Acyl derivatives of hydroxylamine. Part XVIII. Configuration and conformation of benzamidoximes

Abstract

The configuration and conformation of some benzamidoximes have been established from electric dipole moments measured in benzene and from the n.m.r. spectra in [²H₆]dimethyl sulphoxide. The results of the two experimental approaches are complementary and compatible with a hydroxyimino-tautomeric structure as well as with a Z-configuration for the CN bond. Most of the compounds examined exist in a single, almost planar conformation (D); for ortho-phenyl substituted derivatives only the conformational equilibrium (D)⇄(H) takes place.