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Ring-substituted benzohydroxamic acids: 1H, 13C and 15N NMR spectra and NHOH proton exchange

✍ Scribed by Jan Schraml; Marcela Tkadlecová; Statis Pataridis; Ludmila Soukupová; Vratislav Blechta; Jana Roithová; Otto Exner

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
158 KB
Volume
43
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

NMR spectra (^1^H, ^13^C, ^15^N) of para‐ and meta‐substituted benzohydroxamic acids were studied in dry dimethyl sulfoxide solutions. The ^13^C chemical shifts were very close to those found by cross‐polarization magic angle spinning in solids, the hydroxamic (not hydroximic) structure of which is unambiguous. The hydroxamic structure of these acids in DMSO solutions was proved independently by their ^15^N chemical shifts. The ^15^N and ^1^H chemical shifts of the NHOH fragment showed excellent mutual dependences and dependences on the nature of the ring substituent. According to these dependences and ab initio energy calculations, all the acids assume the same Z conformation. Proton exchange between hydroxamic OH and NH groups in DMSO proceeded by both intra‐ and intermolecular exchange and the rates did not exhibit any simple relationship to the substituent constants. Copyright © 2005 John Wiley & Sons, Ltd.

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