Which NICS aromaticity index for planar π rings is best?

被引:1073
作者
Fallah-Bagher-Shaidaei, H
Wannere, CS
Corminboeuf, C
Puchta, R
Schleyer, PV
机构
[1] Islamic Azad Univ, Rasht Branch, Dept Chem, Rasht, Iran
[2] Univ Georgia, Ctr Computat Chem, Dept Chem, Athens, GA 30602 USA
[3] Univ Erlangen Nurnberg, Comp Chem Ctr, D-91052 Erlangen, Germany
关键词
D O I
10.1021/ol0529546
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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).
引用
收藏
页码:863 / 866
页数:4
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