4.8 Article

Which NICS aromaticity index for planar π rings is best?

Journal

ORGANIC LETTERS
Volume 8, Issue 5, Pages 863-866

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0529546

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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)(pi zz) (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).

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