Buffer Catalysis of the Trifluoroethanolysis of Phenoxydimethylphenylsilane

Article abstract of DOI:10.1021/jo00051a032

The acetic acid-acetate catalyzed trifluoroethanolysis of phenoxydimethylphenylsilane at constant ionic strength was studied.Plots of k_obs against total buffer concentration at a constant ratio of acid to base show upward curvature.The upward curvature is consistent with the trifluoroethanolysis occurring by three mechanisms involving (1) general acid catalysis, (2) general base catalysis, and (3) bifunctional acid-base catalysis.The observation of bifunctional catalysis is consistent with the trifluoroethanolysis of phenoxydimethylphenylsilane occurring by a concerted mechanism, involving a single transition state.