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RESEARCH PRODUCT

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

Luis R. DomingoMario Duque-noreñaEduardo ChamorroPatricia Pérez

subject

NucleophileComputational chemistryChemistryElectrophileAtomMoleculeDensity functional theoryPhysical and Theoretical ChemistryElectrophilic aromatic substitutionCondensed Matter PhysicsBiochemistryCycloadditionOrganic molecules

description

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 N k 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.

yearjournalcountryeditionlanguage
2009-02-01Journal of Molecular Structure: THEOCHEM
https://doi.org/10.1016/j.theochem.2008.10.014