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Chiral self‐discrimination of the enantiomers of α‐phenylethylamine derivatives in proton NMR
Author(s) -
Huang ShaoHua,
Bai ZhengWu,
Feng JiWen
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2406
Subject(s) - chemistry , enantiomer , proton nmr , proton , stereochemistry , quantum mechanics , physics
Two types of chiral analytes, the urea and amide derivatives of α‐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 © 2009 John Wiley & Sons, Ltd.