6533b863fe1ef96bd12c794d

RESEARCH PRODUCT

Substituent effect of nitro group on aromaticity of carbazole rings

Teobald KupkaKlaudia Radula-janikKrzysztof EjsmontK. Kopka

subject

CarbazoleStereochemistryOrganic ChemistrySubstituentharmonic oscillator model of aromaticityAromaticityaromaticityRing (chemistry)Medicinal chemistrychemistry.chemical_compoundMolecular geometrynucleus-independent chemical shiftchemistryNitroBenzenenitrocarbazolessubstituent effectPyrrole

description

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.

yearjournalcountryeditionlanguage
2014-11-20Chemistry of Heterocyclic Compounds
10.1007/s10593-014-1586-0http://link.springer.com/article/10.1007/s10593-014-1586-0