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2004 Fiscal Year Final Research Report Summary

Research of Plastic-like crystalline phases and thermal properties of urea and thiourea derivatives with long chain alkyl groups

Research Project

Project/Area Number 15550119
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionKobe University

Principal Investigator

YAMAMURA Kimiaki  Kobe University, Faculty of Science, Professor, 理学部, 教授 (60031358)

Co-Investigator(Kenkyū-buntansha) EDA Kazuo  Kobe University, Faculty of Science, Assistant, 理学部, 助手 (00193996)
Project Period (FY) 2003 – 2004
KeywordsPlastic-like phase / alkylurea / alkylthiourea / crystal structure / hydrogen bond / supramolecule / thermal analysis / catenane
Research Abstract

For such compounds as n-butylurea, n-octylurea, symmetric N, N-dibutylurea and dodecylthiourea, plastic-like crystalline phases were found by thermal analyses (DSC). In these cases, the entropy jump of the transition from normal to plastic-like phases amounts to 1/3 1/2 of that of fusion. Single crystal X-ray study elucidated the disorder of alkyl groups in the plastic-like phases and their dynamic nature were studied by solid state NMR methods.
Phase transitions were often detected for n-alkylureas. Crystal structure determinations at various temperatures revealed that the mechanism of these transitions was one or two-directional mutual slip of two-dimensional supramolecules constructed by N-H O hydrogen bonds. N-methyl, N-alkylureas with long chain alkyl groups exhibited a common phase transition in the vicinity of melting point. The mechanism of this transition would be similar to that of the n-alkylureas.
N-methyl, N-alkylthioureas with long chain alkyl groups exhibited no phase tran … More sitions in contrast to the above cases. This observation could be ascribed to the depression of the thermal motions of the alkyl groups due to a common unique interdigitation of the groups in the crystals.
Three-dimensional supramolecular assemblies with distinctive interlocking network via hydrogen bonds were seen in the crystals of 1,5-diureidopentane and 1,4-diureidobutane. DSC experiments on the compounds detected no phase transitions, but established prominent tendency of glass transitions. The crystal structure mentioned above was considered to prevent the phase transitions in the crystalline phase, but to facilitate the formation of considerably stable glassy states.
Electric conduction due to proton jump appeared to be possible in butylurea and dodecylthiourea.
Characteristics of some physical properties of such compounds as butylurea, octylurea and triptycenequinone could be controlled through modulations of local intermolecular interactions caused by formation of mixed crystal system.
Crystal structures and thermal properties were investigated for a lot of urea and thiourea derivatives. Less

  • Research Products

    (6 results)

All 2005

All Journal Article (6 results)

  • [Journal Article] Exploration of plastic-like phases in alkylurea systems. A thermal and X-ray study2005

    • Author(s)
      Masao Hashimoto
    • Journal Title

      J.Molecular Structures 734

      Pages: 23-33

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Solid solution of triptycenequinone and triptycenehydroquinone as a non-stoichiometric quinhydron. Bathochromatic changes in color caused by local intermolecular interaction between p-benzoquinone and hydroquinone moieties2005

    • Author(s)
      Kimiaki Yamamura
    • Journal Title

      J.Molecular Structures 737

      Pages: 1-6

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Three-dimensional supramolecular assembly having infinite two-dimensional interlocking networks built up only from simple and non-rigid organic molecules via hydrogen bonds. Crystal structure of α,ω-diureidoalkanes H_2N(CO)NH-(CH_2)_n-NH(CO)NH_2" with n=4 and 5.2005

    • Author(s)
      Kazuo Eda
    • Journal Title

      J.Molecular Structures 未定(in press)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Exploration of plastic-like phases in alkylurea systems. A thermal and X-ray study2005

    • Author(s)
      M.Hashimoto, F.Tajima, K.Eda, K.Yamamura, T.Okazaki
    • Journal Title

      J.Mol.Struct. 734

      Pages: 23-33

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Solid solution of triptycenequinone and triptycenehydroquinone as a non-stoichiometric quinhydron. Bathochromatic changes in color caused by local intermolecular interaction between p-benzoquinone and hydroquinone moieties2005

    • Author(s)
      K.Yamamura, T.Kawashima, K.Eda, F.Tajima, M.Hashimoto
    • Journal Title

      J.Mol.Struct. 737

      Pages: 1-6

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Three-dimensional supramolecular assembly having infinite two-dimensional interlocking networks built up only from simple and non-rigid organic molecules via hydrogen bonds. Crystal structure of α,ω-diureidoalkanes H_2N(CO)NH-(CH_2)_n-NH(CO)NH_2 with n = 4 and 52005

    • Author(s)
      K.Eda, T.Okazaki, K.Yamamura, M.Hashimoto
    • Journal Title

      J.Mol.Struct. (in press)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2006-07-11  

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