Unusual structure-energy correlations in intramolecular Diels-Alder reaction transition states

Justyna M. Żurek, Robert L. Rae, Martin J. Paterson, Magnus Bebbington

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Detailed analysis of calculated data from an experimental/computational study of intramolecular furan Diels-Alder reactions has led to the unusual discovery that the mean contraction of the newly forming C-C σ-bonds from the transition state to the product shows a linear correlation with both reaction Gibbs free energies and reverse energy barriers. There is evidence for a similar correlation in other intramolecular Diels-Alder reactions involving non-aromatic dienes. No such correlation is found for intermolecular Diels-Alder reactions.

Original languageEnglish
Pages (from-to)15535-15545
Number of pages11
JournalMolecules
Volume19
Issue number10
DOIs
StatePublished - 1 Oct 2014

Fingerprint

Diels-Alder reactions
Energy barriers
Cycloaddition Reaction
Gibbs free energy
furans
dienes
contraction
energy
products
furan

Keywords

  • Cycloaddition
  • Diels-Alder
  • Furan
  • Structure-energy correlation

Cite this

Żurek, Justyna M. ; Rae, Robert L. ; Paterson, Martin J. ; Bebbington, Magnus. / Unusual structure-energy correlations in intramolecular Diels-Alder reaction transition states. In: Molecules. 2014 ; Vol. 19, No. 10. pp. 15535-15545.
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Unusual structure-energy correlations in intramolecular Diels-Alder reaction transition states. / Żurek, Justyna M.; Rae, Robert L.; Paterson, Martin J.; Bebbington, Magnus.

In: Molecules, Vol. 19, No. 10, 01.10.2014, p. 15535-15545.

Research output: Contribution to journalArticleResearchpeer-review

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