Study of the Pyridine 1-Oxide-Catalyzed Two-Phase Reversible Exchange Reaction of Benzoyl Chloride and Butanoate Ion

Abstract

Abstract The reaction of benzoyl chloride (PhCOCl) and butanoate ion (PrCOO−) catalyzed by pyridine 1-oxide (PNO) in the medium H2O/CH2Cl2 leads to equilibrium with butanoyl chloride (PrCOCl) and benzoate ion (PhCOO−) and vice versa. The rate-determining step takes place in the organic phase and PrCOCl is much more reactive than PhCOCl. The effects of chloride ion, hydroxide ion, pyridine 1-oxide, reactants and temperature on the reaction rate and the equilibrium conversion of acyl chloride (RCOCl) were investigated. Satisfactory detailed mechanistic interpretations of the kinetic results are given.