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Which NICS Aromaticity Index for Planar π Rings Is Best?

Organic Letters · 2006 · Vol. 8(5) · pp. 863–866

Hossain Fallah‐Bagher‐Shaidaei✉(Friedrich-Alexander-Universität Erlangen-Nürnberg)Chaitanya S. Wannere(Friedrich-Alexander-Universität Erlangen-Nürnberg)Clémence Corminbœuf(University of Georgia)Ralph Puchta(University of Georgia)Paul von Ragué Schleyer(Islamic Azad University Rasht Branch)

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Abstract

Five increasingly sophisticated aromaticity indexes, based on nucleus-independent chemical shifts (NICS), were evaluated against a uniform set of aromatic stabilization energies (ASE) for 75 mono- and polyheterocyclic five-membered rings. While acceptable statistical correlations were given by all of the NICS methods, the most fundamentally grounded index, NICS(0)pizz (based on the pi contribution to the out-of-plane zz tensor component), performed best statistically (cc=0.980) and in practice. The easily computable NICS(1)zz index is a useful alternative (cc=0.968).

Synthesis and Properties of Aromatic Compounds Fullerene Chemistry and Applications Graph theory and applicationsAromaticityChemistryTensor (intrinsic definition)Index (typography)PlanarComputational chemistryPure mathematicsMoleculeOrganic chemistryMathematics

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