Abstract
The single crystal X-ray diffraction study of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl) and (4,4′-bipyridin)-1-ium-1-yl(perfluoropyridin-4-yl)amides is performed. In all cases, the N+-N− bond length is less than that of the single Nplanar.-Nplanar. bond, but considerably more than that of the double N=N bond, which indicates a weak involvement of the N− lone pair of the C5NF4N− group in conjugation with pyrazine or bipyridine moieties. Quantum chemical calculations by DFT/(PBE/L1), B3LYP/L1, and RI-MP2/L1 methods provide the geometry of amides similar to the experimental one. Crystals of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl)amide form stacks mainly through F-π interactions. The stacks are joined in 3D architecture by weak C-H…N and C-H…F hydrogen bonds. In the case of (4,4′-bipyridin)-1-ium-1-yl(perfluoropyridin-4-yl)amide crystals, an essential role is played by the π stacking interactions of heteroaromatic rings.
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Original Russian Text Copyright © 2012 by G. I. Borodkin, A. Yu. Vorob’ev, Yu. V. Gatilov
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Translated from Zhurnal Strukturnoi Khimii, Vol. 53, No. 5, pp. 967–972, September–October, 2012.
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Borodkin, G.I., Vorob’ev, A.Y. & Gatilov, Y.V. Molecular and crystal structure of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl) and (4,4′-bipyridin-1-ium-1-yl)(perfluoropyridin-4-yl)amides. J Struct Chem 53, 948–953 (2012). https://doi.org/10.1134/S0022476612050186
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DOI: https://doi.org/10.1134/S0022476612050186