Micellar catalysis of anilide hydrolysis

Abstract

The rate of hydrolysis of several anilides is catalysed by cationic micelles (cetyltrimethylammonium bromide), and inhibited by anionic micelles (sodium lauryl sulfate). The magnitude of catalysis is greatest for those anilides which contain the most hydrophobic R groups (R = C₇H₁₅ and Ph) and is less for those containing less hydrophobic R groups (R = Me). The magnitude of catalysis is greater for compounds activated by nitro groups than for those activated by a ring nitrogen atom. The catalysis is inhibited by added sodium bromide. There is no evidence that anilide hydrolysis in a micellar environment involves dianionic intermediates. Micellar catalysis of anilide hydrolysis is much greater than for ester hydrolysis.