Studies on nitroaromatic compounds. Part 8. A kinetic and spectroscopic study of the reaction of di- and tri-ethylamine with 1,5-dimethyl-2,4,8-trinitronaphthalene

Abstract

The reaction of 1,5-dimethyl-2,4,8-trinitronaphthalene with diethylamine and triethylamine in DMSO and in DMSO–MeOH solvent systems has been studied. ¹H N.m.r. investigations have shown that a benzyl type anion is formed due to hydrogen abstraction from the 1-methyl group of the nitroaromatic compound. Kinetic and thermodynamic data for the systems have been determined. The results are explained in terms of the difference in solvation of the two amines and the charged products and the difference in solvating ability of the solvent media used. The effect of added triethylammonium chloride on the reaction of 1,5-dimethyl-2,4,8-trinitronaphthalene with triethylamine in DMSO has been studied and the change in kinetics is attributed to ion association between the added salt and the charged products.