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| Content Provider | Royal Society of Chemistry (RSC) |
|---|---|
| Author | Abraham, M. H. |
| Copyright Year | 1971 |
| Abstract | Standard free energies of transfer from ethyl benzoate to 17 other solvents of trimethylamine, p-nitrobenzyl chloride, and the trimethylamine–p-nitrobenzyl chloride transition state have been calculated (at 298 K). The transition state is stabilised by polar solvents and is destabilised by non-polar solvents; dipolar aprotic solvents are much more effective in stabilising the transition state than are the aliphatic alcohols. Similar calculations have been carried out for the substitution of o-, m- and p-nitrobenzyl chlorides by trimethylamine for 6 solvents (at 303 K). A comparison of solvent effects on the free energy of the trimethylamine–p-nitrobenzyl chloride transition state, the t-butyl chloride solvolysis transition state, and the Et4N+l– ion pair indicates that the solvolysis transition state markedly resembles an ion pair in behaviour, but that the transition state for substitution of p-nitrobenzyl chloride by trimethylamine is very much less polar. |
| Starting Page | 299 |
| Ending Page | 308 |
| Page Count | 10 |
| File Format | |
| ISSN | 00456470 |
| Volume Number | 0 |
| Journal | Journal of the Chemical Society B: Physical Organic |
| DOI | 10.1039/J29710000299 |
| Language | English |
| Publisher | Royal Society of Chemistry |
| Access Restriction | Open |
| Subject Keyword | Ethyl benzoate Trimethylamine Chloride Aliphatic compound Solvent Gibbs free energy Tert-Butyl chloride Solvolysis Ion |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Physical and Theoretical Chemistry |
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