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 language | English |
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Pages (from-to) | 86-91 |
Number of pages | 6 |
Journal | Journal of Molecular Structure: THEOCHEM |
Volume | 895 |
Issue number | 1-3 |
DOIs | |
Publication status | Published - 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