The reaction of N-t-Butyl-2,4,6-trinitrobenzamide with sodium hydroxide. A unimolecular nucleophilic aromatic substitution

Abstract

N-t-Butyl-2,4,6-trinitrobenzamide undergoes a nucleophilic substitution with hydroxyl ions to form nitrite ions. The amide is stable during this reaction and will only undergo hydrolysis under the more drastic conditions of higher hydroxyl ion concentrations at higher temperatures. The observed rate of the nucleophilic substitution is inversely proportional to the hydroxyl ion concentration. In the presence of alkali, the amide is in equilibrium with a red anionic complex and the equilibrium constant has been calculated from the kinetic data. When allowance has been made for this equilibrium, it is found that the formation of nitrite ions from the amide is zero order with respect to the hydroxyl ion concentration.