Rapid cleavage of phosphate triesters by the oxime 2‐(hydroxyimino)‐ N ‐phenyl‐acetamide | Zendy

Manfredi Alex M. | Zendy; Demos Willian | Zendy; Wanderlind Eduardo H. | Zendy; Silva Bárbara V. | Zendy; Pinto Angelo C. | Zendy; Souza Bruno S. | Zendy; Nome Faruk | Zendy

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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.

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