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Molecules 2014, 19(10), 15535-15545;

Unusual Structure-Energy Correlations in Intramolecular Diels–Alder Reaction Transition States

Institute of Chemical Science, School of Engineering and Physical Sciences, William Perkin building, Heriot-Watt University, Edinburgh EH14 4AS, UK
Authors to whom correspondence should be addressed.
Received: 23 July 2014 / Revised: 1 September 2014 / Accepted: 16 September 2014 / Published: 29 September 2014
(This article belongs to the Special Issue Cycloaddition Chemistry)
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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. View Full-Text
Keywords: cycloaddition; Diels–Alder; furan; structure-energy correlation cycloaddition; Diels–Alder; furan; structure-energy correlation

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Żurek, J.M.; Rae, R.L.; Paterson, M.J.; Bebbington, M.W.P. Unusual Structure-Energy Correlations in Intramolecular Diels–Alder Reaction Transition States. Molecules 2014, 19, 15535-15545.

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