Abstract
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.
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