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SUBSTITUENT EFFECT OF NITRO GROUP ON AROMATICITY OF CARBAZOLE RINGS

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


Keywords


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

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