Structural studies on isolable (E)- and (Z)-NN-disubstituted-amidoximes. Crystal and molecular structure of (E)-morpholino-p-nitrobenzamidoxime

Abstract

Dipole-moment and n.m.r. measurements are used to assign the structure of the NN-disubstituted-amidoximes formed from nitrile oxides and secondary amines under kinetic control; these have the Z-configuration. The thermodynamically more-stable isomers were also isolated and shown to have the E-configuration; this structure was confirmed in one case by X-ray crystallography. The factors which determine amidoxime stability are discussed.