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Int. J. Mol. Sci. 2008, 9(9), 1704-1716; doi:10.3390/ijms9091704
Article

The Influence of Carbon-Carbon Multiple Bonds on the Solvolyses of Tertiary Alkyl Halides: a Grunwald-Winstein Analysis

1
,
2
 and
1,*
Received: 17 June 2008 / Revised: 4 August 2008 / Accepted: 26 August 2008 / Published: 4 September 2008
(This article belongs to the Special Issue Grunwald-Winstein Equations – 60 Years & Counting)
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Abstract

The influence of carbon-carbon multiple bonds on the solvolyses of 3-chloro-3-methylbutyne (1), 2-chloro-2-phenylpropane (2), 2-bromo-2-methyl-1-phenylpropane (3), 4-chloro-4-methyl-2-pentyne (4) and 2-chloro-2-methylbutane (5) is critically evaluated through the extended Grunwald-Winstein equation. Substrates 1, 3 and 5 lead to correlations with unexpected negative sensitivity, h, to changes in the aromatic ring parameter, I. It is claimed that I is not a pure parameter, reflecting also some solvent nucleophilicity, NOTs, character. In substrates 2 and 4 the possibility of rearside solvation is reduced due to steric hindrance and/or cation stabilization and the best found correlations involve only the solvent ionizing power, Y, and I.
Keywords: Grunwald-Winstein Equation; Solvent effects; Carbon-carbon multiple bonds; Tertiary alkyl halides Grunwald-Winstein Equation; Solvent effects; Carbon-carbon multiple bonds; Tertiary alkyl halides
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Reis, M.C.; Elvas-Leitão, R.; Martins, F. The Influence of Carbon-Carbon Multiple Bonds on the Solvolyses of Tertiary Alkyl Halides: a Grunwald-Winstein Analysis. Int. J. Mol. Sci. 2008, 9, 1704-1716.

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