Reactivity of the carbon-carbon double bond towards nucleophilic additions. A DFT analysis

Luis R. Domingo, Patricia Pérez, Renato Contreras

Research output: Contribution to journalArticle

75 Citations (Scopus)

Abstract

The global and local electrophilicity indexes have been used to characterize the reactivity pattern of the CC double bond towards nucleophilic addition reactions. A wide family of molecules including ketones, esters, anhydrides, nitriles and nitrocompounds containing appropriate substitution on the CC double bond have been classified within an unique scale of reactivity. The predictive capability of the theoretical model is tested against a series of benzylidenemalononitriles and substituted α-nitrostilbenes.

Original languageEnglish
Pages (from-to)6585-6591
Number of pages7
JournalTetrahedron
Volume60
Issue number31
DOIs
Publication statusPublished - 26 Jul 2004

Keywords

  • Density functional theory
  • Electrophilicity power
  • Michael additions

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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