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In Search of Methodology Determineng Kinetic Isotope Effect on Organic Fundamental Reactions

Research Project

Project/Area Number 62430007
Research Category

Grant-in-Aid for General Scientific Research (A)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionKyoto University

Principal Investigator

HAYAMI Jun-ichi  Kyoto Univ., Dept. of Lip. Arts and Sci., Professor, 教養部, 教授 (30025283)

Co-Investigator(Kenkyū-buntansha) MATSUBARA Takaharu  Kyoto Univ., Dept. of Lib. Arts and Sci., Instructor, 教養部, 助手 (50026811)
MATSUMOTO Kiyoshi  Kyoto Univ., Dept. of Lib. Arts & Sci., Prof., 教養部, 教授 (20026818)
KOJIMA Shinpei  Kyoto Univ., Dept. of Lib. Arts and Sci., Prof., 教養部, 教授 (80026012)
OTANI Shin-ichi  Kyoto Univ., Dept. of Lib. Arts and Sci., Prof., 教養部, 教授 (10026768)
Project Period (FY) 1987 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥21,600,000 (Direct Cost: ¥21,600,000)
Fiscal Year 1990: ¥100,000 (Direct Cost: ¥100,000)
Fiscal Year 1989: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1988: ¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 1987: ¥15,000,000 (Direct Cost: ¥15,000,000)
KeywordsIsotope effect determination / Kie determination / Hihg resolution mass spectrometer / Whole molecule mass spectrometry / Isotopec abundance measurement / Chlorine isotope abundance measurement / 高分解能質量分析 / ホ-ルモレキュ-ル質量分析法 / 脱離基同位体効果 / 求核置換反応 / 有機基礎反応 / GCーMS / ホールモレキュール質量分析法
Research Abstract

In search of a methodology to determine the kinetic isotope effect on fundamental organic reactions in an ordinary organic chemistry laboratory, we pursued the possibility of conducting whole molecule mass spectrometry with a double-focusing high resolution mass spectrometer. For this purpose, a quadrupole mass spectrometer is generally an instrument of choice because it allows a rapid and repeated scanning of mass peaks.
In Japanese institutions, quadrupole instrument is far less popular compared to high resolution mass spectrometers and such a scarce availability seem to limit the application of this potentially useful means of isotope effect measurements.
However, recent innovations allow rapid and repeated scanning of mass peaks with a high resolution instrument, thus allowing us to be involved in an isotope effect study more easily. A JEOL JMS-DX302 mass spectrometer was utilized for this purpose and worked beautifully. Isotope peak ratio for molecular ion peaks are determined with benzyl chloride, o- and p-dichlorobenzene. On accumulating 20,000 scans, the accuracy could reach as good as 1 to 10,000 when the peak intensities are measured by a peak area. Some reservations and further improvements should be made, however, to do satisfactory whole molecule mass spectrometry. For example, an improved dynamic range of data accumulator would promise a higher accuracy, provided a better tail detection is managed.

