Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions

Luis R. Domingo, M. José Aurell, Patricia Pérez, Renato Contreras

Research output: Contribution to journalArticlepeer-review

627 Citations (Scopus)

Abstract

The global electrophilicity power, ω, of a series of dienes and dienophiles commonly used in Diels-Alder reactions may be conveniently classified within a unique relative scale. Useful information about the polarity of transition state structures expected for a given reaction may be obtained from the difference in the global electrophilicity power, Δω, of the diene/dienophile interacting pair. Thus the polarity of the process can be related with non-polar (Δω small, pericyclic processes) and polar (Δω big, ionic processes) mechanisms.

Original languageEnglish
Pages (from-to)4417-4423
Number of pages7
JournalTetrahedron
Volume58
Issue number22
DOIs
Publication statusPublished - 27 May 2002

Keywords

  • Density functional theory
  • Diels-Alder reactions
  • Electrophilicity power

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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