by the pi-pi stacking interaction., WILEY-V C H VERLAG GMBH
CHEMISTRY-A EUROPEAN JOURNAL, Jun. 2019, [Reviewed] - Cavity Closure of 2-Hydroxypropyl-β-Cyclodextrin: Replica Exchange Molecular Dynamics Simulations
Khanittha Kerdpol; Jintawee Kicuntod; Peter Wolschann; Seiji Mori; Chompoonut Rungnim; Manaschai Kunaseth; Hisashi Okumura; Nawee Kungwan; and Thanyada Rungrotmongkol, MDPI
Polymers, 16 Jan. 2019, [Reviewed] - Theoretical investigations of Rh‐catalyzed asymmetric 1, 4‐addition to enones using planar‐chiral phosphine‐olefin ligands
Kyohei Kawashima; Takehiro Sato; Masamichi Ogasawara; Ken Kamikawa; Seiji Mori, Last, Wiley
Journal of computational chemistry, 05 Jan. 2019, [Reviewed], [Invited] - Recent Advances for Reaction Mechanisms of Metal-Catalyzed Activations of Carbon-Containing Bonds with the Aid of Density Functional Calculations
Seiji Mori, Lead, 錯体化学会
錯体化学会誌, 30 Nov. 2018, [Reviewed], [Invited] - QM/MM Investigation for Protonation States in a Bilin Reductase PcyA‐Biliverdin IXɑ Complex
Eri Iijima M. Paul Gleeson Masaki Unno Seiji Mori, Last, Wiley
ChemPhysChem, 07 Aug. 2018, [Reviewed] - Characterization of the one-electron oxidized Cu(II)-salen complexes with a side chain aromatic ring: the effect of the indole ring on the Cu(II)-phenoxyl radical species
Hiromi Oshita; Takayoshi Yoshimura; Seiji Mori; Fumito Tani; Yuichi Shimazaki; Osamu Yamauchi, To gain insights into the role of the proximal indole ring in the redox-active metal center as seen in galactose oxidase, we prepared the Cu(II)-salen-type complexes having a pendent indol-3-ylmethyl (1), methyl (2) or benzyl (3) group substituted on the ethylenediamine moiety and investigated the structures and redox properties by various physicochemical methods and theoretical calculations. Neutral complexes 1, 2, and 3 showed no significant difference in the UV-Vis-NIR and EPR spectra. One-electron oxidation of 1, 2, and 3 by addition of 1 equiv. of thianthrenyl radical gave [1]SbCl (6) , [2]SbCl (6) , and [3]SbCl (6) , respectively, which could be assigned to relatively localized phenoxyl radical species. The cyclic and differential pulse voltammograms of [1]SbCl (6) showed two redox waves with a large separation between the first and second redox potentials compared with the separations observed for [2]SbCl (6) and [3]SbCl (6) . This suggests that [1]SbCl (6) is more stabilized than [2]SbCl (6) and [3]SbCl (6) . The NIR band of [1]SbCl (6) showed a larger blue shift than that of [2]SbCl (6) and [3]SbCl (6) . The EPR spectrum of [2]SbCl (6) exhibited an intense signal at the g value of 2 due to partial disproportionation to form the EPR active two-electron oxidized complex [2] (2+) , while the EPR intensity of [1]SbCl (6) was much weaker than that of [2]SbCl (6) . These results indicate that the pendent indole moiety stabilizes the Cu(II)-phenoxyl radical in [1]SbCl (6) most probably by stacking with the phenoxyl moiety, which is further supported by DFT calculations., SPRINGER
JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, Jan. 2018, [Reviewed], [Invited] - Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH⋯O/sp3-CH⋯O two-point hydrogen bonding combined with dispersive attractions
Martin C. Schwarzer; Akane Fujioka; Takaoki Ishii; Hirohisa Ohmiya; Seiji Mori; Masaya Sawamura, Copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes with chiral prolinol-phosphine ligands, most preferably (αR,2S)-1-(2-dicyclohexylphosphinobenzyl)-α-neopentyl-2-pyrrolidinemethanol, afforded various enantioenriched chiral propargylic tertiary alcohols. Quantum-chemical calculations using the BP86 density functional including Grimme's empirical dispersion correction [DF-BP86-D3(BJ)-PCM(tBuOH)/TZVPP//DF-BP86-D3(BJ)/SVP] show the occurrence of OH⋯O/sp3-CH⋯O two-point hydrogen bonding between the chiral ligand and the carbonyl group of the ketoester in the stereo-determining transition states. Combined with the hydrogen-bonding interactions orienting the ketoester substrate, dispersive attractions between the chiral ligand (P-cyclohexyl groups) and the ketoester in the favored transition states, rather than steric repulsions in the disfavored transition state explain the enantioselectivity of the asymmetric copper catalysis., Royal Society of Chemistry
Chemical Science, 2018, [Reviewed] - Characterization of Group 10-Metal-p-Substituted Phenoxyl Radical Complexes with Schiff Base Ligands.
Hiromi Oshita; Misa Kikuchi; Kaoru Mieda; Takashi Ogura; Takayoshi Yoshimura; Fumito Tani; Tatsuo Yajima; Hitoshi Abe; Seiji Mori; Yuichi Shimazaki, Methylthiophenoxyl radical plays an important role as the active form of galactose oxidase (GO), which catalyzes oxidation of a primary alcohol to the corresponding aldehyde. Although many metal(II)-phenoxyl radical species have been reported, only a few studies have been reported on the properties of methylthiophenoxyl radical-metal complexes. We have prepared the group 10 metal (Ni, Pd and Pt) complexes of a salen-type ligand with a methylthio group at para-position of the two phenolate moieties and characterized them by X-ray crystal structure analyses and various spectroscopic methods in order to understand the role of the methylthio moiety in phenoxyl radical metal complexes. The corresponding pmethoxy substituted derivatives have been also characterized for comparison. All the one-electron oxidized group 10 metal methylthiophenolate complexes have a relatively localized radical site on one of the two phenolate moieties in comparison to the one-electron oxidized complexes of pmethoxy derivatives and exhibit different properties dependent on the central metal ions., WILEY-V C H VERLAG GMBH
CHEMISTRYSELECT, Oct. 2017, [Reviewed] - Combined Theoretical and Experimental Studies of Nickel-Catalyzed Cross-Coupling of Methoxyarenes with Arylboronic Esters via C-O Bond Cleavage
Martin C. Schwarzer; Ryosuke Konno; Takayulu Hojo; Alumichi Ohtsuki; Keisuke Nakamura; Ayaka Yasutome; Hiroaki Takahashi; Toshiaki Shimasaki; Mamoru Tobisu; Naoto Chatani; Seiji Mori, Nickel(0)-catalyzed cross-coupling of methoxyarenes through C-O bond activation has been the subject of considerable research because of their favorable features compared with those of the cross-coupling of aryl halides, such as atom economy and efficiency. In 2008, we have reported nickel/PCy3-catalyzed cross-coupling of methoxyarenes with arylboronic esters in which the addition of a stoichiometric base such as CsF is essential for the reaction to proceed. Recently, we have also found that the scope of the substrate in the Suzuki Miyaura-type cross-coupling of methoxyarenes can be greatly expanded by using 1,3-dicyclohexylimidazol-2-ylidene (ICy) as the ligand. Interestingly, a stoichiometric amount of external base is not, required for the nickel/ICy-catalyzed cross-coupling. For the mechanism and origin elucidated, density functional theory calculations are conducted. In the nickel/PCy3-catalyzed reactions, the activation energy for the oxidative addition of the Caryl)-OMe bond is too high to occur under the catalytic conditions. However, the oxidative addition process becomes energetically feasible when CsF and an arylboronic ester interact with a Ni(PCy3)(2)/methoxyarene fragment to form a quaternary complex. In the nickel/ICy-catalyzed reactions, the oxidative addition of the Caryl)-OMe bond can proceed more easily without the aid of CsF because the nickel-ligand bonds are stronger and therefore stabilize the transition state. The subsequent transmetalation from an Ar-Ni-OMe intermediate is determined to proceed through a pathway with lower energies than those required for beta-hydrogen elimination. The overall driving force of the reaction is the reductive elimination to form the carbon carbon bond., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Aug. 2017, [Reviewed] - Asymmetric Synthesis of beta-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with a Prolinol-Phosphine Chiral Ligand
Yurie Takayama; Takaoki Ishii; Hirohisa Ohmiya; Tomohiro Iwai; Martin C. Schwarzer; Seiji Mori; Tohru Taniguchi; Kenji Monde; Masaya Sawamura, Prolinol-phosphine chiral ligands enabled highly enantioselective copper-catalyzed intermolecular alkyne-nitrone coupling (Kinugasa reaction) to produce 1,3,4-trisubstituted chiral beta-lactams. A high level of enantiocontrol was achieved not only with aryl-or alkenylacetylenes but also with alkylacetylenes, which were important but unfavorable substrates in the previously reported protocols. Two-point hydrogen bonding between the chiral ligand and the nitrone oxyanion consisting of O-H center dot center dot center dot O and C(sp(3)) H center dot center dot center dot O hydrogen bonds is proposed., WILEY-V C H VERLAG GMBH
CHEMISTRY-A EUROPEAN JOURNAL, Jun. 2017, [Reviewed] - Exploring the full catalytic cycle of rhodium(I)BINAP-catalysed isomerisation of allylic amines: a graph theory approach for path optimisation
Takayoshi Yoshimura; Satoshi Maeda; Tetsuya Taketsugu; Masaya Sawamura; Keiji Morokuma; Seiji Mori, We explored the reaction mechanism of the cationic rhodium(I)-BINAP complex catalysed isomerisation of allylic amines using the artificial force induced reaction method with the global reaction route mapping strategy, which enabled us to search for various reaction paths without assumption of transition states. The entire reaction network was reproduced in the form of a graph, and reasonable paths were selected from the complicated network using Prim's algorithm. As a result, a new dissociative reaction mechanism was proposed. Our comprehensive reaction path search provided rationales for the E/Z and S/R selectivities of the stereoselective reaction., ROYAL SOC CHEMISTRY
CHEMICAL SCIENCE, Jun. 2017, [Reviewed] - Investigation of substitution effect on fluorescence properties of Zn2+-selective ratiometric fluorescent compounds: 2-(2 '-Hydroxyphenyl)benzimidazole derivatives
Kazuhiro Akutsu; Seiji Mori; Kenichi Shinmei; Hiroki Iwase; Yoshiharu Nakano; Yuki Fujii, 2-(2'-Hydroxyphenyl)benzimidazole derivatives (X-HBIs), modified by various substituents X (X=H, CH3, OH, OCH3, NO2, NHCOCH3, NH2, N(CH3)(2)), were synthesized and their fluorescent behaviors and equilibriums in aqueous solution were studied. Strong fluorescence attributed to the tautomer emission was observed in aqueous solution at pH 7.4. The fluorescence intensities of the X-HBIs were enhanced selectively by addition of Zn2+ but not by addition of Na+, K+, Mg2+, Ca2+, Mn2+, Fe2+, Co2+, Ni2+, and Cu2+. Additionally, the effective ratiometric fluorescence response to Zn2+ addition was observed in 5-NH2-HBI and 5-N(Me)(2)-HBI. The pH-titration and speciation studies proved that the X-HBIs have two or three protonation equilibriums and one complexation equilibrium corresponding to the formation of the [Zn(X-HBI)](+) complex. Further structural studies using extended X-ray absorption fine structure analyses and density functional theory calculations identified the dominant Zn2+ species as the [Zn(HBI)(H2O)(3)](+) complex in aqueous solution. Based on the substituent effect on the fluorescence properties of X-HBIs and their Zn2+ complexes in aqueous solution, the maximum fluorescence excitation and fluorescence wavelengths of both the tautomeric form and the Zn2+ complexes were dependent on the Hammett substituent constants of X, which was attributed to the change of the pi-pi* energy gap of HBI by introduction of the substituent (C) 2015 Elsevier B.V. All rights reserved., ELSEVIER SCIENCE BV
TALANTA, Jan. 2016, [Reviewed] - The molecular mechanism of palladium-catalysed cyanoesterification of methyl cyanoformate onto norbornene
Takuya Ishitsuka; Yasuhiro Okuda; Robert K. Szilagyi; Seiji Mori; Yasushi Nishihara, Potential energy surface mapping was completed for the entire catalytic cycle of palladium-catalysed cyanoesterification onto norbornene (NBE) using density functional theory calculations. We found that after the oxidative addition step of the reagent methyl cyanoformate, the reaction proceeds through an insertion of olefin into a Pd-II-COOMe bond first. Subsequently, reductive elimination occurs by transferring the cyanide group from the Pd center to NBE. This rearrangement is triggered by the rotation of the ester group into a pi-interaction with the Pd-II centre. The regioselectivity of olefin insertion is controlled by ionic and covalent interactions in the precursor pi-complex formation step. Importantly, all of the intermediates and transition states along the exo pathway were found to be more stable than the corresponding structures of the endo pathway without any sign of crossing over between the two surfaces via isomerization. The rate-determining step is the reductive elimination despite the fact that the corresponding activation barrier is reduced by conformational changes via the rotation of a MeOOC-C(NBE) bond., ROYAL SOC CHEMISTRY
DALTON TRANSACTIONS, 2016, [Reviewed] - Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes
Yasuda, Y.; Nagao, K.; Shido, Y.; Mori, S.; Ohmiya, H.; Sawamura, M.
