Functional micellar catalysis. Part 8. Catalysis of the hydrolysis of p-nitrophenyl picolinate by metal-chelating micelles containing copper(II) or zinc(II)

Abstract

The kinetic analysis of the esterolysis of p-nitrophenyl picolinate in neutral aqueous solutions of Cu²⁺ and Zn²⁺ in the presence of co-micelles made up of cetyltrimethylammonium bromide and either 6-(myristoylamido) methylpyridine-2-carboxylic acid (1) or 6-(myristoylamido)methyl-2-hydroxymethyl-pyridine (2) is reported. The results strongly indicate the formation of reactive micellar ternary complexes composed of metal ion, (1) or (2), and the substrate. The higher reactivity observed with co-micelles of (2) than that with those of (1) suggests that the metal ion in the ternary complex with (2) acts as a template for an intracomplex nucleophilic attack of the activated hydroxy function of (2) on the carbonyl of p-nitrophenyl picolinate.