87810-32-0Relevant articles and documents
Intramolecular General Acid Catalysis of Intramolecular Nucleophilic Catalysis of the Hydrolysis of a Phosphate Diester
Abell, Katherine W. Y.,Kirby, Anthony J.
, p. 1171 - 1174 (1983)
The dianion (8) of bis-2-carboxyphenyl phosphate (half-life 10.2 min at 39 deg C) is hydrolysed ca. 1E10 times faster than diphenyl phosphate.The reaction is accounted for in terms of intramolecular general acid catalysis by the ortho-CO2H of one salicyl group of the breakdown of the penta-covalent intermediate formed by the addition to phosphorus of the carboxylate group of the other.The general acid catalysis part of the process is unexpectedly inefficient.