Chemistry - A European Journal, 2015, [Reviewed] - Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
Hojoh, K.; Shido, Y.; Nagao, K.; Mori, S.; Ohmiya, H.; Sawamura, M.
Tetrahedron, 2015, [Reviewed] - Skeletal Rearrangement of Cyano-Substituted Iminoisobenzofurans into Alkyl 2-Cyanobenzoates Catalyzed by B(C6F5)(3)
Jing Li; Yasuhiro Okuda; Jiaji Zhao; Seiji Mori; Yasushi Nishihara, An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate a-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results., AMER CHEMICAL SOC
ORGANIC LETTERS, Oct. 2014, [Reviewed] - Mechanistic insights into the catalytic reaction of plant allene oxide synthase (pAOS) via QM and QM/MM calculations
Tuanjai Somboon; Jun Ochiai; Witcha Treesuwan; M. Paul Gleeson; Supa Hannongbua; Seiji Mori, QM cluster and QM/MM protein models have been employed to understand aspects of the reaction mechanism of plant allene oxide synthase (pAOS). In this study we have investigated two reaction mechanisms for pAOS. The standard pAOS mechanism was contrasted with an alternative involving an additional active site molecule which has been shown to facilitate proton coupled electron transfer (PCET) in related systems. Firstly, we found that the results from QM/MM protein model are comparable with those from the QM cluster model, presumably due to the large active site used. Furthermore, the results from the QM cluster model show that the Fe-III and Fe-IV pathways for the standard mechanism have similar energetic and structural properties, indicating that the reaction mechanism may well proceed via both pathways. However, while the PCET process is facilitated by an additional active site bound water in other related families, in pAOS it is not, suggesting this type of process is not general to all closely related family members. (C) 2014 Elsevier Inc. All rights reserved., ELSEVIER SCIENCE INC
JOURNAL OF MOLECULAR GRAPHICS & MODELLING, Jul. 2014 - Facile Estimation of Catalytic Activity and Selectivities in Copolymerization of Propylene Oxide with Carbon Dioxide Mediated by Metal Complexes with Planar Tetradentate Ligand
Takahiro Ohkawara; Kohei Suzuki; Koji Nakano; Seiji Mori; Kyoko Nozaki, Mechanistic studies were conducted to estimate (1) catalytic activity for PPC, (2) PPC/CPC selectivity, and (3) PPC/PPO selectivity for the metal-catalyzed copolymerization of propylene oxide with carbon dioxide [PPC: poly(propylene carbonate); CPC = cyclic propylene carbonate; PPO: poly(propylene oxide)]. Density functional theory (DFT) studies demonstrated that the Delta G(crb)-Delta G(epx) value should be an effective indicator for the catalytic activities [Delta G(epx): dissociation energy of ethylene oxide from the epoxide-coordinating metal complex; Delta G(crb): dissociation energy of methyl carbonate from the metal carbonate complex]. In addition, metal complexes with a subthreshold Delta G(epx) value were found to show low PPC/CPC selectivity. The PPC/PPO selectivity was related to the Delta G(alk) - Delta G(epx) value and steric environment around the metal center (Delta G(alk): dissociation energy of alkoxide ligand from the metal center). Based on the mechanistic studies, two metal complexes were designed and applied to the copolymerization to support validity of these indicators. The results presented here should be useful for brand-new catalyst candidates since these indicators can be easily calculated by DFT method without computing transition states., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Jul. 2014, [Reviewed] - Redox Chemistry of Nickel(II) Complexes Supported by a Series of Noninnocent beta-Diketiminate Ligands
June Takaichi; Yuma Morimoto; Kei Ohkubo; Chizu Shimokawa; Takayuki Hojo; Seiji Mori; Haruyasu Asahara; Hideki Sugimoto; Nobutaka Fujieda; Nagatoshi Nishiwaki; Shunichi Fukuzumi; Shinobu Itoh, Nickel complexes of a series of beta-diketiminate ligands (L-R(-), deprotonated form of 2-substituted N-[3-(phenylamino)allylidene]aniline derivatives (LH)-L-R, R = Me, H, Br, CN, and NO2) have been synthesized and structurally characterized. One-electron oxidation of the neutral complexes [Ni-II(L-R(-))(2)] by AgSbF6 or [Ru-III(bpy)(3)](PF6)(3) (bpy = 2,2'-bipyridine) gave the corresponding metastable cationic complexes, which exhibit an EPR spectrum due to a doublet species (S = 1/2) and a characteristic absorption band in near IR region ascribable to a ligand-to-ligand intervalence charge-transfer (LLIVCT) transition. DFT calculations have indicated that the divalent oxidation state of nickel ion (Ni-II) is retained, whereas one of the beta-diketiminate ligands is oxidized to give formally a mixed-valence complex, [Ni-II(L-R(-))(L-R(center dot))](+). Thus, the doublet spin state of the oxidized cationic complex can be explained by taking account of the antiferromagnetic interaction between the high-spin nickel(11) ion (S = I) and the organic radical (S = 1/2) of supporting ligand. A single-crystal structure of one of the cationic complexes (R = H) has been successfully determined to show that both ligands in the cationic complex are structurally equivalent. On the basis of theoretical analysis of the LLIVCT band and DFT calculations as well as the crystal structure, the mixed-valence complexes have been assigned to Robin Day class III species, where the radical spin is equally delocalized between the two ligands to give the cationic complex, which is best described as [Ni-II(L-R(0.5 center dot-))(2)](+). One-electron reduction of the neutral complexes with decamethylcobaltocene gave the anionic complexes when the ligand has the electron-withdrawing substituent (R = CN, NO2, Br). The generated anionic complexes exhibited EPR spectra due to a doublet species (S = 1/2) but showed no LLIVCT band in the near-IR region. Thus, the reduced complexes are best described as the d(9) nickel(I) complexes supported by two anionic beta-diketiminate ligands, [Ni-1(L-R(-))(2)](-). This conclusion was also supported by DFT calculations. Substituent effects on the electronic structures of the three oxidation states (neutral, cationic, and anionic) of the complexes are systematically evaluated on the basis of DFT calculations., AMER CHEMICAL SOC
INORGANIC CHEMISTRY, Jun. 2014 - Theoretical Studies of Rhodium-Catalyzed Borylation of Nitriles through Cleavage of Carbon-Cyano Bonds
Hirotaka Kinuta; Hiroaki Takahashi; Mamoru Tobisu; Seiji Mori; Naoto Chatani, Rhodium(I)-catalyzed borylation of nitriles is investigated theoretically, using the density functional theory method, to clarify the reaction mechanism, including the formation process of the catalytically active species, carbon-carbon bond cleavage, and the effect of an amine additive. The initial step in this reaction is the formation of a borylrhodium(I) species, in which the rhodium center carries a significant negative charge. The most energetically favorable pathway for carbon-carbon bond cleavage involves the insertion of a cyano group into borylrhodium(I) to form an iminoacyl intermediate, followed by extrusion of boryl isocyanide (iminoacyl mechanism). The calculation suggests that DABCO can react with coproduced reactive boron species, such as boryl chloride and boryl isocyanide, to form stable adducts, lowering the energy of the entire reaction system. In addition, the chemoselectivities among C-CN, C-Br, and C-Cl bonds observed in experimental studies are in good agreement with the calculated activation energies required for these bond activation processes., CHEMICAL SOC JAPAN
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, Jun. 2014, [Reviewed] - Experimental and Theoretical Studies on the Platinum-Mediated Selective C(sp)-Si Bond Cleavage of Alkynylsilanes
Yasuhiro Okuda; Yuya Ishiguro; Seiji Mori; Kiyohiko Nakajima; Yasushi Nishihara, A series of cis-alkynyl(silyl)platinum(II) complexes was prepared via the chemoselective C(sp)-Si bond cleavage of alkynylsilanes by a platinum(0) complex ligated with the P-N hemilabile bidentate ligand. The coordination of the triple bond to the platinum center triggers selective C(sp) Si bond cleavage. Hammett plots of the P-31{H-1} NMR spectroscopic properties (delta and J values) reflect an electronic effect on platinum(II) complexes; trans substituents of arylethynyl groups are influenced, but cis-positioned silyl groups are not affected, as evidenced by Si-29{H-1} NMR. In comparison, Hammett plots show that C(sp) Si bond cleavage rates are accelerated by electron-rich alkynylsilanes, which is opposite to the ordinary oxidative addition of aryl halides to transition metals often observed in catalytic cross-coupling reactions. A DFT calculation reveals that intermediates and transition states are stabilized by electron-rich alkynylsilanes and that the five-membered hemilabile P-N ligand is essential, in which a reactive electron-deficient 14-electron platinum(0) species is produced via the dissociation of nitrogen, giving rise to a monodentate phosphine coordination. Electron-rich alkynylsilanes allow decreased pi back-donation from the platinum center to the ligand, accelerating the dissociation of the more labile nitrogen. Steric congestion between diisopropylphosphino and silyl groups thermodynamically disfavors C(sp)-Si bond cleavage., AMER CHEMICAL SOC
ORGANOMETALLICS, Apr. 2014, [Reviewed] - The origin of exo-selectivity in methyl cyanoformate addition onto the C=C bond of norbornene in Pd-catalyzed cyanoesterification
Yasuhiro Okuda; Robert K. Szilagyi; Seiji Mori; Yasushi Nishihara, A computational investigation has been carried out to elucidate the origin of the exclusive exo-selectivity in the Pd-catalyzed cyanoesterification of strained cyclic olefins, norbornene and norbornadiene. A hybrid density functional was selected for the level of theory with a triple-zeta quality basis set, which was proposed in an earlier study to provide an experimentally sound ground state electronic structure description for palladium(II) and palladium(IV) complexes from multi-edge X-ray absorption spectroscopic measurements. Given that the product of oxidative addition can be isolated, we focused on the olefin coordination as the earliest possible origin of exo-selectivity. The calculated geometric structure for the trans-Pd(CN)(COOR)(PPh3)(2) complex at the BHandHLYP/ def2TZVP/ PCM(toluene) level is in an excellent agreement with its experimental structure from crystallographic measurements. Upon dissociation of one of its phosphane ligands, the coordinatively unsaturated trans-isomer is only 17 kJ mol(-1) away from the isomerization transition state, leading to the 14-electron cis-isomers that are 17 to 37 kJ mol(-1) lower in energy than the trans-isomers. Regardless of the initial complex for olefin coordination, the exo-isomer for the norbornene complex is at least 8 kJ mol(-1) lower than the corresponding endo-isomer. The origin of this considerable difference in Gibbs free energy can be attributed to the remarkably different steric and agostic hydrogen interactions between the methylene and the ethylene bridges of the norbornene and the adjacent cis-ligands at the Pd-II center., ROYAL SOC CHEMISTRY
DALTON TRANSACTIONS, 2014, [Reviewed] - Cooperative Catalysis of Metal and O-H center dot center dot center dot O/sp(3)-C-H center dot center dot center dot O Two-Point Hydrogen Bonds in Alcoholic Solvents: Cu-Catalyzed Enantioselective Direct Alkynylation of Aldehydes with Terminal Alkynes
