Substituent Effect of Nitro Group on Aromaticity of Carbazole Rings

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 π-electron delocalization were calculated to estimate the aromaticity of...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2014-12, Vol.50 (9), p.1244-1251
Main Authors: Radula-Janik, K., Kopka, K., Kupka, T., Ejsmont, K.
Format: Article
Language:English
Subjects:
Analysis
Benzene
Chemistry
Chemistry and Materials Science
Heterocyclic compounds
Nitrogen
Optical properties
Organic Chemistry
Pharmacy
Thiophene
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 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 the carbazole ring system exerts only a slight influence on the benzene ring aromaticity.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-014-1586-0