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

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

1
Department of Chemistry and Biochemistry, Sciences Faculty, University of Lisbon, CQB, Campo Grande, 1749-016 Lisboa, Portugal
2
Department of Chemical Engineering, Lisbon Institute of Engineering, IPL, R. Conselheiro Emídio Navarro, 1, 1959-007 Lisboa, Portugal
*
Author to whom correspondence should be addressed.
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 (CC BY 3.0).

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MDPI and ACS Style

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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