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ANALYSIS OF DYNAMIC STRUCTURE WITH CHEMICAL SHIFT SIMULATION METHOD

Research Project

Project/Area Number 15350025
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

FUKAZAWA Yoshimasa  Hiroshima University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (50004502)

Co-Investigator(Kenkyū-buntansha) IWAMOTO Hajime  Hiroshima University, Graduate School of Science, Reseach Associate, 大学院・理学研究科, 助手 (80304393)
Project Period (FY) 2003 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥15,000,000 (Direct Cost: ¥15,000,000)
Fiscal Year 2005: ¥4,400,000 (Direct Cost: ¥4,400,000)
Fiscal Year 2004: ¥5,100,000 (Direct Cost: ¥5,100,000)
Fiscal Year 2003: ¥5,500,000 (Direct Cost: ¥5,500,000)
KeywordsChemical Shift Simulation / Induced Magnetic Shielding / New Chiral Auxiliary / Absolute Configuration / Porphvrin Ring Current / 環電流効果 / 科学シフト計算法 / 二級アルコール体絶対配置 / ポルフィリン環電流効果 / テトラフェニルポルフィリン / 2級アミン / ビナフチル
Research Abstract

Determination of significantly populated conformers in extremely flexible molecules is a matter of long-standing interest. It is desirable to develop an efficient method for the conformational analysis of the flexible compounds. NMR chemical shifts reflect molecular structure. Hence, variation in the local environment affects chemical shieldings, and the change in chemical shifts of nuclei caused by adjacent substituents provides valuable information about the relative arrangement of the nuclei under study with respect to these nearby substituents. The chemical shift changes caused by the nearby substituents can thus be applicable for conformational analysis. From this point of view, we have developed an efficient method for conformational analysis of flexible organic compounds by using chemical shift simulation technique. The followings are the results of the project.
(1) Magnetic shielding effects of polar functional groups were successfully estimated and were applied for the conformational analysis of the flexible compounds, including cyclophanes, molecular tweezers, and their supramolecular complexes.
(2) A very useful model of porphyrin ring current effect was developed by using a classical line current approximation. It was found that the model can successfully elucidate the structures of several dicarboxylate complexes of Sn^<(IV)> porphyrins in solution.
(3) The newly developed method for the conformational analysis by using chemical shift simulation technique was found to be highly efficient for the structure elucidation of flexible organic compounds.

Report

(4 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • Research Products

    (39 results)

All 2006 2005 2004 2003 Other

All Journal Article (34 results) Publications (5 results)

  • [Journal Article] Determination of absolute configuration of secondary alcohols using new chiral auxiliary and chemical shift calculation2006

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Letters 47・10

      Pages: 1519-1523

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Structure elucidation of dicarboxylate complex of Sn^<IV> porphyrin with a ring current effect model2006

    • Author(s)
      H.Iwamoto
    • Journal Title

      Tetrahedron 62

      Pages: 2789-2798

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Determination of absolute configuration of secondary alcohols using new chiral auxiliary and chemical shift calculation2006

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Letters 47

      Pages: 1519-1523

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Supramolecular Nano Networks Formed by Molecular-Recognition-Directed Self-Assembly of Ditopic Calix[5]arene and Dumbbell[60]Fullerene2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Journal of the American Chemical Society 127・25

      Pages: 8936-8937

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Calix[5]arene-based receptor for dumb-bell shaped C_<120>2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Bulletin of the Chemical Society of Japan 78・5

      Pages: 768-770

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Conformational analysis of dinaphthalence-1-carboxylate complex of Sn^<IV>(tetraphenylporphyrin)2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Heterocycles 65・

      Pages: 523-529

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Shielding effect of thioether C-S bond from proton chemical shifts of 4-thia-5α- and 4-thia-5β- androstane-17-ones2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron 61・15

      Pages: 3691-3696

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A model of porphyrin ring current effect2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Letters 46・5

      Pages: 731-734

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Conformational Analysis of Flexible Compounds with Chemical Shift Simulation2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      J. Synth. Org. Chem. Jpn. 63

      Pages: 1080-1089

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Supramolecular Nano Networks Formed by Molecular-Recognition-Directed Self Assembly of Ditopic Calix[5]arene and Dumbbell [60]Fullerene2005

    • Author(s)
      T.Haino
    • Journal Title

      J Am. Chem. Soc. 127

      Pages: 8936-8937

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Calix[51arene-based receptor for dumb-bell-shaped C_<120>2005

    • Author(s)
      T.Haino
    • Journal Title

      Bull. Chem. Soc. Japan 78

      Pages: 768-770

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Conformational analysis of dinaphthalene-1-carboxylate complex of Sn^<IV>(tetraphenylporphyrin)2005

    • Author(s)
      H.Iwamoto
    • Journal Title

      Heterocycles 65

      Pages: 523-529

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Shielding effect of thioether C-S bond from proton chemical shifts of 4-thia-5α- and 4-thia-5β-androstane-17-ones2005

