PCM/B3LYP/6-311++G**//B3LYP/6-31++G** level of theory was verified with reported experimental results and applied to study the mechanism and kinetics of deacylation reactions for ester systems under ammonium acetate mediated conditions.  Based on the mechanistic studies, the acetate anion is identified as the active catalyst for the ester deacylation reactions under ammonium acetate mediated conditions.  Computational results showed that the intrinsic kinetics of the deprotection reaction for aromatic acetate are much faster (5.4*E3) than that for aliphatic acetate at 25 �C, which is consistent with experimental results.  Several functionalized acetates and benzoates have also been kinetically studied under acetate anion catalytic mechanism to demonstrate different types of esters present significant different deacylation kinetics.

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

244th National Meeting (2012)

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