Carboxylic and phosphate ester hydrolysis catalysed by bivalent zinc and copper metallosurfactants

Abstract
The syntheses of three new lipophilic ligands are reported: Nα-(1,10-phenanthrolin-2-ylmethyl)-Nτ-dodecylhistamine (1), N-dodecyl-2-aminomethyl-1,10-phenanthroline (2), and Nα-(2-pyridylmethyl)-Nτ-dodecylhistamine (3). Mixed micellar systems made of complexes of these ligands with ZnII and CuII in the presence of an inert cosurfactant (CTABr or Brij 35) are efficient catalysts in the hydrolysis of p-nitrophenyl picolinate (PNPP) and diphenyl-p-nitrophenyl phosphate (DPPNPP). Kinetic studies strongly indicate the formation of a reactive ternary complex composed of metal ion, ligand, and substrate. These synzymes operate via a metal–hydroxide-ion catalysed mechanism and exhibit turn-over behaviour while retaining their full catalytic activity.

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