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

✍ Scribed by Shao-Hua Huang; Zheng-Wu Bai; Ji-Wen Feng

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
121 KB
Volume
47
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

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.

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## Abstract α‐Cyclodextrin was shown to be convenient chemical shift reagent for determination of the enantiomeric composition of α‐hydroxyphosphonic acids by means of ^31^P NMR. The developed methodology appeared to be reliable, repetitive, easy to perform and simple for interpretation. Enantiomer