Micellar Effects upon the Hydrolysis of N-(Trifluoroacetyl)indole

Article abstract of DOI:10.1021/jo00318a016

The rate constants of acid hydrolysis of N-(trifluoroacetyl)indole (1) in 0.03 or 0.1 M HCl are slightly increased by anionic micelles of sodium lauryl sulfate (NaLS).From these data, and the distribution of hydrogen ions and substrate between water and the micelles, we estimate the second-order rate constant for the hydrogen ion reaction in the micellar pseudophase to be smaller than that in water by a factor of ca. 30.Cationic micelles of cetyltrimethylammonium bromide (CTABr) retard the acid hydrolysis, but they speed hydrolysis at pH 3-4, and their effect is reduced by NaCl or NaBr.Hydrolysis at pH 4.85 is inhibited by NaLS.These micellar effects can be interpreted in terms of mechanisms in which the hydrate of 1 is a key intermediate.