Density functional theory study of selective deacylation of aromatic acetate in the presence of aliphatic acetate under ammonium acetate mediated conditions.

Aromatic acetates can be selectively deprotected in the presence of aliphatic acetates under ammonium acetate mediated condition. B3LYP/6-31++G** level of theory was demonstrated to be successfully used to model the relative reaction rates for deacylation reactions for aliphatic and aromatic ester systems. On the basis of the mechanistic studies, acetate anion is most likely to be the active catalyst for the ester deacylation reactions under ammonium acetate mediated condition.