ALKALINE HYDROLYSIS OF ALKYL ESTERS OF BENZOIC, 1- AND 2-NAPHTHOIC, 1-, 2-, AND 9-ANTHROIC, AND 1-, 2-, 3-, 4-, AND 9-PHENANTHROIC ACIDS

The rate coefficients for the alkaline hydrolysis of methyl carboxylic esters in ' 70% dioxan ' solution follow the sequence: 2-phenanthryl > 2-anthryl > 3-phenanthryl > phenyl > 2-naphthyl > 9-phenanthryl > 1-naphthyl > 1-phenanthryl > 1-anthryl ≫ 4-phenanthryl > 9-anthryl. A series of alkyl benzoates, and higher esters of several of the polycyclic aromatic carboxylic acids have also been studied. Electronic and steric effects on rate, on enthalpy of activation, and on entropy of activation, are discussed.