87799-87-9Relevant academic research and scientific papers
Participation of two carboxyl groups in phosphodiester hydrolysis. 1. hydrolysis of bis(2-carboxyphenyl) phosphate
Bruice, Thomas C.,Blaskó, Andrei,Petyak, Mark E.
, p. 12064 - 12069 (2007/10/03)
The energies of rotamer conformations of bis(2-carboxyphenyl) phosphate (2), where one o-carboxy group is ionized and the other is not, have been determined by semiempirical (SAM1, AM1/SM2.1) calculations in order to approximate the probability of the pre
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 (2007/10/02)
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.
