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KMID : 1059519900340060629
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Journal of the Korean Chemical Society
1990 Volume.34 No. 6 p.629 ~ p.636
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Chemical Reactions in Surfactant Solutions(Ⅲ). Nucleophilic and Micellar Catalyses on Hydrolysis of an Organic Phosphate by Sodium 2-Alkylbenzimidazole-5-sulfonates in Aqueous and CTABr Solutions
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Hong Young-Seuk
Park Hee-Hyun
Park Han-Seok
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Abstract
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Dephosphorylation of p-nitrophenyldiphenylphosphate(p-NPDPP) mediated by anions of sodium 2-alkylbenzimidazole-5-sulfonate(R-BI-SO3Na) in CTABr micellar solutions are obviously slower than that by anion of sodium benzimidazole-5-sulfonate(BI-SO3Na), and the reation rates were decreased with increase of lengths of alkyl groups. This presents a striking contrast to the reactions in aqueous solutions without added CTABr, of which the reaction rates are on approximately same levels. It seems due to steric effect of alkyl groups of R-BI-SO3Na in the Stern layer of micelle, and it is supported by measured activation parameters(△H≠, △G≠ and △S≠) of the reactions in aqueous and micellar solutions. In addition to nucleophilic ability of benzimidazole moiety of R-BI-SO3Na on the reactions, these compounds with long alkyl groups(nonyl to pentadecyl) are micellized for themseleves, and increase the reaction rates due to their micellar catalyses in aqueous solutions, not including CTABr.
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KEYWORD
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