Kinetics and mechanism of ammonolysis and alkaline hydrolysis of naphthyl acetates in aqueous medium: Part II - 6-substituted 2-naphthyl acetates

摘要

Several 6-substituted 2-naphthyl acetates have been pepared and kinetics of their ammonolysis and alkaline hydrolysis studied at 20 deg. 25 deg and 30 deg C at various pH values in water with 1% dioxan at a definite ionic strength. The ammonolysis is first order in [free ammonia] and the process proceeds through a simple unassisted nucleophilic substitution pathway, which includes the zwitterionic tetrahedral intermediate (T~(+-)). In no case, is the catalysed pathwawy visible. The reason for the eabsence of expected catalysis in the case of ester with methyl substient is discussed.