Abstract
The kinetics of the reversible hydration of 1,3-dichloroacetone catalysed by Aerosol-OT-solubilized perchloric acid, DClO4, imidazole (Imz), and N-methylimidazole (Melmz) have been studied in carbon tetrachloride. Rate constants for acid-catalysed hydration are higher in the presence of the detergent than in acid–dioxan mixtures. The average rate enhancement is 15.6 for perchloric acid catalyst and 14.2 for DClO4. Hydration equilibrium constants are also higher in the presence of Aerosol-OT than in water– or D2O–dioxan mixtures. Compared with the Imz- and Melmz-catalysed reactions in aqueous dioxan, the surfactant increases the rate constants by factors of 209 and 144. The results are interpreted in terms of the properties of the Aerosol-OT-solubilized water, acids, and bases, as well as of the role played by the hydrophilic groups of the surfactant.
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More From: Journal of the Chemical Society, Perkin Transactions 2
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