Takaoki Ishii; Ryo Watanabe; Toshimitsu Moriya; Hirohisa Ohmiya; Seiji Mori; Masaya Sawamura, Catalyst-substrate hydrogen bonds in artificial catalysts usually occur in aprotic solvents, but not in protic solvents, in contrast to enzymatic catalysis. We report a case in which ligand-substrate hydrogen-bonding interactions cooperate with a transition-metal center in alcoholic solvents for enantioselective catalysis. Copper(I) complexes with prolinol-based hydroxy amino phosphane chiral ligands catalytically promoted the direct alkynylation of aldehydes with terminal alkynes in alcoholic solvents to afford nonracemic secondary propargylic alcohols with high enantioselectivities. Quantum-mechanical calculations of enantiodiscriminating transition states show the occurrence of a nonclassical sp(3)-CHO hydrogen bond as a secondary interaction between the ligand and substrate, which results in highly directional catalyst-substrate two-point hydrogen bonding., WILEY-V C H VERLAG GMBH
CHEMISTRY-A EUROPEAN JOURNAL, Sep. 2013, [Reviewed] - An Efficient Access to Aspermytin A and Oblongolide C through an Intramolecular Nitrile Oxide-Alkene [3+2] Cycloaddition
Atsushi Inoue; Makoto Kanematsu; Seiji Mori; Masahiro Yoshida; Kozo Shishido, The second generation synthesis of (+)-aspermytin A and the first total synthesis of (-)-oblongolide C have been accomplished employing an intramolecular nitrile oxide-alkene [3+2] cycloaddition as the key step., GEORG THIEME VERLAG KG
SYNLETT, Jan. 2013, [Reviewed] - An Osmium(III)/Osmium(V) Redox Couple Generating Os-V(O)(OH) Center for cis-1,2-Dihydroxylation of Alkenes with H2O2: Os Complex with a Nitrogen-Based Tetradentate Ligand
Hideki Sugimoto; Kazuhiro Kitayama; Seiji Mori; Shinobu Itoh, For the synthesis of the 1,2-diols, cis-1,2-dihydroxylation of alkenes catalyzed by osmium(VIII) tetroxide (OsO4) is a powerful method. However, OsO4 is quite toxic due to its highly volatile and sublimable nature. Thus, the development of alternative catalysts for cis-1,2-dihydroxylation of alkenes is highly challenging. Our approach involves the use of a nitrogen-based tetradentate ligand, tris(2-pyridylmethyl)amine (tpa), for an osmium center to develop a new osmium catalyst and hydrogen peroxide (H2O2) as a cheap and environmentally benign oxidant. The new Os tpa complex acts as a very efficient turnover catalyst for syn-selective dihydroxylation of various alkenes (turnover number similar to 4000) in aqueous media, and H2O2 oxidant is formally incorporated into the products quantitatively (100% atom efficiency). The reaction intermediates involved in the catalytic cycle have been isolated and characterized crystallographically as [Os-III(OH)(H2O)(tpa)](2+) and [Os-V(O)(OH)(tpa)](2+) complexes. The observed syn-selectivity, structural characteristics of the intermediates, and kinetic studies have suggested a concerted [3 + 2]-cycloacldition mechanism between [Os-V(O)(OH)(tpa)](2+) and alkenes, which is strongly supported by DFT calculations., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Nov. 2012, [Reviewed] - Quantum chemical studies on the role of water microsolvation in interactions between group 12 metal species (Hg2+, Cd2+, and Zn2+) and neutral and deprotonated cysteines
Seiji Mori; Takahiro Endoh; Yuki Yaguchi; Yuuhei Shimizu; Takayoshi Kishi; Tetsuya K. Yanai, Interactions of group 12 metal(II) species (Hg2+, Cd2+, Zn2+, Hg(H2O) (n) (2+) , Cd(H2O) (n) (2+) , and Zn(H2O) (n) (2+) (n = 1, 2) with neutral (RSH), deprotonated (RS-), and doubly deprotonated cysteine species (abbreviated as "H(2)cys", "Hcys(-)", and "cys(2-)", respectively) are examined with the Becke three-parameter Lee-Yang-Parr (B3LYP) hybrid functional after preliminary screening in a conformation analysis with the Parameterized Model number 3 (PM3) semiempirical method. Effects of water on aqueous solution are evaluated by microsolvation and polarized continuum model (PCM) approaches. In the most stable conformations of M(H(2)cys)(2+) and M(Hcys)(+) complexes (M = Hg2+, Cd2+, and Zn2+), the SH group of the cysteine moiety is already deprotonated and undergoes strong binding with the metal ion. Among Hg(H(2)cys)(2+) complexes, cysteine complexes of Hg2+ without deprotonation of the SH group and mercury(II) carboxylato-type structures are at least 83 and 117 kJ/mol less stable in energy than the most stable complex (B3LYP/6-311++G(d,p)-SDD+d+f//B3LYP/6-31G(d)-SDD+d). Although Zn2+ binds more strongly than Hg2+ to a H(2)cys molecule at the high-level CCSD(T)/6-311++G(d,p)-SDD+d+f//B3LYP/6-311++G(d,p)-SDD+d+f level, [Hg(H2O)(2)](2+) is stronger than [Zn(H2O)(2)](2+) because the deformation of [Zn(H2O)(2)](2+) required to bind to cys is much more than in [Hg(H2O)(2)](2+). Complexes with a deprotonated cysteine, M(Hcys)(+) and M(cys), prefer a multidentate structure., SPRINGER
THEORETICAL CHEMISTRY ACCOUNTS, Oct. 2011, [Invited] - Theoretical studies on model reaction pathways of prostaglandin H-2 isomerization to prostaglandin D-2/E-2
Naoto Yamaguchi; Tatsuya Naiki; Takamitsu Kohzuma; Toshikazu Takada; Fumihiko Sakata; Seiji Mori, Model reaction mechanisms in the biosynthesis of prostaglandin D-2 (PGD(2)) and prostaglandin E-2 (PGE(2)) from prostaglandin H-2 with PGD(2)/E-2 synthase were examined using the ab initio second-order Moller-Plesset perturbation method and density functional theory. The reaction was modeled similar to the isomerization of 2,3-dioxabicyclo[2.2.1] heptane to 3-hydroxycyclopentanone in the presence of MeS-. An explicit solvation of two H2O molecules was also considered, and two probable types of reaction mechanisms were demonstrated. One mechanism starts with proton abstraction from an oxygen-bound carbon at the endoperoxide by a thiolate ion and the other is stepwise and involves attack of a thiolate anion on an oxygen of the endoperoxide group in the first step with protonation of the other oxygen, followed by deprotonation from a carbon-attached oxygen to break an O-S bond to yield PGD(2) or PGE(2). We also found that the mPW1LYP hybrid method was superior to the B3LYP functional for systems with respect to the state-of-the-art CCSD(T) energetics., SPRINGER
THEORETICAL CHEMISTRY ACCOUNTS, Jan. 2011, [Reviewed] - UV resonance Raman studies on the activation mechanism of human hematopoietic prostaglandin D-2 synthase by a divalent cation, Mg2+
Yoshiko Uchida; Yoshihiro Urade; Seiji Mori; Takamitsu Kohzuma, The Mg2+ ion-assisted activation mechanism of the active site Tyr8 of a human hematopoietic prostaglandin D-2 synthase (H-PGDS) was studied by ultraviolet resonance Raman (UVRR) spectroscopy. Addition of Mg2+ to the native H-PGDS at pH 8.0 resulted in the Y8a Raman band of Tyr8 shifting from 1615 cm(-1) to 1600 cm(-1). This large shift to lower energy of the tyrosine Y8a vibrational mode is caused by the deprotonation of the tyrosine phenol group promoted by binding of Mg2+. Upon subsequent addition of glutathione (GSH), the Mg2+/H-PGDS solution showed the Tyr8 Raman band shifted to 1611 cm(-1), which is 11 cm(-1) higher than the frequency of the Mg2+ complex of H-PGDS, but 4 cm(-1) lower than the Mg2+ free enzyme. These UVRR observations suggest that the deprotonated Tyr8 in the presence of Mg2+ is re-protonated by the abstraction of H+ from the thiol group of GSH, and that the re-protonated Tyr8 species forms a hydrogen bond with the thiolate anion of GSH. Density functional theory calculations on several model complexes of p-cresol were also performed, which suggested that the pK(a) and vibrational frequencies of the Tyr8 phenol group are affected by the degree and structure of hydration of the Tyr8 residue. (C) 2009 Elsevier Inc. All rights reserved., ELSEVIER SCIENCE INC
JOURNAL OF INORGANIC BIOCHEMISTRY, Mar. 2010, [Reviewed] - Regioselective Synthesis of Heterocycles Containing Nitrogen Neighboring an Aromatic Ring by Reductive Ring Expansion Using Diisobutyl aluminum Hydride and Studies on the Reaction Mechanism
Hidetsura Cho; Yusuke Iwama; Kenji Sugimoto; Seiji Mori; Hidetoshi Tokuyama, A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic rings with diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an aromatic ring, including indoline, 1,2,3,4,5,6-hexahydrobenz[b]azocine, 3,4-dihydro-2H-benzo[b][1,4]oxazine, 2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine, 1,2,3,4,5,6-hexahydroazepino[3,2-b]-indole, 2,3,4,5-tetrahydro-1H-benzothieno[2,3-b]azepine, 2,3,4,5-tetrahydro-1H-benzothieno[3,2-b]azepine, 5,6-dihydrophenanthridine, and 5,6,11,12-tetrahydrodibenz[b,f]azocine. The reaction mechanism leading to the rearrangement was investigated on the basis of the restricted Becke three-parameter plus Lee-Yang-Parr (B3LYP) density functional theory (DFT) with the 6-31G (d) basis set. It was found that the reaction proceeds through a three-centered transition state via a stepwise mechanism because the potential energy curve along the intrinsic reaction coordinate (IRC) had two maxima (saddle points; TS1 and TS2) and the partial phenonium cation intermediate C. In addition to cyclic ketoximes fused to aromatic rings, the reactions of various cyclic and acyclic ketoximes were examined to investigate preference of migrating group. It was found that the more electron-rich group migrated preferentially to give the corresponding secondary amines., AMER CHEMICAL SOC
JOURNAL OF ORGANIC CHEMISTRY, Feb. 2010, [Reviewed] - 2SC1013 Theoretical analysis for structures and reaction mechanisms of atypical cytochrome P450(2SC Structure and Function of Weak Interaction in Metalloproteins-Protein Field and Highly Organized Specific Reaction,The 48th Annual Meeting of the Biophysical Society of Japan)
Mori Seiji, The Biophysical Society of Japan General Incorporated Association
Seibutsu Butsuri, 2010 - The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of alpha-thio and alpha-selenoketones with ynolates
Takashi Yoshikawa; Seiji Mori; Mitsuru Shindo, Highly Z-selective olefination of acyclic alpha-thio and alpha-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the beta-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the sigma orbital of the C-S bond or a lone pair orbital on the S and sigma* orbitals of the breaking C-O bond, and the sigma orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the sigma* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown. (c) 2009 Elsevier Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
TETRAHEDRON, Oct. 2009, [Reviewed] - Regioselective synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride (DIBAH)
Hidetsura Cho; Yusuke Iwama; Kenji Sugimoto; Seiji Mori; Eunsang Kwon; Hidetoshi Tokuyama
The 23rd International Congress on Heterocyclic Chemistry (ICHC2009), Jul. 2009 - Equilibrium and ab initio computational studies on the adduct formation of 1,3-diketonato-lithium(I), -sodium(I) and -potassium(I) with 1, 10-phenanthroline and its 2,9-dimethyl derivatives
