Substituent Effect of Nitro Group on Aromaticity of Carbazole Rings

被引：5

作者：

Radula-Janik, K. ^{[1
]}

Kopka, K. ^{[1
]}

Kupka, T. ^{[1
]}

Ejsmont, K. ^{[1
]}

机构：

[1] Univ Opole, PL-45052 Opole, Poland

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2014年 / 50卷 / 09期

关键词：

nitrocarbazoles; aromaticity; harmonic oscillator model of aromaticity; nucleus-independent chemical shift; substituent effect; PI-ELECTRON DELOCALIZATION; LIGHT-EMITTING-DIODES; INDEPENDENT CHEMICAL-SHIFTS; LOCAL AROMATICITY; NEURAL-NETWORKS; DERIVATIVES; ENERGY; DENSITY; SYSTEMS; DENDRIMERS;

D O I：

10.1007/s10593-014-1586-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The molecular geometries of carbazole and its 17 nitro derivatives were optimized at the B3LYP/6-311++G(2d,2p) level of theory. The harmonic oscillator model of aromaticity and nucleus-independent chemical shift descriptors of pi-electron delocalization were calculated to estimate the aromaticity of the carbazole five- and six-membered rings. The biggest changes in the value of both descriptors were observed for the pyrrole ring. The nitro group attached to 3 and/or 6 positions of the carbazole ring system exerts only a slight influence on the benzene ring aromaticity.

引用

页码：1244 / 1251

页数：8

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