Abstract
(Matrix presented) We propose that controversy concerning the mechanism for solvolysis at tertiary carbon is semantic and can be avoided by making a clear distinction between (1) nucleophilic solvent participation, which is stabilization of the transition state for concerted solvolysis by formation of a partial covalent bond to the solvent nucleophile, and (2) nucleophilic solvation, which is stabilization of the transition state for stepwise solvolysis through carbocation or ion pair intermediates by charge-dipole interactions with nucleophilic solvents.
| Original language | English |
|---|---|
| Pages (from-to) | 2225-2228 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 3 |
| Issue number | 14 |
| DOIs | |
| State | Published - Jul 12 2001 |
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