Rapid cleavage of phosphate triesters by the oxime 2-(hydroxyimino)-N-phenyl-acetamide

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 107‐fold over the rate constant for the spontaneous hydr...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2016-11, Vol.29 (11), p.600-603
Main Authors: Manfredi, Alex M., Demos, Willian, Wanderlind, Eduardo H., Silva, Bárbara V., Pinto, Angelo C., Souza, Bruno S., Nome, Faruk
Format: Article
Language:English
Subjects:
dephosphorylation
detoxification
organophosphate
oxime
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Summary: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 107‐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. A rapid rate of dephosphorylation of toxic organophosphates promoted by an oxime was observed in aqueous solution, which could lead to the development of applicable antidotes for human poisoning by organophosphorus compounds.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.3549