    • Author(s)
      H.Iwamoto
    • Journal Title

      Tetrahedron 61

      Pages: 3691-3696

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Self-complementary bis-porphyrins2005

    • Author(s)
      T.Haino
    • Journal Title

      Tetrahedron 46

      Pages: 257-260

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A model of porphyrin ring current effect2005

    • Author(s)
      H.Iwamoto
    • Journal Title

      Tetrahedron 46

      Pages: 1411-1414

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Conformational control of flexible molecular tweezers by intramolecular CH/π interaction2005

    • Author(s)
      H.Iwamoto
    • Journal Title

      Tetrahedron 46

      Pages: 6839-6842

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Conformational Analysis of Flexible Compounds with Chemical Shift Simulation2005

    • Author(s)
      H.Iwamoto
    • Journal Title

      J Synth. Org. Chem. Japan 63(11)

      Pages: 1080-1089

    • NAID

      10016764921

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Supramolecular Nano Networks Formed by Molecular-Recognition-Directed Self-Assembly of Ditopic Calix[5]arene and Dumbbell[60]Fullerene2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Journal of the American Chemical Society 127

      Pages: 8936-8937

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Calix[5]arene-based receptor for dumb-bell-shaped C_1202005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Bulletin of the Chemical Society of Japan 78・5

      Pages: 768-770

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Conformational analysis of dinaphthalene-1-carboxylate complex of Sn^IV(tetraphenylporphyrin)2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Heterocycles 65

      Pages: 523-529

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Shielding effect of thioether C-S bond from proton chemical shifts of 4-thia-5α-and 4-thia-5β-androstane-17-ones2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron 61

      Pages: 3691-3696

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A model of porphyrin ring current effect2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Letters 46

      Pages: 731-734

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Model of Porphyrin Ring Current Effect2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Lett 46・5

      Pages: 731-734

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Conformational Analysis of Dinaphthalene-1-carboxylate Complex of Sn^<IV>(tetraphenylporphyrin)2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      HETEROCYCLES 65・3

      Pages: 523-530

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Shielding effect of thioether C-S bond from proton chemical shiofs of 4-thia-5α- and 4-thia-5β-androstane-17-ones2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron 61・15

      Pages: 3691-3696

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Self-complementary bis-porphyrins2005

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Letters 46・1

      Pages: 257-260

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Solid-phase synthesis of liquid crystalline isoxazole library2004

    • Author(s)
      T.Haino
    • Journal Title

      Tetrahedron Letters 45

      Pages: 2277-2279

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Calix[4]arene-based ditopic receptor for dicarboxylates2004

    • Author(s)
      T.Haino
    • Journal Title

      Tetrahedron Letters 45

      Pages: 2281-2284

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of molecular tweezers bearing two porphyrins and its complexation toward electron acceptors2004

    • Author(s)
      H.Iwamoto
    • Journal Title

      Heterocycles 63

      Pages: 2005-2011

    • NAID

      40006382278

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Solid-phase synthesis of liquid crystalline isoxazole library2004

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      Tetrahedron Letters 45・11

      Pages: 2277-2279

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of molecular tweezers bearing porphyrins and its complexation toward electron acceptors2004

    • Author(s)
      Yoshimasa Fukazawa
    • Journal Title

      HETEROCYCLES 63・9

      Pages: 2005-2011

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Convenient synthesis of [3]catenane by olefin metathesis dimerizations.2003

    • Author(s)
      H.Iwamoto
    • Journal Title

      Tetrahedron Letters 44

      Pages: 5773-5776

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Magnetic shielding effect of amine anc ammonium groups obtained from protorr chemical shifts of androstane derivatives2003

    • Author(s)
      H.Iwamoto
    • Journal Title

      Tetrahedron Letters 44

      Pages: 5975-5978

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] On-beads screening of solid-attached diketopiperazines for calix[5]arene-based receptor2003

    • Author(s)
      T.Haino
    • Journal Title

      Tetrahedron Letters 44

      Pages: 3889-3892

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Publications] Yoshimasa Fukazawa: "On-beads screenibg of solid-attached diketopiperazines for calix[5]arene-based receptor"Tetrahedron Letters. 44・20. 3889-3892 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshimasa Fukazawa: "Convenient synthesis of [3]catenen by olefin metathesis dimerization"Tetrahedron Letters. 44・31. 5773-5776 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshimasa Fukazawa: "Magnetic shielding effect of amine and ammonium groups obtained from proton chemical shifts of androstane derivatives"Tetrahedron Letters. 44・32. 5975-5978 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshimasa Fukazawa: "Solid-Phase ditopic receptor for dicarboxylates"Tetrahedron Letters. 45・11. 2277-2279 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshimasa Fukazawa: "Calix[4]arene-based ditopic receptor for dicarboxylates"Tetrahedron Letters. 45・11. 2281-2284 (2004)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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