Series nucleophilic catalysis in the hydrolysis of 3-acetoxyphthalate. Intramolecular catalysis of ester hydrolysis by the carboxyl group once removed

Electrostatic Basis of Enzyme Catalysis

“…These model compounds seem to indicate that proximity effects can account for rate enhancement by a factor of 10 10 or more (Fersht and Kirby, 1968). For example, in the model compound of Figure 1 the relative rate of intermolecular vs. intramolecular acetyl migration is 10 8 thus proximity of the reacting groups can be an important determinant of rate acceleration.…”