Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions

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

Research output: Contribution to journalArticlepeer-review

269 Citations (Scopus)

Abstract

The global electrophilicity power, ω, of a series of dipoles and dipolarophiles commonly used in 1,3-dipolar cycloadditions may be conveniently classified within a unique relative scale. The effects of chemical substitution on the electrophilicity of molecules have been evaluated using a representative set of electron-withdrawing and electron-releasing groups for a series of dipoles including nitrone, nitrile oxide and azide derivatives. The absolute scale of electrophilicity is used to rationalize the chemical reactivity of these species as compared to the static reactivity pattern of the reagents involved in the Diels-Alder reactions.

Original languageEnglish
Pages (from-to)3117-3125
Number of pages9
JournalTetrahedron
Volume59
Issue number17
DOIs
Publication statusPublished - 21 Apr 2003

Keywords

  • 1,3-dipolar cycloadditions
  • Density functional theory
  • Electrophilicity power

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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