THE EFFECT OF 2-METHYL-SUBSTITUTED NITROIMIDAZOLES ON THE HYDROLYSIS OF 4-NITROPHENYL ESTERS

Authors
  1. Clewley, R.G.
  2. Adie, C.P.
  3. Brouwer, B.H.
Corporate Authors
Defence Research Establishment Suffield, Ralston ALTA (CAN)
Abstract
Prior to investigating nitroimidazole surfactants for use in a new catalytic chemical agent decontaminant, the cataly is afforded by simple nitroimidazoles in hydrolysis reactions has been examined. The effect of 2-methyl-5-nitroimidazole on the hydrolysis of 4-nitrophenyl and of 2-methyl-5-nitrobenzimidazole on the hydrolyses of both 4-nitrophenyl diphenylphosphinate and 4-nitrophenyl acetate has been determined. In all three cases there is a simple linear dependency of the reaction rate on the concentration of the anionic form of the nitroimidazole. Previous results had suggested self-inhibition by the nucleophile occurred in the 2-methyl-5-nitroimidazole catalysed hydrolysis of 4-nitrophenyl diphenylphosphinate; this hypothesis is no longer tenable. Comparison of the reactivity of 2-methy-substituted nitroimidazolides to that of the corresponding unsubstituted species suggests that 2-alkyl-substituted nitroimidazole surfactants would not be significantly worse catalysts of the hydrolysis of organophosphorus species than their 4-substituted analogues.
Keywords
Nitroimidazoles;Phenoxides
Report Number
DRES-603 —
Date of publication
01 Mar 1994
Number of Pages
39
DSTKIM No
94-03247
CANDIS No
142379
Format(s):
Hardcopy;Originator's fiche received by DSIS

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