The stabilities of Meisenheimer complexes. Part 22. The ionisation of 2,4-dinitroaniline, its N-alkylated derivatives, and 2,6-dinitroaniline in methanol–dimethyl sulphoxide containing sodium methoxide

Abstract

2,4-Dinitroaniline and its N-alkylated derivatives react with sodium methoxide in methanol–dimethyl sulphoxide to give the conjugate base. However, in the case of 2,6-dinitroaniline, base addition at the 3-position competes with proton loss. The effects of N-alkylation on the acidity of 2,4-dinitroaniline are considered and are compared with the effects of similar substitution in 2,4,6-trinitroaniline.