Unstable intermediates. Part 116.—Radical anions of N-halogenated amides

Abstract

Exposure to γ radiation of powdered or single crystal samples of N-chloro- and N-bromo-succinimide, and of N-bromoacetamide, at 77 K gave paramagnetic species whose e.s.r. spectra were characteristic of radicals having an unpaired electron predominantly in a N-Hal σ* orbital, almost equally distributed between the nitrogen and halogen atoms. These radicals are, therefore, identified as the radical anions of the amides. Alternative structures are considered and these anions are contrasted with those derived from corresponding carbonyl compounds.