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

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 [1H, 13C and 15N chemical shifts and 1J(13C, 13C) coupling constants] were determined. The results show that stereochemically most significant are the values of 1J(13C, 13C) couplings between aromatic Cipso and CN carbons and that the relationship, |Jcis| > |Jtrans|, 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.