Micellar effects upon reactions of the 2,2′,4,4′,4″-pentamethoxytrityl cation with nucleophiles
Open Access
- 1 June 1986
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 64 (6) , 1179-1183
- https://doi.org/10.1139/v86-195
Abstract
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 of ca. 5. The first-order rate constant in water is 5.51 s−1 at 25.0 °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 2.8 × 105 M−1 s−1. Rate constants of reaction in CTACl go through maxima with increasing [surfactant] and analysis of the data shows that second-order rate constants at the micellar surface are similar to those in water.Keywords
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