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Mechanism of formation of chiral crystals studied by using induced-chiral molecule as a probe

Research Project

Project/Area Number 16550014
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Physical chemistry
Research InstitutionOKYAMA UNIVERSITY Gvani Aid-For

Principal Investigator

ISHIDA Hiroyuki  Graduate School of Natural Science and Technology, Professor, 大学院自然科学研究科, 教授 (70193331)

Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 2006: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2005: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2004: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsCrystal Structure Analysis / Hydrogen Bond Scheme / Chiral Crsytal / X線結晶構造解析
Research Abstract

Tartornic acid, phenylmaronic acid and chloronitrobenzoic acid have been undertaken as model compounds in order to investigate the mechanism of formation of chiral crystals which are composed of achiral molecules. The acidic anions of the first two compounds are optically active. The last one has an axial-chirality when it is crystallized. We have prepared salts or intermolecular compounds of the above compounds with amine, pyridine and amino acid derivatives, and determined the crystal structures by single crystal X-ray diffraction. Furthermore, we have determined crystal structures of salts or intermolecular compounds of chloranilic acid with amine, pyridine and amino acid derivatives in order to investigate their hydrogen bond scheme and the proton transfer mechanism in the hydrogen bond.
Part of the results have already been published in the international crystallographic journals. The published crystal structures are: (1) 2-pyridone-tartronic acid (1/1), 3-hydroxypyridinium hydrogen tartronate and 4-hydroxypyridinium hydrogen tartronate; (2) benzimidazolium hydrogen phenylmalonate; (3) 3,5-lutidinium-2-chloro-4-nitrobenzoate-2-chloro-4-nitrobenzoic acid (1/1/1), 3-cyanopyridine-2-chloro-4-nitrobenzoic acid (1/1); (4) chloranilate with carboxypyridinium, cytosinium, phenazine, picolinium, piperidinium, pyrrolidinium, methylpyrazolium, tetrahydroquinolinium and trimethylpyridinium ion.

Report

(4 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (44 results)

All 2007 2006 2005 2004

All Journal Article (44 results)

  • [Journal Article] Bis(piperidinium) Chloranilate2007

    • Author(s)
      M.S.Refat, H.Al-D.Ahmed, L.A.El-Zalat, T.Fukunaga, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] N-[5-(1-Naphthyl)pyrimidin-4-yl]acetamide oxime2007

    • Author(s)
      K.Okuda, H.Watanabe, T.Hirota, H.Ishida
    • Journal Title

      Acta Cryst. E63

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Poly[(μ_4-chloranilato)bis(saccharin)disodium(I)]2007

    • Author(s)
      M.S.Refat, H.A.Hashem, K.Gotoh, H.Ishida
    • Journal Title

      Acta Cryst. E63

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Hydrogen bonding in two solid phases of phenazine-chloranilic acid (1/1) determined at 170 and 93 K2007

    • Author(s)
      K.Gotoh, T.Asaji, H.Ishida
    • Journal Title

      Acta Cryst. C63

    • NAID

      120002314091

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Trimethylammonium perchlate at 97 K2006

    • Author(s)
      T.Gotoh, R.Ishikawa, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Crystal Structure of 4'-O-methylalpinumisoflavone at 90 K2006

    • Author(s)
      R.Kingsford-Adaboh, E.Ahiano, B.Dittrich, H.Okamoto, M.Kimura, H.Ishida
    • Journal Title

      Crystal Res. Technol. 41

      Pages: 728-733

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Invariom Structure Refinement, Electrostatic Potential and Toxicity of 4-0-Methylalpinumisoflavone, O,O-Dimethylalpinumisoflavone and 5-O-Methyl-4-O-(3-methvlbut-2-en-1-yl) alninumisoflavone2006

    • Author(s)
      R.Kingsford-Adaboh, B.Dittrich, C.B.Hubschle, W.S.K.Gbewonyo, H.Okamoto, M.Kimura, H.Ishida
    • Journal Title

      Acta Cryst. B62

      Pages: 843-849

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Monoprotonated [2.2.2]Cryptand Picrate Monohydrate2006

