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

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 Научная публикация

Журнал

Journal of Structural Chemistry
ISSN: 0022-4766 , E-ISSN: 1573-8779

Вых. Данные

Год: 2012, Том: 53, Номер: 5, Страницы: 948-953 Страниц : 6 DOI: 10.1134/S0022476612050186

Ключевые слова

N-imines of bipyridine and pyrazine; C-F-pi interactions; pi stacking; hydrogen bond; single crystal X-ray diffraction study; quantum chemical calculations

Авторы

Borodkin G.I. ^1,2 , Vorob'ev A.Yu. ^1,2 , Gatilov Yu.V. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Div, NN Vorozhtsov Inst Organ Chem, Novosibirsk, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk, Russia

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.

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

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

Опубликована в печати:	1 сент. 2012 г.
Опубликована online:	2 дек. 2012 г.

Web of science	WOS:000312214700018
Scopus	2-s2.0-84874446856
РИНЦ	20484865
OpenAlex	W2059318882