JMSSJ On-line, Vol. 48 (2000) No. 5, pp. 323-332
Chiral Recognition Ability of Crown Ethers toward Organic Amine Compounds: FAB Mass Spectrometry Coupled with the Enantiomer-Labeled Guest Method
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    Masami SAWADA*a), Kouji HAGITAb), Hiroyuki IMAMURAa), Hiroyuki TABUCHIb), Shinya YODOYAb), Maki UMEDAc), Yoshio TAKAIa), Hitoshi YAMADAa), Hiroshi YAMAOKAc), Keiji HIROSEd), Yoshito TOBEd), Toshikazu TANAKAb), and Shigetoshi TAKAHASHIa)

    † This paper is dedicated to the memory of the late Professor Takekiyo MATSUO. *a) Materials Analysis Center, The Institute of Scientific and Industrial Research, Osaka University (8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan) b) Facully of Engineering, Osaka Institute of Technology (16-1 Omiya 5-chome, Asahi-ku, Osaka 535-0002, Japan) c) Department of Environmental Sciences, Faculty of Science, Osaka Women's University (2-1 Daisen-cho, Sakai, Osaka 590-0035, Japan) d) Graduate School of Engineering Science, Osaka University (1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan)
Chiral recognition ability of crown ether hosts toward organic amine salt guests has been evaluated using the FAB mass spectrometry coupled with our enantiomer-labeled guest method for the total 97 sets of chiral host-guest complexations. The hosts include various chiral crown ethers containing a dimethoxyphenyl group (1-16) and the related derivatives (17-22) and the guests include 1-(1-naphthyl)ethylamine salt (23) and α-amino acid methyl ester salts (24-28). In the case of the α-amino ester salt guests, the chiral crown ether (1 or 2) having sterically effective phenyl substituents as chiral barriers with a less flexible backbone-structure showed relatively higher degree of chiral recognition ability among the 22 chiral host series studied. On the other hand, toward the 1-(1-naphthyl)ethylamine salt guest, the most hosts gave relatively lower chiral recognition ability except for the specific hosts (6 and 7) having certain spatial constraint toward a complexing naphthyl group.
Key words: Chiral recognition, Host-guest complex, Deuterium labeling, Chiral crown ether, FAB mass spectrometry
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