Ken-ichiro Ishimori; Seiji Mori; Yuji Ito; Kousaburo Ohashi; Hisanori Imura, Highly effective and selective synergistic extraction of Li(+) has been found using 2-naphthoyltrifluoroacetone (Hnta) as an acidic chelating agent and 2,9-dimethyl-1,10-phenanthroline (dmp) or 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (dmdpp) as a neutral ligand (denoted as Q in toluene. The synergism was ascribed to the adduct formation in the organic phase, and the composition and the formation constants of the adducts for alkali metal ions (M(+)) were determined by the extraction equilibrium analysis. The adducts found were M(nta)L for Li(+) and Na(+), while M(nta)L and M(nta)L(2) for K(+). To understand thermodynamics of the adduct formation with the bidentate amines, quantum chemical calculations of the 1:1 and 1:2 adduct formations with dmp and 1,10-phenanthroline (phen) were pet-formed. The electronic and steric effects of the methyl groups at 2,9-positions of phen on the thermodynamic functions of adduct formation as well as the high lithium selectivity were quantitatively elucidated. (C) 2009 Elsevier B.V. All rights reserved., ELSEVIER SCIENCE BV
TALANTA, Jun. 2009, [Reviewed] - The Effect of Alkynyl Groups on Torquoselectivity. Highly Stereoselective Olefination of Alkynyl Ketones with Ynolates
Takashi Yoshikawa; Seiji Mori; Mitsuru Shindo, We have shown the first experimental evidence of the alkynyl substituent effect on torquoselectivity and succeeded in effecting the highly torquoselective olefination of alkynyl ketones to provide functionalized tetrasubstituted olefins., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Feb. 2009, [Reviewed] - Theoretical Study of the Cycloaddition Reaction of a Tungsten-Containing Carbonyl Ylide
Kazuta Ito; Yoshihiro Hara; Seiji Mori; Hiroyuki Kusama; Nobuharu Iwasawa, The [3+2] cycloaddition reaction of a tungsten-containing carbonyl ylide with methyl vinyl ether and the insertion reactions of the nonstabilized carbene complex intermediates produced have been investigated through the use of B3LYP density functional theory. The [3+2] cycloaddition reaction of the tungsten-containing carbonyl ylide has been proven to proceed concertedly, reversibly, and with high endo selectivity. The intermolecular Si-H insertion reactions of the carbene complex intermediates have been proven to be favored over the intramolecular C-H insertion, in good agreement with experimental results. Moreover, the kinetic endo/exo ratio of the [3+2] cycloaddition reaction has been shown to determine the endo/exo selectivity of the Si-H insertion products. In addition, secondary orbital interactions involving the benzene ring and the carbonyl ligand on the metal center have turned out to strongly influence the high endo selectivity of the [3+2] cycloaddition reaction with methyl vinyl ether., WILEY-V C H VERLAG GMBH
CHEMISTRY-A EUROPEAN JOURNAL, 2009, [Reviewed] - Density Functional Studies on Isomerization of Prostaglandin H-2 to Prostacyclin Catalyzed by Cytochrome P450
Tetsuya K. Yanai; Seiji Mori, Reaction mechanisms for the isomerization of prostaglandin H-2 to prostacyclin catalyzed by cytochrome P450 are investigated by the unrestricted Becke's three-parameter plus Lee-Yang-Parr density functional level of theory. The results show that the homolytic O-O bond cleavage of endoperoxide in prostaglandin H, is the rate-limiting step and that the isomerization proceeds through proton-coupled electron transfer. We located two reaction pathways through an Fe-IV-porphyrin intermediate and an Fe-III-porphyrin pi-cation radical intermediate., WILEY-BLACKWELL
CHEMISTRY-A EUROPEAN JOURNAL, 2009, [Reviewed] - Torquoselective olefination of carbonyl compounds with ynolates: Highly efficient stereoselective synthesis of tetrasubstituted alkenes
Mitsuru Shindo; Seiji Mori, The torquoselectivity-controlled olefination of carbonyl compounds with ynolates affording tetrasubstituted alkenes is described. The E/Z selectivity is determined in the step consisting of electrocyclic ring opening of the P-lactone enolates (oxetenes) derived from cycloaddition of ynolates with carbonyl compounds. Theoretical calculations revealed that several secondary orbital interactions are critical for the high torquoselectivity. This methodology is a novel olefination for constructing multisubstituted olefins., GEORG THIEME VERLAG KG
SYNLETT, Sep. 2008, [Reviewed] - Torquoselective olefination with ynolates
Mitsuru Shindo; Seiji Mori, We have developed the torquoselectivity-controlled olefination of carbonyl compounds with ynolates to afford tetrasubstituted alkenes. In the olefination of acylsilanes, alpha-oxy and alpha-aminoketones, and esters, the high selectivity and yield have been achieved under mild conditions. The E/Z selectivity is determined in the step of electrocyclic ring-opening of the beta-lactone enolates (oxetenes) derived from cycloaddition of ynolates with carbonyl compounds. The theoretical calculations revealed that the several secondary orbital interactions are critical for the high torquoselectivity. The E/Z selectivity can be estimated by considerations of the electronic properties of the substituents of carbonyl compounds, wherein the electron-donating substituents would be trans to the carboxylate on the olefins and the electron accepting ones cis to it. This methodology is the novel olefination constructing multisubstituted olefins., SOC SYNTHETIC ORGANIC CHEM JPN
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, Jan. 2008, [Reviewed] - Density Functional Studies on Thromboxane Biosynthesis: Mechanism and Role of the Heme-Thiolate System
Tetsuya K. Yanai; Seiji Mori, Reaction mechanisms for the isomerization of prostaglandin H-2 to thromboxane A(2), and degradation to 12-L-hydroxy-5,8,10-heptadecatrienoic acid (HHT) and malondialdehyde (MDA), catalyzed by thromboxane synthase, were investigated using the unrestricted Becke-three-parameter plus Lee-Yang-Parr (UB3LYP) density functional level theory. In addition to the reaction pathway through Fe-IV-porphyrin intermediates, a new reaction pathway through Fe-III-porphyrin pi-cation radical intermediates was found. Both reactions proceed with the homolytic cleavage of endoperoxide O-O to give an alkoxy radical. This intermediate converts into all allyl radical intermediate by a C-C homolytic cleavage, followed by the formation of thromboxane A(2) having a 6-membered ring through a one electron transfer, or the degradation into HHT and MDA. The proposed mechanism shows that an iron(III)-containing system having electron acceptor ability is essential for the 6-membered ring formation leading to thromboxane A(2). Our results suggest that the step of the endoperoxide O-O homolytic bond cleavage has the highest activation energy following the binding of prostaglandin H-2 to thromboxane synthase., WILEY-V C H VERLAG GMBH
CHEMISTRY-AN ASIAN JOURNAL, 2008, [Reviewed] - Quantum treatment of hydrogen nuclei in primary kinetic isotope effects in a thermal [1,5]-sigmatropic hydrogen (or deuterium) shift from (Z)-1,3-pentadiene
Yasuaki Itou; Seiji Mori; Taro Udagawa; Masanori Tachikawa; Takayoshi Ishimoto; Umpei Nagashima, The geometric and kinetic isotope effects (GIE and KIE) for thermal [1,5]-sigmatropic H and D shifts of (Z)-1,3-pentadiene were studied by including the direct quantum effect of the migrating H or D nucleus in the multi-component molecular orbital-Hartree-Fock (MC_MO-HF) method. Based on the results, the C-1-D bond lengths are 0.007 A shorter than the C-1-H bond lengths in both the reactant (A) and the transition states (TS), whereas other bond lengths resemble those between H and D. The ratio of the rate constant (k(H)/k(D)) of the reaction for the thermal [1,5]-H and D shifts determined using the MC_MO-HF method (8.28) is closer to the experimental value (12.2) than that determined using either the conventional restricted Hartree-Fock (4.10) or restricted Moller-Plesset second-order perturbation (3.79) methods., AMER CHEMICAL SOC
JOURNAL OF PHYSICAL CHEMISTRY A, Jan. 2007, [Reviewed] - Transition states of binap-rhodium(I)-catalyzed asymmetric hydrogenation: Theoretical studies on the origin of the enantioselectivity
Seiji Mori; Thom Vreven; Keiji Morokuma, By using the hybrid IMOMM(B3LYP:MM3) method, we examined the binap-Rh-I-catalyzed oxidative-addition and insertion steps of the asymmetric hydrogenation of the enamide 2-acetylamino-3-phenylacrylic acid. We report a path that is energetically more favorable for the major enantiomer than for the minor enantiomer. This path follows the "lock-and-key" motif and leads to the major enantiomeric product via an energetically favorable binap-dihydride-Rh-III-enamide complex. Our theoretical results are consistent with the mechanism that takes place via Rh-III dihydride formation, that is, oxidative addition of H-2 followed by enamide insertion., WILEY-V C H VERLAG GMBH
CHEMISTRY-AN ASIAN JOURNAL, Sep. 2006, [Reviewed] - Heteroatom-guided torquoselective olefination of alpha-oxy and alpha-amino ketones via ynolates
M Shindo; T Yoshikawa; Y Itou; S Mori; T Nishii; K Shishido, Y nolates were found to react with alpha-alkoxy-, alpha-siloxy-, and alpha-aryloxyketones at room temperature to afford tetrasubstituted olefins with high Z selectivity. Since the geometrical selectivity was determined in the ring opening of the P-lactone enolate intermediates, the torquoselectivity was controlled by the ethereal oxygen atoms, From experimental and theoretical studies, the high Z selectivity is induced by orbital and steric interactions rather than by chelation. In a similar manner, alpha-dialkylamino ketones provided olefins with excellent Z selectivity. These products can be easily converted into multisubstituted butenolides and gamma-butyrolactams in good yield., WILEY-V C H VERLAG GMBH
CHEMISTRY-A EUROPEAN JOURNAL, Dec. 2005, [Reviewed] - Elucidation of the mechanism of the 1,6-cuprate addition to acceptor-substituted enynes through C-13 kinetic isotope effects: Experimental and theoretical studies
S Mori; M Uerdingen; N Krause; K Morokuma, WILEY-V C H VERLAG GMBH
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, [Reviewed] - Hyperconjugative Effects in the Stereoselective Ring Opening Reactions of Oxetenoxides
Seiji Mori; * Mitsuru Shindo
Org. Lett., Oct. 2004, [Reviewed] - Mechanism of addition of organocuprates to alkynyl carbonyl compounds. A mechanistic bridge between carbocupration and conjugate addition
S Mori; E Nakamura; K Morokuma, The reaction pathway of the addition of a lithium dialkylcuprate to an alkynyl carbonyl compound was examined by the use of hybrid density functional calculations for Me(2)CuLi.LiCl and two carbonyl substrates, 3-butyn-2-one and methyl propynoate. Both substrates react in essentially the same manner to give first a 1,2-carbocupration product. This alpha-cupriocarbonyl product is thermodynamically stable in the case of methyl propynoate. On the other hand, the a-cupriocarbonyl product obtained from 3-butyn-2-one is in equilibrium with the corresponding lithium allenolate with a low activation barrier. Comparison of the calculated IR frequencies of the putative products with those of the experimentally obtained product mixture suggested that the product of the ynone reaction is a mixture of an alpha-cuprioketone and an allenolate, which may be in mobile equilibrium with each other in solution., AMER CHEMICAL SOC
ORGANOMETALLICS, Mar. 2004, [Reviewed] - Quantum chemical studies on interactions between heavy metal species and biomolecules
Seiji Mori; * Takahiro Endoh; Takayoshi Kishi
RMZ-Materials and Geoenvironment, Part 3, 2004 - Iron(III) chloride-catalyzed convenient one-pot synthesis of homoallyl benzyl ethers starting from aldehydes
