Acyl derivatives of hydroxylamine. Part XVII. Dipole moments, configuration, and conformation of benzohydroxamoyl chlorides

Abstract

The dipole-moment data of eleven aromatic hydroxamoyl chlorides, measured in benzene, have been analysed in terms of the configuration of the CN bond and conformation on the N–O bond. The total group moment of the –C(Cl)NOH grouping amounts to 1·65 D and lies at the angle of 49° to the C_ar–C bond. Although the reasoning is more complex and agreement of computed and experimental values somewhat worse than in similar cases, it is concluded that the most probable form is E_ap(anti-periplanar). Hence the stable configuration is different from that of oximes and seems to be controlled by other factors than purely steric ones.