ChemistryMedicine

Hossein Fallah-Bagher-Shaidaei, C. Wannere, C. Corminboeuf, R. Puchta, P. Schleyer

2006.2.2ORGANIC LETTERS

DOI: 10.1021/ol0529546

tlooto Summary

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 to find the most fundamentally grounded index, NICS(0)pizz.

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).

Citation format

FALLAH-BAGHER-SHAIDAEI, Hossein, et al. Which NICS aromaticity index for planar pi rings is best? ORGANIC LETTERS, 2006, 8 5: 863–6.