T Watahiki; Y Akabane; S Mori; T Oriyama, graphic
Iron(III) chloride-catalyzed effective allylation reactions of acetals with allyltrimethylsilane proceeded smoothly in high to excellent yields. In addition, this method could be applied to the one-pot synthesis of homoallyl benzyl ethers by a combination of dibenzyl acetalization of aldehydes and consecutive allylation of dibenzyl acetals., AMER CHEMICAL SOC
ORGANIC LETTERS, Aug. 2003, [Reviewed] - Mechanistic studies on organometallic reactions with the aid of high-precision quantum chemical calculations
Seiji Mori; Eiichi Nakamura, Recent development in the use of high-precision quantum chemical calculations for the investigation of the mechanisms of synthetically important organometallic reaction is reviewed. The review is focused on the following issues that have be the subject of much discussion in the society of synthetic organic chemists for many years: (1) Nucleophilic addition to carbonyl compounds, (2) osmium-tetraoxide-catalyzed dihydroxylation, (3) organocopper reactions, and (4) Simmons-Smith cyclopropanation., Society of Synthetic Organic Chemistry
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2003, [Reviewed] - 高精度量子化学計算を用いた有機金属反応の解明
Seiji Mori; Eiichi Nakamura
J. Syn. Org. Chem. Jpn., 2003 - Density functional studies on kinetic reactivity of "higher order" Lipshutz cuprate in addition reaction to acetylene
M Yamanaka; S Mori; E Nakamura, There is a frequently used organocuprate species that was introduced by Lipshutz and possesses a molecular structure written as CuLi2R2(CN). This species was previously called "higher order cuprate", but is now considered to exist as an equilibrating mixture of various isomers of R2CuLi.LiCN and R(CN)CuLi-LiR, among which R2Cu-.Li2CN+ is known to be dominant in solution. The present studies on the kinetic reactivity of these species in the addition reaction to acetylene suggest that the minor species R(CN)CuLi.LiR may be more reactive than the major species, thereby making it equally possible that addition reaction products may arise through both the major and the minor reactive species. The reason for the high reactivity of the minor species has been ascribed to the anisotropic and multi-coordination capability of the cyanide ligand to metals; such capability is not available for a halide or alkyl anion ligand., CHEMICAL SOC JAPAN
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, Aug. 2002, [Reviewed] - The first general method for Z-selective olefination of acylsilanes via ynolate anions providing multisubstituted alkenes
M Shindo; K Matsumoto; S Mori; K Shishido, AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Jun. 2002, [Reviewed] - Kinetic reactivity of "higher order cuprates" in S(N)2 alkylation reactions
E Nakamura; M Yamanaka; N Yoshikai; S Mori, WILEY-V C H VERLAG GMBH
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, [Reviewed] - Mechanism of S(N)2 alkylation reactions of lithium organocuprate clusters with alkyl halides and epoxides. Solvent effects, BF3 effects, and trans-diaxial epoxide opening
Seiji Mori; Eiichi Nakamura; Keiji Morokuma, The B3LYP density functional studies on the mechanism of the S(N)2-substitution reaction of methyl halides and epoxides with lithium organocuprates(I), (CH3)2CuLi·LiCl and [ (CH3)2CuLi]2, revealed the energetics and the geometries of important transition states and intermediates along the reaction pathway. In the absence of solvent coordination on the copper atom, the reaction takes place in a single step through rate determining cleavage of the C -X bond (X = leaving group) involving nucleophilic participation of the CH3 - Cu bond composed of the copper 3d(z)2 orbital and carbon 2s+2p orbitals. Consideration of solvent polarity and coordination of an explicit (CH3)2O molecule to a lithium atom in the cuprate cluster lowers the activation energy to <
20 kcal/mol, which is a reasonable value for the reaction taking place below 0 °C. Solvation of the copper atom does not change much the geometry or the energy of the transition state, but modifies the pathway afterward. The origin of the 'trans-diaxial opening of cyclohexene oxide' has been ascribed to the inverted stereochemistry of the electrophilic carbon atom in the rate-determining step of the reaction. Coordination of BF3 lowers the activation energy of the nucleophilic ring opening of epoxide as much as to 9.2 kcal/mol. The origin of the acceleration of epoxide ring opening by BF3 is attributed to the cooperative activation of borane and lithium atoms on the epoxide oxygen atom., American Chemical Society
Journal of the American Chemical Society, 02 Aug. 2000, [Reviewed] - Mechanism of S(N)2 alkylation reactions of lithium organocuprate clusters with alkyl halides and epoxides. Solvent effects, BF3 effects, and trans-diaxial epoxide opening
S Mori; E Nakamura; K Morokuma, The B3LYP density functional studies on the mechanism of the S(N)2-substitution reaction of methyl halides and epoxides with lithium organocuprates(I), (CH3)(2)CuLi . LiCl and [ (CH3)(2)CuLi](2), revealed the energetics and the geometries of important transition states and intermediates along the reaction pathway, In the absence of solvent coordination on the copper atom, the reaction takes place in a single step through rate determining cleavage of the C-X bond (X = leaving group) involving nucleophilic participation of the CH3-Cu bond composed of the copper 3d(z)(2) orbital and carbon 2s+2p orbitals. Consideration of solvent polarity and coordination of an explicit (CH3)(2)O molecule to a lithium atom in the cuprate cluster lowers the activation energy to <20 kcal/mol, which is a reasonable value for the reaction taking place below 0 degrees C. Solvation of the copper atom does not change much the geometry or the energy of the transition state, but modifies the pathway afterward. The origin of the "trans-diaxial opening of cyclohexene oxide" has been ascribed to the inverted stereochemistry of the electrophilic carbon atom in the rate-determining step of the reaction, Coordination of BF3 lowers the activation energy of the nucleophilic ring opening of epoxide as much as to 9.2 kcal/mol. The origin of the acceleration of epoxide ring opening by BF3 is attributed to the cooperative activation of borane and lithium atoms on the epoxide oxygen atom., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Aug. 2000, [Reviewed] - Correlation of reactivities of organocuprate(I) and zincate(II) with d-orbital energies of ate complexes
S Mori; A Hirai; M Nakamura; E Nakamura, Kohn-Sham orbital analysis of MeCu, Me2Cu-, Me2Zn, Me3Zn- and Me4Zn2-, as well as the bent structures of Me2Cu-, has been performed with the density functional (B3LYP) method. It has been shown that the organozincates possess high-lying methyl carbon orbitals and low-lying d-orbitals, and hence are expected to behave as alkyl nucleophiles. On the other hand, the d-orbitals of the cuprate are at the same energy levels as the methyl carbon orbitals, and hence the cupretes react as metal-centered nucleophiles. The correlation between the bent geometry and the orbital energies of d-orbitals (z(2) and xz) was also found and has been related to the mechanistic difference between S(N)2 alkylation reaction and conjugate addition reaction. (C) 2000 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
TETRAHEDRON, Apr. 2000, [Reviewed] - Mechanism of SN2 Alkylation Reactions of Lithium Organocuprate Clusters with Alkyl Halides and Epoxides
Seiji Mori; E. Nakamura; * K. Morokuma*
J. Am. Chem. Soc., 2000, [Reviewed] - Complexation of Lewis Acid on Trialkylcopper(III) Species. On the Origin of BF3 Effects on Cuprate Conjugate Addition
Eiichi Nakamura; * Masahiro Yamanaka; Seiji Mori
J. Am. Chem. Soc., 2000, [Reviewed] - Wherefore art thou copper? Structures and reaction mechanisms of organocuprate clusters in organic chemistry
E Nakamura; S Mori, Organocopper reagents provide the most general synthetic tools in organic chemistry for nucleophilic delivery of hard carbanions to electrophilic carbon centers. A number of structural and mechanistic studies have been reported and led to a wide variety of mechanistic proposals, some of which might even be contradictory to others. With the recent advent of physical and theoretical methodologies, the accumulated knowledge on organocopper chemistry is being put together into a few major mechanistic principles. This review will summarize first the general structural features of organocopper compounds and the previous mechanistic arguments, and then describe the most recent mechanistic pictures obtained through high-level quantum mechanical calculations for three typical cuprate reactions, car, WILEY-V C H VERLAG GMBH
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, [Reviewed] - Correlation of coordination geometry of copper atom to reactivities of organocuprate. Molecular orbital analysis of dimethylcuprate anion
S Mori; E Nakamura, Kohn-Sham MO analysis of the bent structures of (CH3)(2)Cu- has been performed with the B3LYP hybrid density functional method, in the linear conformer of (CH3)(2)Cu-, which is the global minimum, the HOMO represents the copper s+d(z2) orbital, and the carbon s+p orbitals lie near this HOMO. These orbitals are responsible for the nucleophilic reactivities in the alkylation reaction of cuprates. Bending of the C-Cu-C angle pushes up the d(xz) orbital of the copper atom to mix it with the s+p orbitals of the carbon atom, generating a HOMO capable of interacting with the pi* orbital of acetylene and olefins. (C) 1999 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
TETRAHEDRON LETTERS, Jul. 1999, [Reviewed] - Theoretical studies on pi-complex formation of organocopper compounds with acetylene. The origin of nucleophilicity of organocuprates
S Mori; E Nakamura, Complexes between MeCu and Me2Cu- with acetylene have been examined with the aid of HF, MP2, and B3LYP methods. The structure of the MeCu/acetyrene complex was not much affected by the choice of the theoretical methods, since the effects of electron-correlation are rather small in this complex. The structure of the Me2Cu-/acetylene complex on the other hand, depends strongly on the method, since electron correlation plays the key role in back donation from the copper 3d(xz) orbital to the acetylene pi* orbital. As a result, the B3LYP and the MP2 methods, which take electron correlation effects into account, afforded a cupriocyclopropene pi-complex as observed experimentally, while the HF method predicted an electrostatic complex between Me2Cu- and the acidic acetylenic proton. Molecular orbital analysis indicated that the high nucleophilicity of organocuprates such as Me2Cu- is due to the back donation from the copper 3d(xz) orbital, which necessitates the use of a theoretical method that appropriately evaluates the electron correlation effects. Similarly, a d-pi* Me2Au-/acetylene complex was also located by the B3LYP calculations. (C) 1999 Elsevier Science B.V. All rights reserved., ELSEVIER SCIENCE BV
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, Apr. 1999, [Reviewed], [Invited] - Density Functional Studies on Conjugate Addition of (Me2CuLi)2 to Cyclohexenone. Diastereoselectivity and Rate Limiting Step.
