Journal of Organic Chemistry p. 3522 - 3525 (1981)
Update date:2022-08-05
Topics:
Broxton, Trevor J.
Fernando, Denise R.
Rowe, Jeffrey E.
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.
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Doi:10.1021/jm00138a010
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