Chiral self-discrimination of the enantiomers of alpha-phenylethylamine derivatives in proton NMR.

Shao-Hua Huang, Zheng-Wu Bai, Ji-Wen Feng

Index: Magn. Reson. Chem. 47(5) , 423-7, (2009)

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Abstract

Two types of chiral analytes, the urea and amide derivatives of alpha-phenylethylamine, were prepared. The effect of inter-molecular hydrogen-bonding interaction on self-discrimination of the enantiomers of analytes has been investigated using high-resolution (1)H NMR. It was found that the urea derivatives with double-hydrogen-bonding interaction exhibit not only the stronger hydrogen-bonding interaction but also better self-recognition abilities than the amide derivatives (except for one bearing two NO(2) groups). The present results suggest that double-hydrogen-bonding interaction promotes the self-discrimination ability of the chiral compounds.Copyright (c) 2009 John Wiley & Sons, Ltd.