Kinetic evidence for a methanolysis intermediate in aromatic nucleophilic substitution

Abstract

The reactions of 2,4- and 2,6-dinitrochlorobenzene and 2,4-dinitroanisole with cyclohexylamine in benzene and in methanol have been examined. Computer analysis of the kinetic data shows the formation and fate of solvolysis product in the reaction of 2,4-dinitrochlorobenzene in methanol. The results prove that an experimental failure to detect a solvolysis product is not evidence for a negligible solvolysis rate.