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| Content Provider | Royal Society of Chemistry (RSC) |
|---|---|
| Author | Cockerill, Anthony F. Banger, J. Davies, G. L. O. |
| Copyright Year | 1971 |
| Abstract | The rate coefficients for elimination from 24 substrates in the series 2-Z-phenylethyl p-Y-arenesulphonate with potassium t-butoxide in t-butyl alcohol at 40 °C have been correlated with the Hammett equation. The reaction constants ρz decrease linearly with the electronic properties of the group Y only for the most electron-withdrawing substituents, indicative of a shift to transition states with less carbanion character. The reaction constants ρY become less positive as Z becomes more electron-withdrawing, suggesting that increased Cβ–H bond breaking is accompanied by decreased Cα–X bond breaking, and a shift to a transition state with greater carbanion character. This result supports earlier secondary deuterium isotope studies in establishing a new interpretation of the reactivity ratio kOTs/kBr as a measure of C–X bond breaking. |
| Starting Page | 498 |
| Ending Page | 502 |
| Page Count | 5 |
| File Format | |
| ISSN | 00456470 |
| Volume Number | 0 |
| Journal | Journal of the Chemical Society B: Physical Organic |
| DOI | 10.1039/J29710000498 |
| Language | English |
| Publisher | Royal Society of Chemistry |
| Access Restriction | Open |
| Subject Keyword | Hammett Reaction rate constant Potassium tert-butoxide Hammett equation Carbanion Chemical bond Deuterium Isotope |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Physical and Theoretical Chemistry |
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