Aromaticity of the naphthalene ring substituted by formyl or nitro and secondary amine groups in peri and para positions has been investigated. HOMA (harmonic oscillator model of aromaticity) index of the naphthalene rings has been used to characterize the aromaticity of the investigated molecules. Ellipticity of C2-C3 (C6-C7) bonds, obtained by means of topological analysis of the electron density, has been used as a measure of the through-resonance effect between the para substituents. Dependence of the HOMA values on the rotation angle of formyl and nitro groups to the aromatic plane for naphthalene-1-carbaldehyde and their derivatives with dimethylamino group in para position has been analyzed. It has been shown that the nitro group has a stronger resonance effect and causes greater decrease of aromaticity than the formyl group only for planar or close to planar conformation. The attractive and repulsive peri interactions have been analyzed by using the QTAIM and NCI methods. Interrelation between the peri and para interactions has been discussed.
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