Seiji Mori; Eiichi Nakamura*
Chem. Eur. J., 1999, [Reviewed] - Olefin carbometalation with (alkoxy)allylic lithium and zinc reagents. Four-centered vs six-centered mechanism of allylmetalation reaction
K Kubota; S Mori; M Nakamura; E Nakamura, Addition of substituted (alkoxy)allyllithium and zinc reagents to cyclopropenone acetal takes place smoothly to give carbometalation products of well-defined regio- and stereochemistry. The pathways of product formation depends on the metal. The (alkoxy)allylzinc reagents add to the cyclopropene in such a manner that the alpha-carbon attached to the alkoxy group becomes bound to the olefin. The regioselectivity of the (alkoxy)-allylzincation is independent of the allyl substituents, the diastereoselectivity for the newly formed carbon-carbon bond is excellent (> 97%), and the geometry of the olefinic bond in the product was always exclusively cis (if applicable). On the other hand, the regioselectivity of the (alkoxy)-allyllithiation is dependent on the substituent, while the diastereoselectivity remains constantly high (>97%). Theoretical studies supported this conjecture by revealing that a(hydroxy)allyllithium species of pi-allylmetal nature can react with cyclopropene via two [2 + 2]-type four-centered transition states of similar energies leading alpha- and gamma-adducts, while the zinc species of sigma-allylmetal nature reacts via a single [2 + 4]-type six-centered transition state leading to an alpha-adduct., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Dec. 1998, [Reviewed] - Theoretical studies on S(N)2-reaction of MeBr with Me2CuLi center dot LiCl. Solvent and cluster effects on oxidative addition/reductive elimination pathway
E Nakamura; S Mori; K Morokuma, AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Aug. 1998, [Reviewed] - S(N)2 substitution on sp(2) nitrogen of protonated oxime
S Mori; K Uchiyama; Y Hayashi; K Narasaka; E Nakamura, Theoretical studies on intramolecular nucleophilic displacement of the protonated oxime oxygen with an aryl ring revealed that the substitution reaction on the sp(2) nitrogen atom is a low energy process. This seemingly anomalous substitution is due to the low-lying sigma*-orbital of the O-protonated oxime. The theoretical conclusion received experimental support., CHEMICAL SOC JAPAN
CHEMISTRY LETTERS, 1998, [Reviewed] - Endohedral homoconjugation in cyclopentadiene embedded in C60. Theoretical and electrochemical evidence
H Iikura; S Mori; M Sawamura; E Nakamura, AMER CHEMICAL SOC
JOURNAL OF ORGANIC CHEMISTRY, Nov. 1997, [Reviewed] - Theoretical studies on the addition of polymetallic lithium organocuprate clusters to acetylene. Cooperative effects of metals in a trap-and-bite reaction pathway
Eiichi Nakamura; Seiji Mori; Masaharu Nakamura; Keiji Morokuma, Ab initio and density functional theoretical investigations into the nature of the reaction of acetylene with noncluster organocuprate reagents, MeCu, Me2Cu-, and lithium organocuprate cluster reagents, Me2CuLi, Me2-CuLi·LiCl, and (Me2CuLi)2 were carried out, and the function of the mixed metal cluster was probed. Intermediates transition structures (TSs) as well as the structures on the intrinsic reaction coordinate in the C-C bond forming stage of the reaction of lithium cuprate clusters have been calculated with the ab initio method (MP2) and density functional method (B3LYP) using all-electron basis sets for copper. The addition reaction of the simple organocopper reagent, MeCu, can be viewed as a simple four-centered addition reaction consisting of nucleophilic addition of an anionic methyl group, while the addition of the cuprate reagent, Me2Cu-, involves transfer of negative charge to the acetylene via the copper atom. In the cluster reaction of Me2CuLi·LiC1, the lithium atom in the cluster stabilizes the developing negative charge on the acetylene moiety and assists the electron flow from the copper atom. Reductive elimination of the transient Cu(III) species initially gives a 1- propenyllithuim-like structure intermediate (nonstationary point), which then undergoes intramolecular transmetalation to give the final product. 1-propenylcopper. Essentially the same mechanism operates also with Me2CuLi and (Me2CuLi)2, indicating that the Li-Me-Cu-Me moiety incorporated in the mixed organocuprate cluster is essential for the reaction. Experiments showed that the strong solvation of the lithium atom with a crown ether, which sequesters the lithium cation from the cluster, strongly decelerates the carbocupration reaction. Thus, theory and experiments revealed the cooperative function of lithium and copper atoms in the cuprate reactions.
Journal of the American Chemical Society, 28 May 1997, [Reviewed] - Reaction pathway of the conjugate addition of lithium organocuprate clusters to acrolein
E Nakamura; S Mori; K Morokuma, The reaction pathway of transfer of a methyl group of a cuprate cluster (Me2CuLi)(2) to acrolein (conjugate addition of the methyl group) has been studied with the hybrid density functional B3LYP method. All intermediates and transition structures (TSs) on the potential surface of the reaction as well as the structures on the intrinsic reaction coordinate near the C-C bond forming stage of the reaction have been determined. In addition to two previously proposed species, a lithium/carbonyl coordination complex (CPli) and a copper/olefin complex retaining a closed cuprate structure (CPcl), a new copper/olefin complex with an open cuprate structure (CPop) was characterized and proven to be an intermediate directly leading to the conjugate addition product (PD) via a TS of C-C bond formation (TS). The overall pathway of the reaction can be viewed, in one way, as C-C bond formation via reductive elimination of a Cu(III) species and, in another, as a 1,4-addition of MeLi assisted by copper. The present studies revealed that the large cluster framework of (Me2CuLi)(2) allows intricate cooperation of two lithium atoms and a copper atom. A small cluster such as Me2CuLi cannot achieve such cooperative action of different metal atoms as smoothly as larger clusters such as (Me2CuLi)(2) and Me2CuLi . LiCl. Mechanistic relationships between conjugate addition, carbocupration, and alkylation reactions of cuprate are discussed. A close similarity has been found between the conjugate addition and the carbocupration of acetylene for the cooperative action of metal and the involvement of a Cu(III) species., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, May 1997, [Reviewed] - Unusually stable organomercury hydrides and radicals
E Nakamura; Y Yu; S Mori; S Yamago, WILEY-V C H VERLAG GMBH
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, Mar. 1997, [Reviewed] - Fullerene that binds a metal on the pentagon
E Nakamura; M Sawamura; W Iikura; S Mori, ELECTROCHEMICAL SOCIETY INC
PROCEEDINGS OF THE SYMPOSIUM ON RECENT ADVANCES IN THE CHEMISTRY AND PHYSICS OF FULLERENES AND RELATED MATERIALS, VOL 4, 1997 - Open dimer participation in chelation controlled addition of methyllithium dimer to alpha- and beta-alkoxy aldehydes
S Mori; BH Kim; M Nakamura; E Nakamura, The chelation controlled additions of a MeLi dimer to alkoxy carbonyl compounds occur through an open dimer cluster, in which only one lithium atom participates in the chelate formation and the other acts as an anchor of the methyl nucleophile to be delivered to the carbonyl group. Solvation of a lithium atom with a water molecule does not change much the structure of the transition state., CHEMICAL SOC JAPAN
CHEMISTRY LETTERS, 1997, [Reviewed] - THEORETICAL-STUDIES ON CHELATION-CONTROLLED CARBONYL ADDITION - ME(2)MG ADDITION TO ALPHA-ALKOXY AND BETA-ALKOXY KETONES AND ALDEHYDES
S MORI; M NAKAMURA; E NAKAMURA; N KOGA; K MOROKUMA, The ab initio theoretical calculations on the C-C bond forming stage of the addition of Me(2)Mg to alpha- and beta-alkoxy carbonyl compounds (methoxyacetone, methoxyacetaldehyde, 3-methoxy-2-butanone, 2-methoxypropanal, 4-methoxy-2-butanone, 3-methoxypropanal, and 3-methoxybutanal) were carried out to investigate the reaction mechanism of chelation-controlled carbonyl addition reactions, for which experimental information is scarce. The carbonyl substrate and Me(2)Mg first form a stable chelate complex with 220 kcal/mol exothermicity, which undergoes C-C bond formation via 1,3-migration of the nucleophilic methyl group to the carbonyl carbon with a 6-9 kcal/mol activation energy and then gives rise to a product chelate. Chelate structure was retained throughout the reaction process. The experimental stereoselectivity of the alpha- and beta-chelation-controlled addition has been adequately reproduced. It was found for the first time that the beta-chelation-controlled reaction may proceed via either a stereoselective chair or nonselective boat transition state, the latter being energetically more favored than the former in the present system. The calculations suggested that the C-C bond forming stage is a stereochemistry determining stage as has previously been assumed., AMER CHEMICAL SOC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, May 1995, [Reviewed]
MISC
- Unusual Reactions Catalyzed by Cytochrome P450: Computational Studies on lsomerizations of Prostaglandin H(2)
Mori Seiji; Yanai K. Tetsuya
16TH INTERNATIONAL CONFERENCE ON CYTOCHROME P450, PROCEEDINGS, 2009 - Complexation of Lewis acid with trialkylcopper(III): On the origin of BF3-aceeleration of cuprate conjugate addition [13]
Eiichi Nakamura; Masahiro Yamanaka; Seiji Mori
Journal of the American Chemical Society, 01 Mar. 2000 - (Z)‐1,3‐Pentadieneの熱的[1,5]‐水素転移反応における水素同位体効果に関する理論的研究
伊藤康昭; 森聖治; 宇田川太郎; 立川仁典; 石元孝佳; 長嶋雲兵
有機反応化学討論会研究発表・講演予稿集
Books and other publications
- 計算化学 第３版
後藤仁志 (監修); 後藤仁志 (訳); 立川仁典 (監修); 立川仁典 (訳); 長嶋雲兵 (監修); 長嶋雲兵 (訳); 五十幡康弘 (訳); 内田希 (訳); 神谷 浩二 (訳); 北 幸海 (訳); 小林 正人 (訳); 佐藤 啓文 (訳); 重田 育照 (訳); 砂賀 彩光 (訳); 武次 徹也 (訳); 常田 貴夫 (訳); 長谷川 淳也 (訳); 波田 雅彦 (訳); 森 聖治 (訳), Joint translation, フランク・ジェンセン
森北出版, 31 Mar. 2023, [Reviewed]
9784627242333 - Advances in Medicine and Biology, Volume 15
T.K.Yanai; S.Mori, Joint work
Nova Science Publishers, Jul. 2011
9781611224672 - 量子物理化学入門
寺阪利孝; 森 聖治, Joint work
三共出版, 2007 - 有機化学概説
Paula Y; Bruice著; 大船; 香月,西郷; 富岡監訳, Joint translation
化学同人, Sep. 2006 - ブルース有機化学（上）第4版
Joint translation
化学同人, Oct. 2004 - 第５版 実験化学講座,「計算化学」
森 聖治; 中村栄一, Joint work
丸善, 2004 - Modern organocopper Chemistry(N. Krause, Ed.)