    • Author(s)
      M.S.Refat, K.Gotoh, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 4-Carboxypyridinium hydrogen chloranilate monohydrate2006

    • Author(s)
      K.Gotoh, Y.Tabuchi, H.Akashi, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Cytosinium Hydrogen Chloranilate Monohydrate2006

    • Author(s)
      K.Gotoh, R.Ishikawa, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 2,4-Dimethoxy-6-methylbenzoic acid2006

    • Author(s)
      A.Saeed, K.Gotoh, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Hydrogen bonding in two solid phases of phenazine-chloranilic acid (1/1) determined at 170 and 93 K2006

    • Author(s)
      K.Gotoh, T.Asaji, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • NAID

      120002314091

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Bis(piperidinium) Chloranilate2006

    • Author(s)
      M.S.Refat, H.Al-D.Ahmed, L.A.El-Zalat, T.Fukunaga, H.Ishida
    • Journal Title

      Acta Cryst. E62

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Invariom Structure Refinement, Electrostatic Potential and Toxicity of 4-o-Methylalpinumisoflavone, o, o-Dimethylalpinumisoflavone and 5-o-Methyl-4-o-(3-methylbut-2-en-l-y1) alpinumisoflavone2006

    • Author(s)
      R.Kingsford-Adaboh, B.Dittrich, C.B.Hubschle, W.S.K.Gbewonyo, H.Okamoto, M.Kimura, H.Ishida
    • Journal Title

      Acta Cryst. B62

      Pages: 843-849

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Cytosiniun Hydrogen Chloranilate Monohydrate2006

    • Author(s)
      K.Gotoh, R.Ishikawa, H.Ishida
    • Journal Title

      Acta Cryst.E E62

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Bis(piperidinium)Chloranilate2006

    • Author(s)
      M.S.Refat, H.AI-D.Ahmed, L.A.EI-Zalat, T.Fukunaga, H.Ishida
    • Journal Title

      Acta Cryst.E E62

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Invariom Structure Refinement, Electrostatic Potential and Toxicity of 4-O-Methylalpinumisoflavone,O,O-Dimethylalpinumisoflavone and 5-O-Methyl-4-(3-methylbut-2-en-1-yl) alpinumisoflavone2006

    • Author(s)
      R.Kingsford-Adaboh, B.Dittrich, C.B.Hubschle, W.S.K.Gbewonyo, H.Okamoto, M.Kimura, H.Ishida
    • Journal Title

      Acta Cryst B B62

      Pages: 843-849

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Monoprotonated〔2.2.2〕Cryptand Picrate Monohydrate2006

    • Author(s)
      M.S.Refat, K.Gotoh, H.Ishida
    • Journal Title

      Acta Cryst.E E62

    • Related Report
      2006 Annual Research Report
  • [Journal Article] 4-Carboxypyridinium hydrogen chloranilate monohydrate2006

    • Author(s)
      K.Gotoh, Y.Tabuchi, H.Ishida
    • Journal Title

      Acta Cryst E E62

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Trimethylammonium Perchlate at 97 K2006

    • Author(s)
      T.Gotoh, R.Ishikawa, H.Ishida
    • Journal Title

      Acta Cryst.E E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Calorimetric and single crystal X-ray study of the phase transition of (PyH)_2PdCl_42005

    • Author(s)
      T.Asaji, H.Fujimori, H.Ishida, K.Eda, M.Hashimoto, M.Oguni
    • Journal Title

      J. Phys. Chem. Solids 66

      Pages: 869-875

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Benzimidazolium hydrogen phenylmalonate2005

    • Author(s)
      S.Ueda, T.Fukunaga, H.Ishida
    • Journal Title

      Acta Cryst. E61

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] H-Transfer Motions in an H-Bonded (Chloranilic Acid)-(1,3-Diazine) 1 : 2 Molecular Complex Studied by ^(35)Cl NQR and ^1H NMR2005

    • Author(s)
      R.Ikeda, S.Takahashi, T.Nihei, H.Ishihara, H.Ishida
    • Journal Title

