Correlation of the rates of solvolysis of tert-butyl chlorothioformate and observations concerning the reaction mechanism
Open Access
- 30 September 2012
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 3 (3), 267-272
- https://doi.org/10.5155/eurjchem.3.3.267-272.624
Abstract
The “parent” tertiary alkyl chloroformate, tert-butyl chloroformate, is unstable, but the tert-butyl chlorothioformate (1) is of increased stability and a kinetic investigation of the solvolyses is presented. Analyses in terms of simple and extended Grunwald-Winstein equations are carried out. The original one-term equation satisfactorily correlates the data with sensitivity towards changes in solvent ionizing power of 0.73±0.03. When the two-term equation is applied, the sensitivity towards changes in solvent nucleophilicity of 0.13±0.09 is associated with a high (0.17) probability that the term that it governs is not statistically significant.Keywords
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