Sulphur dioxide insertion into tin - Carbon bonds: solvent effects and the nature of the transition state

Fong, Clifford W. and Kitching, William (2014) Sulphur dioxide insertion into tin - Carbon bonds: solvent effects and the nature of the transition state. Journal of Physical Organic Chemistry, 27 3: 204-212. doi:10.1002/poc.3266


Author Fong, Clifford W.
Kitching, William
Title Sulphur dioxide insertion into tin - Carbon bonds: solvent effects and the nature of the transition state
Journal name Journal of Physical Organic Chemistry   Check publisher's open access policy
ISSN 0894-3230
1099-1395
Publication date 2014-01-01
Year available 2013
Sub-type Article (original research)
DOI 10.1002/poc.3266
Open Access Status Not Open Access
Volume 27
Issue 3
Start page 204
End page 212
Total pages 9
Place of publication Chichester, West Sussex, United Kingdom
Publisher John Wiley & Sons
Language eng
Abstract Data describing the insertion of sulphur dioxide into the carbon - tin bond of a range of substituted phenyltrimethyltin compounds in methanol and benzene solvents have been reconsidered. The reaction in methanol is cleanly second order, but the reaction in benzene has both a second-order and third-order component, the latter ascribable to an initial equilibrium formation of a SO2 complex with the phenyl ring followed by the insertion of a second SO2 molecule into the carbon-tin bond. Molecular orbital calculations have identified the transition states (TS) and the favoured reaction pathways for the second-order and third-order reaction pathways in benzene. The effects of solvents on TS and enthalpies of reaction have also been examined. New insights into the types of TS involved in electrophilic substitution reactions are revealed. Copyright
Keyword Kinetics
Molecular orbital computations
Organotin compounds
Solvent effects
Sulphur dioxide insertion
Transition states
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
 
Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 1 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 1 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Tue, 04 Mar 2014, 10:27:51 EST by System User on behalf of School of Chemistry & Molecular Biosciences