      Bull. Chem. Soc. Jpn. 78

      Pages: 1241-1245

    • NAID

      10016580049

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Trimethylammonium tetrafluoroborate at 100 K2005

    • Author(s)
      T.Gotoh, R.Ishikawa, H.Ishida
    • Journal Title

      Acta Cryst. E61

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 2-Carboxypyridinium hydrogen chloranilate2005

    • Author(s)
      Y.Tabuchi, A.Takahashi, T.Gotoh, H.Akashi, H.Ishida
    • Journal Title

      Acta Cryst. E61

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] H-Transfer Motions in an H-Bonded (Chloranilic Acid)-(1,3-Diazine) 1 : 2 Molecular Complex Studied by ^<35>Cl NQR and 1^HNMR2005

    • Author(s)
      R.Ikeda, S.Takahashi, T.Nihei, H.Ishihara, H.Ishida
    • Journal Title

      Bull. Chem. Soc. Jpn. 78

      Pages: 1241-1245

    • NAID

      10016580049

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Benzimidazolium Hydrogen Phenylmalonate2005

    • Author(s)
      S.Ueda, T.Fukunaga, H.Ishida
    • Journal Title

      Acta Cryst.E E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Trimethylammonium Tetrafluoroborate at 100 K2005

    • Author(s)
      T.Gotoh, R.Ishikawa, H.Ishida
    • Journal Title

      Acta Cryst.E E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 2-Carboxypyridinium Hydrogen Chloranilate2005

    • Author(s)
      Y.Tabuchi, A.Takahashi, T.Gotoh, H.Akashi, H.Ishida
    • Journal Title

      Acta Cryst.E E61

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Pyrrolidinium chloranilate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 2-Pyridone-tatronic acid (1/1), 3-hydroxypyridinium hydrogen tartronate and 4-hydroxypyridinium hydrogen tartronate2004

    • Author(s)
      T.Fukunaga, S.Kashino, H.Ishida
    • Journal Title

      Acta Cryst. C60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 3,5-Lutidinium-2-chloro-4-nitrobenzoate-2-chloro-4-nitrobenzoic acid (1/1/1)2004

    • Author(s)
      H.Ishida, B.Rahaman, S.Kashino
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 3-Cyanopyridine-2-chloro-4-nitrobenzoic acid (1/1)2004

    • Author(s)
      H.Ishida, T.Fukunaga
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 1,2,3,4-Tetrahydroquinolinium hydrogen chloranilate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Bis(3-picolinium) chloranilate dihydrate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Bis(2,4,6-trimethylpyridinium) chloranilate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Bis(3-methylpyrazolium) chloranilate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst. E60

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 2-Pyridone-tartronic acid (1/1), 3-hydroxypyridinium hydrogen tartronate and 4-hydroxypyridinium hydrogen tartronate2004

    • Author(s)
      T.Fukunaga, S.Kashino, H.Ishida
    • Journal Title

      lActa Cryst. C60

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 2-Pyridone-Tatronic acid (1/1), 3-Hydroxypyridinium Hydrogen Tartronate and 4-Hydroxypyridinium Hydrogen Tartronate2004

    • Author(s)
      T.Fukunaga, S.Kashino, H.Ishida
    • Journal Title

      Acta Cryst.C C60

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 3,5-Lutidinium-2-Chloro-4-nitrobenzoate-2-Chloro-4-nitrobenzoic acid(1/1/1)2004

    • Author(s)
      H.Ishida, B.Rahaman, S.Kashino
    • Journal Title

      Acta Cryst.E E60

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 3-Cyanopyridine-2-Chloro-4-nitrobenzoic acid(1/1)2004

    • Author(s)
      H.Ishida, T.Fukunaga
    • Journal Title

      Acta Cryst.E E60

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 1,2,3,4-Tetrahydroquinolinium Hydrogen Chloranilate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst.E E60

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Bis(3-picolinium) chloranilate dihydrate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst.E E60

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Bis(2,4,6-trimethylpyridinium) chloranilate2004

    • Author(s)
      H.Ishida
    • Journal Title

      Acta Cryst.E E60

    • Related Report
      2004 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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