BIBLIOS

Document type
Journal articles

Document subtype
Full paper

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

Participants in the publication
M. C. Reis (Author)
R. Elvas-Leitão (Author)
F. Martins. (Author)
Dep. Química e Bioquímica
CQB

Summary
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.


Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES

Publication Identifiers
ISSN - 1422-0067

Publisher
MDPI

Collection
Special Issue Grunwald-Winstein Equations – 60 Years & Counting



Document Identifiers
DOI - https://doi.org/10.3390/ijms9091704

Rankings
SCIMAGO Q3 (2008) - 0.305 - Physical and Theotretical Chemistry
Web Of Science Q3 (2008) - 0.978 - Chemistry, Multidisciplinary

Keywords
Grunwald-Winstein Equation Solvent effects Carbon-carbon multiple bonds Tertiary alkyl halides

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