Micellar Catalysis of the Basic Hydrolysis of Amides. 4. Substituted N,N-Diphenylbenzamides

Article abstract of DOI:10.1021/jo00330a029

The cytalysis of the basic hydrolysis of a series of N-aryl-N-phenylbenzamides (1) and a series of substituted N,N-diphenylbenzamides (2) by micelles of cetyltrimethylammonium bromide (ctab) has been studied.On the basis of the effects of substituents on the aromatic ring attached to the nitrogen atom, a mechanistic change on transfer from water to a micellar environment is proposed.In water the mechanism involves rate-determining solvent-assisted carbon-nitrogen bond breaking (mechanism B), while in the presence of micelles of ctab, a rate-determining attack of hydroxide ion (mechanism C) is proposed.Reasons for mechanistic change are discussed.