Seiji Mori; Eiichi Nakamura, Joint work
Wiley-VCH, 2002 - 有機量子化学（藤本博編，共著）
森 聖治; 中村栄一, Joint work
朝倉書店, 2001
Lectures, oral presentations, etc.
- Introduction to Quantum Beam Science and Computational Studies on Enzymatic and Homogeneous Catalysis
Seiji Mori
SMARTMAT 2024, 07 Nov. 2024, [Invited]
20241105, 20241108 - Introduction to Quantum Beam Science and Quantum Chemical Studies on homogeneous catalysis
Seiji Mori
International Symposium on Science and Education, 06 Jun. 2024, [Invited]
20240606, 20240606 - Molybdenum−germanium triple−bonded complex as catalyst for hydroboration of carbonyl substrates
C. Fontanilla; K. Nagata; Y. Shimizu; S. Mori; H. Hashimoto
The 9th Asian Silicon Symposium, 16 May 2024
20240512, 20240517 - 〔Major achievements〕Importance of noncovalent interactions in homogeneous and enzymatic catalysis
Seiji Mori
PACCON2024, 27 Jan. 2024, [Invited]
20240126, 20240127 - モリブデン-ゲルミリン錯体によるカルボニル化合物のヒドロホウ素化反応の理論的研究
清水 雄仁; Christof Israel Marbella Fontanilla; 長田浩一; 橋本 久子; 森 聖治
日本化学会第103春季年会(2023), 22 Mar. 2023
20230322, 20230325 - ビリン還元酵素PcyA-ビリベルジンⅨα複合体の計算科学的研究
萬代充裕; 飯島愛璃; 圷優佳; 海野昌喜; 城塚達也; 森聖治
スーパーコンピュータワークショップ2022, 17 Jan. 2023, 自然科学研究機構 岡崎共通研究施設 計算科学研究センター
20230116, 20230117 - ニッケル触媒による脱カルボニル化を含む塩化アシルのシアノ化反応に関する理論的研究
穂積 玲於; 川島 恭平; 西原 康師; 森 聖治
錯体化学会第72回討論会, 26 Sep. 2022
20220926, 20220928 - パラジウム触媒による[3+2]環化付加反応を含むベンジル及びメタ炭素-水素結合活性化反応に関する理論的研究
吉元 理江、Attila Taborosi、Qiyuan He、阿野 勇介、茶谷 直人、森 聖治
錯体化学会第72回討論会, 26 Sep. 2022
20220926, 20220928 - 〔Major achievements〕Combined DFT and experimental studies on the importance of noncovalent interactions in vanadium-catalyzed oxidative trifluoromethylation reactions of olefins
Seiji Mori and Chien-Tien Chen
WATOC 2020, 05 Jul. 2022, [Invited]
20220703, 20220708 - Theoretical Investigations of Palladium-Catalyzed Cross-Coupling of Alkenyl Carboxylates
岡本 優悟; 森 聖治
日本コンピュータ化学会2021秋季年会, 02 Nov. 2021, 日本コンピュータ化学会
20211102, 20211103 - 〔Major achievements〕Computational Perspectives of Non-covalent Interactions in Transition Metal- and Enzyme-catalyzed Reactions
Seiji Mori
錯体化学会第７1回討論会, 16 Sep. 2021, 錯体化学会, [Invited]
20210916, 20210919 - バナジウム触媒によるオレフィンの1,2-酸化的トリフルオロメチル化反応における実験的・理論的研究
藤井 稜馬・川島 恭平・森 聖治・Su Yu-Cheng・Lu Chia-Hao・Lien Chien-I・Sagar Ramu・Chen Chien-Tien
第10回CSJ化学フェスタ2020, 22 Oct. 2020, 日本化学会
20201020, 20201022 - Computational Insights into Structures and Reactions of Homogeneous and Enzymatic Catalysts
Seiji Mori
The Organic & Biomolecular Chemistry conference co-organised by The Royal Australian Chemical Institute (RACI), Royal Melbourne Institute of Technology (RMIT) and the National Organic Symposium Trust (NOST), 07 Nov. 2019, [Invited]
20191106, 20191108 - 〔Major achievements〕Bridges between experiment and theory on catalytic functions
Seiji Mori
31st IUPAP Conference on Computational Physics (CCP2019), 01 Aug. 2019, [Invited]
20190728, 20190801 - Mechanistic Insights into Metal-Catalyzed Highly Selective Homogeneous Organic Transformation Reactions
Seiji Mori
The 10th International Conference of the Asian Consortium on Computational Materials Science (ACCMS-10), 23 Jul. 2019, [Invited]
20190722, 20190726 - Bridges between Experiment and Theory on Catalytic functions
Seiji Mori
23rd International Annual Symposium on Computational Science and Engineering (ANSCSE23), 27 Jun. 2019, [Invited]
20190627, 20190629 - Bridges Between Experiment And Theory On Catalytic Functions
Seiji Mori
Computer Aided Drug Design (CADD) 2018 Seminar and Workshop, 28 Nov. 2018, [Invited]
20181128, 20181130 - Mechanistic Insights into MetalCatalyzed Highly Selective Organic Transformation Reactions
Seiji Mori
22nd International Annual Symposium on Computational Science and Engineering, 02 Aug. 2018, [Invited]
20180802, 20180804 - Mechanistic Insights into Metal-Catalyzed Highly Selective Organic Transformation Reactions
Seiji Mori
The 28th Canadian Symposium on Theoretical and Computational Chemistry (CSTCC 2018), 15 Jul. 2018, [Invited]
20180725, 20180729 - Mechanistic Insights Into Transition Metal-Catalyzed Molecular Activation Reactions
Seiji Mori
8th Asia-Pacific Conference of Theoretical and Computational Chemistry (APCTCC-8), 15 Dec. 2017, [Invited]
20171215, 20171217 - Graph theory approach in exploration of reaction path networks: Rh(I)BINAP-catalyzed isomerization of allylic amine
Takayoshi Yoshimura; Satoshi Maeda; Tetsuya Taketsugu; Masaya Sawamura; Keiji Morokuma; Seiji Mori
11th Triennial Congress of the World Association of Theoretical and Computational Chemists (WATOC), 28 Aug. 2017
20170827, 20170901 - Computational Studies of Biosyntheses of Prostaglandins and Related Signaling Compounds
Seiji Mori
6th Georgian Bay International Conference on Bioinorganic Chemistry (CANBIC-6), 23 May 2017, [Invited]
20170523, 20170527 - Mechanistic Insights into Molecular Activation Reactions Based on Computational Chemistry
Seiji Mori
10th International Conference on Computational Physics (ICCP10), 16 Jan. 2017, [Invited]
20170116, 20170120 - Theoretical Insights into Molecular Activation Reactions
Seiji Mori
Thai-Japan Symposium in Chemistry, 15 Nov. 2016, [Invited]
20161115, 20161115 - Theoretical Study on Ni(0)-Catalyzed Cross-Coupling of Methoxyarenes with Arylboronic Esters via C-O Bond Activation
20.Seiji Mori; Ryosuke Konno; Martin C. Schwarzer; H. Takahashi; Mamoru Tobisu; Naoto Chatani
10th congress on Electronic Structure: Principles and Applications (ESPA2016), 28 Jun. 2016 - Introduction of Quantum Beam Science and Applications to Chemistry and Related Sciences
Seiji Mori
8th International Kasetsart University Science and Technology Annual Research Symposium (i-KUStars), 02 Jun. 2016, [Invited] - Theoretical Studies of Molecular Activation Reactions-Mechanistic Insights and Rational Design of Catalysis-
Seiji Mori
APCTCC7, 25 Jan. 2016, APCTCC7, [Invited] - Theoretical Studies of Molecular Activation Reactions -Mechanistic Insights and Rational Design of Catalysis-
Seiji Mori
List of Participants for Molecular Design for Advanced Material : Workshop and Conference 2015, 24 Nov. 2015, [Invited] - Theoretical Studies of Molecular Activation Reactions,-Mechanistic Insights and Rational Design of Catalysis-
Seiji Mori
List of Participants for Molecular Design for Advanced Material : Workshop and Conference 2015, 24 Nov. 2015, [Invited] - Computational Studies on Mechanistic Insights Into Prostaglandin Synthases
Seiji Mori
ICoBio 2015, 05 Aug. 2015, [Invited] - Computational studies on complex mechanisms of organic and biological reactions
Theoretical Chemistry on Functional Biomolecular Systems, 10 Feb. 2015, [Invited] - Theoretical Studies of Molecular Activation Reactions -Mechanistic Insights and Rational Design of Catalysis-
Seiji Mori
The Second International Workshop on Computational Science and Engineering (IWCSE), 14 Dec. 2014, [Invited] - Computational Studies of Mechanistic Insight into Synthases of Prostaglandins and Related Signaling Compounds
Seiji Mori
Vietnam Malaysian International Chemical Congress, 07 Nov. 2014, [Invited] - Theoretical studies on biosynthesis of prostaglandin G2 by cyclooxygenase-2
Seiji Mori
