2001 Fiscal Year Final Research Report Summary
Correlation between the molecular structures and thermodynamic parameters of chiral recognition on Host-Guest complexation
| Project/Area Number |
12640518
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | OSAKA UNIVERSITY |
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Principal Investigator |
HIROSE Keiji Osaka University, Engineering Science, Chemistry, Associate Professor, 大学院・基礎工学研究科, 助教授 (10252628)
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| Project Period (FY) |
2000 – 2001
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| Keywords | Chiral Recognition / Crown Ether / Amine / Optically Active / Enthalpy / Entropy / Temperature Dependence / Criteria Of Molecular Design |
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| Research Abstract |
In the cases of many complexations of crown ethers with amines, there is a linear relationship between 1n K and 1/T, which is called the van't Hoff relationship. Based on the van't Hoff relationship, the enthalpy and the entropy can be obtained quantitatively. In addition to an ordinary adopted molecular design based on qualitative host-guest complimentarity judged by a steric hindrance and a fittability between the size of cavity and that of substrate, novel criteria based on the enthalpy and entropy were thought to be contribute to create the precise molecular design of host. Here I extended this idea to a chiral recognition phenomena. I carried out this research as following three steps.
(1) The syntheses of optically active artificial hosts and guests, which are correlated by the structural similarity.
(2) Measurements of binding constants in the complexation between series of hosts and chiral amines.
(3) Investigation of molecular recognition mechanism thinking the thermodynamic parameters.
Novel six hosts and both enantiomers of 3 chiral amines were prepared, the measurements of binding constants in the complexation between part of the host-guest combinations were carried out. And the results are published under the consideration of thermodynamic parameters.
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[Publications] Masami Sawada, Kouji Hagita, Hiroyuki Imamura, Hiroyuki Tabuchi, Shinya Yodoya, Maki Umeda, Yoshio Takai, Hitoshi Yamada, Hiroshi Yamaoka, Keiji Hirose, Yoshito Tobe, Toshikazu Tanaka, Shigetoshi Takahashi: "Chiral Recognition Ability of Crown Ethers toward Organic Amine Compounds : FAB Mass Spectrometry Coupled with the Enantiomer-Labeled Guest Method"J. Mass. Spec. Soc. Jpn.. 48. 323-332 (2000)
Description
「研究成果報告書概要(和文)」より
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[Publications] Masami Sawada, Kouji Hagita, Hiroyuki Imamura, Hiroyuki Tabuchi, Shinya Yodoya, Maki Umeda, Yoshio Takai, Hitoshi Yamada, Hiroshi Yamaoka, Keiji Hirose, Yoshito Tobe, Toshikazu Tanaka, and Shigetoshi Takahashi: "Chiral Recognition Ability of Crown Ethers toward Organic Amine Compounds : FAB Mass Spectrometry Coupled with the Enantiomer-Labeled Guest Method"J. Mass. Spec. Soc. Jpn.. 48. 323-332 (2000)
Description
「研究成果報告書概要(欧文)」より
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