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

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

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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

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Keywords

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

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