Nucleophilic attack by oxyanions on a phosphate monoester dianion: The positive effect of a cationic general acid

…, MF Lima, D da Silva, F Nome

Index: Kirby, Anthony J.; Lima, Marcelo F.; Da Silva, Davi; Nome, Faruk Journal of the American Chemical Society, 2004 , vol. 126, # 5 p. 1350 - 1351

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Citation Number: 35

Abstract

The two negative charges on a phosphate monoester RO-PO32-at neutral pH provide a considerable electrostatic barrier toward reactions with nucleophilic reagents with a negative charge on the attacking atom. Electrostatic repulsion disappears when the hydrolysis of an aryl phosphate monoester is catalyzed by a neighboring cationic general acid. The hydrolysis of 8-dimethylammonium-1-phosphate (1) is catalyzed by oxyanions, ...