Relationship between superelectrophilicity and the electrophilicity index of isolated species

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15 Citations (Scopus)

Abstract

We report a relationship between the superelectrophilicity of a series of dications and the electrophilicity index of isolated species. The enhanced electrophilicity is described by global and local reactivity indexes. Alkyloxonium and carboxonium dications and diprotonated carboxylic acids have been used as simple benchmark systems to discuss this relationship on a qualitative and quantitative basis. The theoretical scale of electrophilicity roughly reproduces the experimental superelectrophilicity hierarchy established on the basis of the 17O and 13C NMR chemical shifts in alkyloxonium and carboxonium ions and diprotonated carboxylic acids.

Original languageEnglish
Pages (from-to)5048-5053
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number15
DOIs
Publication statusPublished - 23 Jul 2004

ASJC Scopus subject areas

  • Organic Chemistry

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