Report

(5 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • 1988 Annual Research Report
  • 1987 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Junーichi Hayami: "Rate Controlling Role of the Aprotic Solvents in the Aromatic Nucleophilic Substitution Reaction and the Possible Intervention of a SubstrateーNucleophile Complex as an Intermediate of the Reaction" Chemistry Letters. 739-742 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Tetsuji Kawamoto: "Synthesis and Reaction of 5ーDeazaflavin with Axial and Planar Chirality" Tetrahedron Letters. 52. 7431-7434 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junーichi Hayami: "An Enantioselective Role of a Ternary Complex in the Asymmetric "Hydride" Transfer Reaction between NAD(P)H Model Compound and 5ーDeazaflavin possessing Planar Chirality" Tetrahedron Letters. (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junーichi Hayami: "Kinetic Studies of the Aromatic Nuclephilic Substitution Reaction of 2,4,6ーTrinitrofroflorobenzene and 2,4ーDimethoxyaniline in Acetoーnitrile.Evidence of Rate Controlling Solvation and Desolvation" Tetrahedron Letters. (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Jun-ichi Hayami, Shin-ichi Otani, Fumio Yamaguchi, and Yasuharu Nishikawa: ""Rate Controlling Role of the Aprotic Solvents in the Aromatic Nucleophilic Substitution Reaction and the Possible Interventions of a Substrate-Nucleophile Complex as an Intermediate of the Reaction"" Chemistry Letters. 739-742 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Tetsuji Kawamoto, Kiyoshi Tanaka, Fumio Yoneda, and Jun-ichi Hayami: ""Synthesis and Reaction of 5-Deazaflavin with Axial and Planar Chirality"" Tetrahedron Letters. No52. 7431-7434 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Jun-ichi Hayami, Tetsuji Kawamoto, Kiyoshi Tanaka, and Fumio yoneda: ""An Enantioselective Role of a Ternary Complex in the Asymmetric "Hydride" Transfer Reaction between NAD(P)H Model Compound and 5-Deazaflavin Possessing Planar Chirality"" Tetrahedron Letters. (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Jun-ichi Hayami, Kyoko Yabu, Naoto Mukaida, and Yasuharu Nishikawa: ""Kinetic Studies of the Aromatic Nucleophilic Substitution Reaction of 2, 4, 6-Trinitrofluorobenzene and 2, 4-Dimethoxyaniline in Acetonitrile. Evidence of Rate Controlling Solvation and Desolvation"" Tetrahedron Letters. (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junーichi Hayami: "Rate Controlling Role of the Aprotic Solvents in the Aromatic Nucleophilic Substitution Reaction and the Possible Intervention of a SubstrateーNucleophile Complex as an Intermediate of the Reaction" Chemistry Letters. 739-742 (1987)

    • Related Report
      1990 Annual Research Report
  • [Publications] Tetsuji Kawamoto: "Synthesis and Reaction of 5ーDeazaflavin with Axial and Planar Chirality" Tetrahedron Letters. 52. 7431-7434 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] Junーichi Hayami: "An Enantioselective Role of a Ternary Complex in the Asymmetric“Hydride"Transfer Reaction between NAD(P)H Model Compound and 5ーDeazaflavin Possessing Planar Chirality" Tetrahedron Letters. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] Junーichi Hayami: "Kinetic Studies of the Aromatic Nucleophilic Substitution Reaction of 2,4,6ーTrinitroflorobenzene and 2,4ーDimethoxyaniline in Acetonitrile.Evidence of Rate Controlling Solvation and Desolvation" Tetrahedron Letters. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] Jun-ichi Hayami,Shinーichi Otani,Fumio Yamaguchi,and Yasuharu Nishikawa.: "Rate Controlling Role of the Aprotic Solvents in the Aromatic Nucleophilic Substitution Reaction and the Possible Intervention of a Substrate-Nucleophile Complex as an Intermediate of the Reaction" Chemistry Letters. 739-742 (1987)

    • Related Report
      1989 Annual Research Report
  • [Publications] Tetsuji Kawamoto,Kiyoshi Tanaka,Fumio Yoneda,and Jun-ichi Hayami: "Synthesis and Reaction of 5-Deazaflavin with Axial and Planar Chirality" Tetrahedron Letters. 30. 7431-7434 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Jun-ichi Hayami,Tetsuji Kawamoto,Kiyoshi Tanaka,and Fumio Yoneda.: "An Enantioselective Role of a Thernary Complex in the Asymmetric“Hydride"Transfer Reaction between NAD(P)H Model Compound and 5-Deazaflavin Possessing Planar Chirality" Tetrahedron Letters. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Junーichi Hayami,Kyoko Yabu,Naoto Mukaida,and Yasuharu Nishikawa: "Kinetic Studies of the Aromatic Nucleophilic Substitution Reaction of 2,4,6-Trinitroflorobenzene and 2,4-Dimethoxyaniline in Acetonitrile.Evidence of Rate Controlling Solvation and Desolvation" Tetrahedron Letters. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] 速水醇一: Proceeding of the 1988 Kyushu Symposium.On Physical Organic Chemistry.55-58 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 速水醇一: CHEMISTRY LETTERS. 4 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 速水醇一: CHEMISTRY LETTERS. 4 (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] 速水醇一,向田直人,西川泰信: J. CHEM. SOC. CHEM. COMMUN.2 (1988)

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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