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 Full article
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Journal of Structural Chemistry
ISSN: 0022-4766 , E-ISSN: 1573-8779 |
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| Output data | Year: 2012, Volume: 53, Number: 5, Pages: 948-953 Pages count : 6 DOI: 10.1134/S0022476612050186 | ||||
| Tags | N-imines of bipyridine and pyrazine; C-F-pi interactions; pi stacking; hydrogen bond; single crystal X-ray diffraction study; quantum chemical calculations | ||||
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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 N-planar.-N-planar. 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-pi interactions. The stacks are joined in 3D architecture by weak C-HaEuro broken vertical bar N and C-HaEuro broken vertical bar 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 pi stacking interactions of heteroaromatic rings.
Cite:
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
Journal of Structural Chemistry. 2012. V.53. N5. P.948-953. DOI: 10.1134/S0022476612050186 WOS Scopus РИНЦ
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
Journal of Structural Chemistry. 2012. V.53. N5. P.948-953. DOI: 10.1134/S0022476612050186 WOS Scopus РИНЦ
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
Бородкин Г.И.
, Воробьев А.Ю.
, Гатилов Ю.В.
Молекулярная и кристаллическая структура (пиразиний-1)(перфторпиридин-4-ил) и (4,4′-бипиридилий)-1-ил(перфторпиридин-4-ил) амидов
Журнал структурной химии (J STRUCT CHEM+). 2012. Т.53. №5. С.967-972. РИНЦ
Молекулярная и кристаллическая структура (пиразиний-1)(перфторпиридин-4-ил) и (4,4′-бипиридилий)-1-ил(перфторпиридин-4-ил) амидов
Журнал структурной химии (J STRUCT CHEM+). 2012. Т.53. №5. С.967-972. РИНЦ
Dates:
| Published print: | Sep 1, 2012 |
| Published online: | Dec 2, 2012 |
Identifiers:
| Web of science | WOS:000312214700018 |
| Scopus | 2-s2.0-84874446856 |
| Elibrary | 20484865 |
| OpenAlex | W2059318882 |