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What is the stabilizing interaction with nucleophilic solvents in the transition state for solvolysis of tertiary derivatives: Nucleophilic solvent participation or nucleophilic solvation?

  • SUNY Buffalo

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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 languageEnglish
Pages (from-to)2225-2228
Number of pages4
JournalOrganic Letters
Volume3
Issue number14
DOIs
StatePublished - Jul 12 2001

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