Solvent effects upon the rates of acid-induced decomposition of 3-methyl-1-p-tolyltriazene and diphenyldiazomethane

Abstract

Rates of reaction of 3-methyl-1-p-tolyltriazene with benzoic acid to form methyl benzoate, p-toluidine, and nitrogen have been measured in a wide variety of aprotic solvents. Similar studies are also reported on the reactions of diphenyldiazomethane with benzoic acid and with p-nitrophenol. Large solvent effects upon all reactions are observed; those of the triazene correlate well with the donor character of the solvent as expressed by several empirical parameters. The reactions of diphenyldiazomethane appear to be better interpreted by a multiple correlation with both donor and polar (electrostatic) contributions to the solvent effect.