Micellar effects upon reactions of the 2,2',4,4',4''-pentamethoxytrityl cation with nucleophiles

Article abstract of DOI:10.1139/v86-195

Cationic micelles of cetyltrimethylammonium chloride and bromide (CTACl and CTABr) speed attack of water upon the 2,2',4,4',4''-pentamethoxytrityl cation by a factor fo ca. 5.The first-order rate constant in water is 5.51 s^-1 at 25.0 deg C.Anionic micelles of sodium dodecyl sulfate (SDS) have little effect on this reaction, but they strongly inhibit attack of OH^-.In water, second-order rate constants for attack of OH^-, CN^-, and N3^- are, respectively, 235, 177, and 2.8E5 M^-1s^-1.Rate constants of reaction in CTACl go through maxima with increasing and analysis of the data shows that second-order rate constants at the micellar surface are similar to those in water.