Nucleophilic cleavage of the silicon–oxygen bond: acid-catalysed hydrolysis of tributylphenoxysilanes in aqueous organic solvents
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1324-1331
- https://doi.org/10.1039/p29740001324
Abstract
The kinetics of acid-catalysed hydrolysis of tributylphenoxysilanes have been studied in aqueous dioxan, aqueous propan-2-ol, and aqueous acetonitrile. In aqueous dioxan, when allowance has been made for changes of acidity functions with solvent composition, the hydrolysis is shown to be at least second-order in water. Substituent effects are consistent with a mechanism involving fast protonation of the phenoxysilane followed by rate-limiting hydrolysis of the protonated species. The similarity of rates of hydrolysis in each solvent indicates that solvation differences between initial and transition states are either small or constant.Keywords
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