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Peroxyhydrolysis of 4-nitrophenyl diethyl phosphate in micellar systems based on imidazolium gemini surfactants

Theoretical and Experimental Chemistry(2012)

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Abstract
The nucleophilic reactivity of HO – and HOO – ions in the presence of imidazole gemini surfactants toward 4-nitrophenyl diethyl phosphate (NPDEP) was studied. It was shown that in the micelles of these detergents, as in water, an α effect is realized for the hydroperoxide ion. Its magnitude, characterized by the ratio of the second-order rate constants k 2(HOO-) m / k 2(HO-) m for the reaction with NPDEP in the micellar pseudophase, reaches ~100. Comparable micellar effects are observed at concentrations of the gemini surfactants not less than an order of magnitude lower than in the case of their monomeric analogs.
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Key words
imidazolium gemini surfactants,4-nitrophenyl diethyl phosphate,hydroxide and hydroperoxide anions,nucleophilicity,α effect,micellar effect.
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