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Solvent Effects on Some Nucleophilic Substitutions

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Advances in Solution Chemistry

Abstract

The effects of hydroxylic solvents on △G≠ values for the solvolysis of t-butyl chloride have been dissected into initial-state and transition-state contributions. The △G°t(Tr) values, after correction for the “size” or “cavity” effect, are well correlated with values for the Me4N+ C1− ion-pair and for α-aminoacids. Similar calculations have been carried out for other alkyl halides and for SN2 reaction of triethylamine with ethyl iodide. Dissections of △H≠ and △S≠ for these SN1 and SN2 reactions into initial-state effects are also reported.

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Author information

Authors and Affiliations

  1. Department of Chemistry, University of Surrey, Guildford, UK

    Michael H. Abraham

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  1. Michael H. Abraham
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Editor information

Editors and Affiliations

  1. University of Florence, Florence, Italy

    I. Bertini  & A. Dei  & 

  2. University of Bologna, Bologna, Italy

    L. Lunazzi

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© 1981 Plenum Press, New York

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Abraham, M.H. (1981). Solvent Effects on Some Nucleophilic Substitutions. In: Bertini, I., Lunazzi, L., Dei, A. (eds) Advances in Solution Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-3225-1_24

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  • DOI: https://doi.org/10.1007/978-1-4613-3225-1_24

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-3227-5

  • Online ISBN: 978-1-4613-3225-1

  • eBook Packages: Springer Book Archive

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