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Which NICS Aromaticity Index for Planar π Rings Is Best?

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Department of Chemistry, Islamic Azad University-Rasht Branch, P.O. Box 41335-3516, Rasht, Iran, Department of Chemistry, Center for Computational Chemistry, University of Georgia, Athens, Georgia 30602-2556, and Computer Chemistry Center, University of Erlangen-Nuremberg, Nägelsbachstr. 25, D-91052 Erlangen, Germany
Cite this: Org. Lett. 2006, 8, 5, 863–866
Publication Date (Web):February 2, 2006
https://doi.org/10.1021/ol0529546
Copyright © 2006 American Chemical Society
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Abstract

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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)πzz (based on the π 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).

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

 Islamic Azad University-Rasht Branch.

 University of Georgia.

§

 University of Erlangen-Nuremberg.

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Complete ref 28. Data for mono- and polyhetero five-membered heterocycles (Tables S1−S4). NICS vs ASE plots for the NICS indexes at other distances (Figure S2) and for only the most aromatic molecules (Figures S3−S6). Plots of the other NICS indexes vs NICS(0)πzz (Figures S7−S10). Glossary of terms. Manual for evaluating dissected NICS. This material is available free of charge via the Internet at http://pubs.acs.org.

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