Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase

摘要

To understand the selectivity of the crown ether type chiral stationary phase (CSP), theretention selectivity for aniline and the positional isomers of substituted anilines were studied. Invarious substituted isomers, except nitroaniline, a remarkable decrease of retention due to sterichindrance was observed for the 2-substituted isomer. To determine the detailed molecular recog-nition mechanism, quantum chemical calculations were performed for the aggregates between thecrown ether and the anilines. The results suggested that the 20-Crown-6, which includes a phe-nyl-substituted 1,1′-binaphthyl moiety, interacts with alkyl and aryl amines in an unconventionalform different from the proposed one for 18-Crown-6.