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Journal of Structural Chemistry

2008 year, number 5

X-ray and quantum-topological studies of intermolecular interactions in partially fluorinated quinoline crystals

I. Y. Bagryanskaya, M. A. Grishina, L. Y. Safina, G. A. Selivanova, V. A. Potemkin, Y. V. Gatilov
Keywords: X-ray analysis, quantum-topological analysis, fluorinated quinolines, supramolecular motifs, π-stacking, N…H, F…H, F…F, and C-F…π nonvalent interactions
Pages: 933-941


An X-ray study of the crystals of bicyclic compounds containing fluorinated aromatic and nonfluorinated heteroaromatic rings, 5,6,7,8-tetrafluoroquinoline, 5,6,8-trifluoroquinoline, 5,7-difluoroquinoline, 5,7,8-trifluoro-2-phenylquinoline, and 5,7,8-trifluoro-6-trifluoromethylquinoline, was carried out. The basic supramolecular motifs and the underlying intermolecular interactions that control the lattice structure of these compounds were investigated. B3LYP DFT quantum-chemical calculations (6-311G(d,p) basis set) and the topological analysis of the electron density distribution in terms of Bader's QTAIM theory were performed for the compounds. It is shown that the intermolecular interactions in question, traditionally regarded as nonvalent interactions, are related, to a definite extent, to the formation of very weak covalent chemical bonds in the intermolecular space due to the overlap of the "tails" of the molecular wave functions.