ANSCSE 18, 17 Mar. 2014, [Invited] - Computational studies on C-C and C-H bond activation reactions in organic and biological chemistry
Seiji Mori
2013 WFTCPC, 09 Dec. 2013, [Invited] - Quantum Chemical and Experimental Studies on Copper-catalyzed Enantioselective Direct Alkynylation of Aldehydes with Terminal Alkynes
Seiji Mori; R. Watanabe; T.Ishii; T. Moriya; H. Ohmiya; M. Sawamura
APCTCC-6, 10 Jul. 2013, [Invited] - Computational studies on mechanistic insight into prostaglandin synthases
Seiji Mori
Pure and Applied Chemistry International Conference 2013, 23 Jan. 2013, Chemical Society of Thailand, [Invited] - Computational Studies of Mechanistic Insight into Prostaglandin Synthases
Seiji Mori; Takayuki Houjou; Ryo Watanabe; Tetsuya K. Yanai
TACC 2012, 02 Sep. 2012 - 分子動力学的手法を用いたプロスタサイクリン合成酵素と基質の複合体に関する研究
渡部 良; 吉村 誠慶; 北條 貴之; 森 聖治
第5回分子科学討論会2011札幌, 21 Sep. 2011 - Computational Studies on Complex Organic/Biological Reaction Mechanisms
Seiji Mori
14th Asian Chemical Congress, 05 Sep. 2011, [Invited] - AMBER force field parameterization of model iron-porphyrin complexes with density functional methods
Takayoshi Yoshimura; Seiji Mori
14th Asian Chemical Congress, 05 Sep. 2011 - Theoretical analysis for structures and reaction mechanisms of atypical cytochrome P450
Seiji Mori
第４８回日本生物物理学会, 21 Sep. 2010, 日本生物物理学会, [Invited] - 鉄(III)ポルフィリン錯体とエンドペルオキシドとの反応に関する理論的研究
落合 純; 野内 哲也; 岡村 賢太; 鈴木 潤; 樋口 恒彦
第４回分子科学討論会2010大阪, 15 Sep. 2010 - シトクロムP450 によるプロスタグランジンH2 の異性化反応に関する理論的研究
森 聖治; 渡部 良; 野内哲也
日本化学会 第4 回関東支部大会, 31 Aug. 2010, 日本化学会 - Computational Studies on Unusual Mechanisms of Reactions of Prostaglandin H2 Catalyzed by Cytochrome P450
Seiji Mori; Tetsuya K. Yanai; Ryo Watanabe
Sixth international conference on porphyrins and phthalocyanines (ICPP-6), 06 Jul. 2010, Society of Porphyrins and Phthalocyanines (SPP) - Theoretical Studies on Endoperoxide O-O Bond Cleavage Catalyzed by Iron Porphyrin Complexes
Seiji Mori; Jun Ochiai; Tetsuya K. Yanai; Tsunehiko Higuchi
14th International conference on biological inorganic chemistry (ICBIC 14), 27 Jul. 2009 - Important insight into Reaction Mechanisms of Organic Syntheses and Biosyntheses from View of Computational Chemistry
Seiji Mori
The International Symposium on Theory of Molecular Structure, Function and Reactivity ,Celebrating Prof. Morokuma's 75th birthday, 20 Jul. 2009, [Invited] - Unusual Reactions Catalyzed by Cytochrome P450: Density Functional Studies on Prostaglandin H2 Isomerizations
Seiji Mori; Tetsuya K. Yanai
16th International Conference on Cytochrome P450, 22 Jun. 2009 - Unusual Reactions Catalyzed by Cytochrome P450: Density Functional Studies on Prostaglandin H2 Isomerizations
Tetsuya K. Yanai; Seiji Mori
4th Asian Biological Inorganic Chemistry Conference, 10 Nov. 2008 - シクロペンタジエンの1,5-水素転移反応における速度同位体効果に関する理論的研究
内記 達哉; 伊藤 康昭; 宇田川 太郎; 立川 仁典; 石元 孝佳; 長嶋 雲兵; 森 聖治
第２回分子科学討論会, 24 Sep. 2008 - 鉄化合物に対する密度汎関数法の信頼性に関する研究
野内 哲也; 落合 純; 森 聖治
第２回分子科学討論会, 24 Sep. 2008 - シトクロムP450 によるプロスタサイクリン生合成のモデル反応機構に関する理論的研究
森 聖治; 野内 哲也
第５８回錯体化学討論会, 20 Sep. 2008 - Density functional studies on model isomerization reactions of prostaglandin H2 catalyzed by cytochrome P450
Seiji Mori; Tetsuya K. Yanai
International Symposium on Molecular Theory for Real Systems, 04 Aug. 2008 - Theoretical and UV Resonance Raman Spectroscopic Studies on Prostaglandin D2 Synthase: A Role of Glutathione and Active Site Structures in the Reaction Mechanisms.
Naoto Yamaguchi; Tatsuya Naiki; Yoshiko Uchida; Takamitsu Kohzuma; Toshikazu Takada; Fumihiko Sakata; Yoshihiro Urade; Seiji Mori
International Symposium on Molecular Theory for Real Systems, 04 Aug. 2008 - イノラートによるケトンの高立体選択的オレフィン化反応 －α位置換基の立体電子効果による回転選択性の制御
吉川 孝; 伊藤康昭; 森 聖治; 新藤 充
第6回次世代を担う有機化学シンポジウム, 30 May 2008 - 12族金属イオンとシステインの相互作用における水和の影響に関する理論的研究
矢口友貴; 熊谷衣莉; 遠藤崇浩; 野内哲也; 森 聖治
日本化学会第88春季年会, Mar. 2008 - Theoretical Studies on Model Reaction Mechanisms of Prostanoid Synthases
Seiji Mori; Tetsuya Yanai; Naoto Yamaguchi; Takamitsu Kohzuma; Toshikazu Takada; and Fumihiko Sakata
Third Asian-Pacific Conference of Theoretical and Computational Chemistry, 22 Sep. 2007 - プロスタグランジンD2/E2合成酵素反応機構のモデル系に関する理論的研究
山口 直人; 森 聖治; 高妻 孝光; 高田 俊和; 坂田 文彦
分子科学討論会2007, 18 Sep. 2007, 分子科学会 - (Z)-1,3-Pentadieneの熱的[1,5]-水素転移反応における水素同位体効果に関する理論的研究
伊藤康昭; 森 聖治; 宇田川太郎; 立川仁典; 石元孝佳; 長嶋雲兵
有機反応化学討論会, Sep. 2007 - シトクロムP450モデルによる、トロンボキサン生合成反応機構の理論的研究
野内哲也; 森 聖治
第５７回錯体化学討論会, Nov. 2006 - Theoretical studies on metal-mediated organic reactions in industry and biochemistry
Seiji Mori
Japan-China Crossover Science Workshop (Bio-chemical-physics), 15 Oct. 2006, Ibaraki University, [Invited] - Quantum Mechanical Studies on the Role of Metals in Chemistry
Seiji Mori
Japan-China Crossover Science Workshop (Bio-chemical-physics), 26 Feb. 2005, Ibaraki University, [Invited] - Resonance Between Computational Quantum Chemistry and Metal Chemistry
Seiji Mori
19th Philippine Chemistry Congress, May 2004, Philippines Chemical Society, [Invited] - Theoretical Exploration of Copper-Mediated Reaction Mechanisms. Not Only Directed to Organic Syntheses but also to Environmental Chemistry
Seiji Mori
International Symposium on Modern Organocopper Chemistry (plenary lecture), Oct. 2002, University of Dortmund, [Invited] - 有機銅化学の新展開
森 聖治
第16回若い世代の特別講演会、日本化学会第80秋季年会, Sep. 2001, 日本化学会, [Invited]
Affiliated academic society
Research Themes
- Fluorescence detection of hydrogen-bonding strength using ESIPT-type fluorescent probe
Grant-in-Aid for Scientific Research (C)
一般財団法人総合科学研究機構(総合科学研究センター(総合科学研究室)及び中性子科学センター(研究開発
01 Apr. 2021 - 31 Mar. 2024 - Mechanistic Insights into metal- and enzyme-catalyzed reactions using hybrid quantum chemical and information science approaches
Grant-in-Aid for Scientific Research (C)
Ibaraki University
01 Apr. 2021 - 31 Mar. 2024 - Development of Next-Generation Transformation Involving Molecular Activation as a Key Step
Grant-in-Aid for Specially Promoted Research
Osaka University
25 Apr. 2017 - 31 Mar. 2022 - 位置選択的天然物生合成反応メカニズムにおける酵素の役割に関する理論的研究
基盤研究(C)（一般）
Apr. 2018 - Mar. 2020 - Elucidation of Reaction Mechanism of Bili Reductase by Multiple Methods Mainly Neutron Structure Analysis
Grant-in-Aid for Scientific Research (C)
Ibaraki University
01 Apr. 2016 - 31 Mar. 2019 - 高難度高選択的物質変換反応の理論的設計
新学術領域研究
Apr. 2016 - Mar. 2018 - プロスタグランジン合成酵素の機能と反応に関する計算科学的解明
Grant-in-Aid for Scientific Research(C)
Apr. 2015 - Mar. 2018 - 量子シミュレーションに基づく不斉C–H活性化触媒の開発
JST ACT-C（先導的物質変換領域）
Oct. 2012 - Mar. 2018 - 多元素が関わる酵素反応機構の計算化学的解明
Grant-in-Aid for Scientific Research on Priority Areas
Apr. 2015 - Mar. 2017 - 量子化学計算に基づく分子活性化の活性種および反応機構の解明
Grant-in-Aid for Scientific Research on Priority Areas
Apr. 2013 - Mar. 2015 - 金属触媒による不活性結合開裂に関する理論的研究
Apr. 2011 - Mar. 2013 - Theoretical Studies on Mechanisms of Prostanoid Biosyntheses
Grant-in-Aid for Scientific Research (C)
Ibaraki University
2007 - 2009
Social Contribution Activities
Academic Contribution Activities
- 〔Major achievements〕7th International Symposium of Quantum Beam Science at Ibaraki University
Planning etc
茨城大学・量子線科学専攻長・森 聖治（組織実行委員長）, 茨城大学水戸キャンパス・ハイブリッド, 02 Dec. 2022 - 04 Dec. 2022 - The Fourth Asian Workshop of Experiment and Theory in Quantum Beam Molecular Sciences
Planning etc
茨城大学大学院理工学研究科・量子線科学専攻・森 聖治, Online, 28 Oct. 2021 - 12 Nov. 2021
