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NMR study of E/Z isomerism in N-alkoxybenzoimidic acid derivatives

✍ Scribed by Jan Schraml; Vratislav Blechta; Jindřich Karban; Jaromir Mindl

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
103 KB
Volume
40
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Well defined E/Z isomers of N‐methoxy‐p‐nitrobenzimidoyl chloride, N‐methoxybenzimidoyl chloride, methyl N‐methylbenzohydroximate and ethyl N‐hydroxybenzimidate were prepared in order to provide model data for studies of benzhydroximic acid derivatives and related compounds. NMR parameters [^1^H, ^13^C and ^15^N chemical shifts and ^1^J(^13^C, ^13^C) coupling constants] were determined. The results show that stereochemically most significant are the values of ^1^J(^13^C, ^13^C) couplings between aromatic C~ipso~ and CN carbons and that the relationship, |J~cis~| > |J~trans~|, known for this coupling from oximes, is not affected by electronegative substituents at the CN carbon atom, but the values are. Copyright © 2002 John Wiley & Sons, Ltd.

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