A condensed-to-atom nucleophilicity index. An application to the director effects on the electrophilic aromatic substitutions

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Abstract

The local nucleophilicity of simple substituted aromatic systems is shown to be described on a quantitative basis by using a condensed-to-atoms nucleophilicity index. This quantity constitutes an extension of the global nucleophilicity descriptor, N introduced for reagents in cycloaddition reactions and other organic molecules [Journal of Organic Chemistry 73 (2008) 4615-4624; Journal of Molecular Structure (THEOCHEM) 865 (2008) 68-72]. The local projection Nk is performed on the basis of the normalization condition of the Fukui functions. It is shown that such a simple index provides useful clues about the director effects of the substituents on the electrophilic aromatic substitution (EAS) reactions of aromatic compounds. A discussion of the general frame of validity for the condensed-to-atoms model is presented.

Original languageEnglish
Pages (from-to)86-91
Number of pages6
JournalJournal of Molecular Structure: THEOCHEM
Volume895
Issue number1-3
DOIs
Publication statusPublished - 15 Feb 2009

Keywords

  • Condensed to atoms nucleophilicity
  • Density functional theory
  • Electrophilic aromatic substitution
  • Electrophilicity
  • Nucleophilicity

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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