Proton nuclear magnetic resonance studies of the products formed by polynitrobenzenes when dissolved in liquid ammonia

Abstract

Proton n.m.r. spectra of the solutions formed by dissolving various polynitro- and substituted polynitro-benzenes in liquid ammonia have been measured. Products, with Meisenheimer-like structures, formed by nucleophilic attack of NH₂^– on the solutes have been identified. In a number of cases, attack by a second NH₂^– ion occurs. Some of the products show geometrical isomerism. With 2,4,6-trinitrotoluene there is no evidence for the formation of the carbanion formed by loss of a proton from the methyl group of 2,4,6-trinitrotoluene.