Micellar catalysed hydrolysis of amides. II. N-Ethyl-4-nitrotrifluoroacetanilide in functional and non-functional micelles

Abstract

The reactivity of N-ethyl-4-nitrotrifluoroacetanilide has been examined in the presence of a non-functional detergent (n- hexadecyltrimethylammonium bromide) and three functional detergents, n-hexadecyl(2-hydroxyethyl)dimethylammoniumchloride, n- hexadecyl(imidazol-4-ylmethyl)dimethyl-ammonium chloride and n-hexadecyl(2-hydroxyethyl)(imidazol-4-ylmethyl)methylammonium chloride, at 293.5 K and in borate buffer (1.3 × 10-3 mol dm-3, pH 9.0). The variation of the rate constants for the overall reaction with surfactant concentration has been analysed in terms of the reactant concentrations and rate constants in each pseudophase, the micelle binding constant and the critical micelle concentration, CMC. Surface tension measurements have been made on solutions of these surfactants. The values of CMC have been measured with, and without, the addition of a kinetic concentration of amide and the results compared with those from the kinetic analysis.