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Rapid cleavage of phosphate triesters by the oxime 2‐(hydroxyimino)‐ N ‐phenyl‐acetamide
Author(s) -
Manfredi Alex M.,
Demos Willian,
Wanderlind Eduardo H.,
Silva Bárbara V.,
Pinto Angelo C.,
Souza Bruno S.,
Nome Faruk
Publication year - 2016
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3549
Subject(s) - chemistry , oxime , acetamide , paraoxon , phosphate , hydrolysis , medicinal chemistry , reaction rate constant , nucleophile , aqueous solution , stereochemistry , organic chemistry , kinetics , enzyme , acetylcholinesterase , physics , quantum mechanics , catalysis
We report the dephosphorylation reactions of the organophosphates diethyl 2,4‐dinitrophenyl phosphate ( DEDNPP ) and dimethyl 4‐nitrophenyl phosphate (methyl paraoxon) by the oxime 2‐(hydroxyimino)‐ N ‐phenyl‐acetamide ( Ox 1 ). Rate enhancements of 10 7 ‐fold over the rate constant for the spontaneous hydrolysis are observed in aqueous medium in presence of the anionic form of the oxime. Ox 1 represents a new family of nucleophiles which could be used for the degradation of toxic organophosphates. Copyright © 2016 John Wiley & Sons, Ltd.