Nucleophilic reactions in solutions of nonmicellized hydrophobic ammonium ions

Abstract

Abstract : Rate constants of reactions of p-nitrophenyl diphenyl phosphate, 2,4- dinitrochlorobenzene, and p-nitrophenyl benzoate with (2-hydroxyethyl)-tri-n- octylammonium bromide or mesylate in aqueous solvents at high pH can be treated quantitatively in terms of binding of reactants to nonmicellar aggregates and second-order rate constants of reaction in aggregates. These rate constants are very similar to those in cationic micelles, but micelles are the more effective at binding substrate. The apparent acid dissociation constant of the hydroxyl group is also larger in the micellar system. Keywords include: Nucleophilic reactions, Solutions, Ammonium ions, Reaction rates, Rate constants, Phosphates, Benzenes, and Benzoates.