Understanding the mechanism of non-polar Diels-Alder reactions. A comparative ELF analysis of concerted and stepwise diradical mechanisms

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71 Citas (Scopus)

Resumen

The electron-reorganization along the concerted and stepwise pathways associated with the non-polar Diels-Alder reaction between cyclopentadiene (Cp, 1) and ethylene (2) has been studied using the topological analysis of the electron localization function (ELF) at the B3LYP/6-31G(d) level of theory. ELF results for the concerted mechanism stresses that the electron-reorganization demanded on the diene and ethylene reagents to reach two pseudo-diradical structures is responsible for the high activation energy. A comparative ELF analysis of some relevant points of the non-polar Diels-Alder reaction between Cp and styrene (10) suggests that these concerted mechanisms do not have a pericyclic electron-reorganization.

Idioma originalInglés
Páginas (desde-hasta)5495-5504
Número de páginas10
PublicaciónOrganic and Biomolecular Chemistry
Volumen8
N.º24
DOI
EstadoPublicada - 21 dic 2010

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Química física y teórica
  • Química orgánica

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