RATES OF DECARBOXYLATION OF SUBSTITUTED ANTHRANILIC ACIDS IN NITROBENZENE SOLUTION

Abstract

The synthesis of a series of meta- and para-substituted anthranilic acids is reported with their rates of decarboxylation in nitrobenzene solution at 210.5 °C. The reaction is second order with respect to anthranilic acid. The rate is increased by electron-releasing substituents and decreased by deuterium in the functional groups. The relative rates are interpreted by means of the Hammett equation and its extensions and it is concluded that the rate-determining step involves attack by proton from one anthranilic acid molecule on carbon 1 of a second molecule.