Substituent Effect of Nitro Group on Aromaticity of Carbazole Rings | Health & Environmental Research Online (HERO)

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HERO ID

4283731

Reference Type

Journal Article

Title

Substituent Effect of Nitro Group on Aromaticity of Carbazole Rings

Author(s)

Radula-Janik, K; Kopka, K; Kupka, T; Ejsmont, K

Year

2014

Is Peer Reviewed?

Yes

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122
EISSN: 1573-8353

Volume

Issue

Page Numbers

1244-1251

Language

English

DOI

10.1007/s10593-014-1586-0

Web of Science Id

WOS:000346168700003

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84922102314&doi=10.1007%2fs10593-014-1586-0&partnerID=40&md5=3ea5b7450d67ee4a9ff48bc4c09f1212
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Abstract

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.

Keywords

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