SUBSTITUENT EFFECT OF NITRO GROUP ON AROMATICITY OF CARBAZOLE RINGS

Authors

  • K. Radula-Janik University of Opole, Faculty of Chemistry
  • K. Kopka University of Opole, Faculty of Chemistry
  • T. Kupka University of Opole, Faculty of Chemistry
  • K. Ejsmont University of Opole, Faculty of Chemistry

DOI:

https://doi.org/10.1007/1596

Keywords:

nitrocarbazoles, substituent effect, aromaticity, harmonic oscillator model of aromaticity, nucleus-independent chemical shift

Abstract

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 π-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 carbazole ring system exerts only slight influence on the benzene ring aromaticity.

How to Cite
Radula-Janik, K.; Kopka, K.; Kupka, T.; Ejsmont, K. Chem. Heterocycl. Compd. 2014, 50, 1244. [Khim. Geterotsikl. Soedin. 2014, 1350.]

For this article in the English edition see DOI 10.1007/s10593-014-1586-0

Author Biographies

K. Radula-Janik, University of Opole, Faculty of Chemistry

Klaudia Radula-Janik

Faculty of Chemistry

K. Kopka, University of Opole, Faculty of Chemistry

Katarzyna Kopka

Faculty of Chemistry

T. Kupka, University of Opole, Faculty of Chemistry

Teobald Kupka

Faculty of Chemistry

K. Ejsmont, University of Opole, Faculty of Chemistry

Krzysztof Ejsmont

Faculty of Chemistry

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Published

2014-09-25

Issue

No. 9 (2014)

Section

Original Papers