Solid-State Photoinitiated Cycloaddition Reaction of 4,4$\prime$-(Ethene-1,2-diyl)bis(pyridinium) Dinitrate: Charge-Density Perspective on Initial Stage of the Reaction

Vologzhanina, A.V.; Aleshin, D.Y.; Volodin, A.D.; Savchenkov, A.V.; Ushakov, I.E.; Korlyukov, A.A.

Авторы: Vologzhanina Anna V., Aleshin Dmitry Yu, Volodin Alexander D., Savchenkov Anton V., Ushakov Ivan E., Korlyukov Alexander A.
Журнал: Crystals
Том: 9
Номер: 12
Год издания: 2019
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Первая страница: 613
DOI: 10.3390/cryst9120613
Аннотация: Solid-state photoinitiated [2 + 2] cycloaddition reaction 2(H2bpe)(NO3)2 → (H4tpcb)(NO3)4 (bpe = 1,2-bis(pyrid-4-yl)ethylene; tpcb = 1,2,3,4-tetrakis(pyrid-4-yl)cyclobutane) was carried out in a single-crystal-to-single-crystal manner. The reaction product was characterized by means of X-ray diffraction and 1H NMR spectroscopy. Only the rctt-isomer of tpcb was found as the reaction product. Intermolecular interactions in a single crystal of (H2bpe)(NO3)2 were studied within the QTAIM approach. Although sum energy of strong and weak hydrogen bonds dominates in total packing energy, contribution of π…π stacking interactions to the packing energy is also prominent. At solid (H2bpe)(NO3)2, stacking of photoreactive H2bpe2+ cations is realized via N…C, C…C and C–H…C bonding, although no four-membered cycles formed by these bond paths was found in molecular graph representation. Reduced density gradient (RDG) surfaces and molecular Voronoi surfaces clearly demonstrate accumulation of charge density between olefin groups prone to take part in photoinitiated cycloaddition reactions. Good correlation between description of hydrogen bonding in terms of QTAIM and Voronoi approaches was demonstrated. The Voronoi approach confirmed that during the photoreaction the system of hydrogen bonds remained almost unchanged.
Добавил в систему: Вологжанина Анна Владимировна

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№	Имя	Описание	Имя файла	Размер	Добавлен
1.	экспертное заключение		Vologzhanina_Crystals.pdf	67,4 КБ	13 января 2020 [VologzhaninaAV]
2.	Полный текст		crystals-09-00613.pdf	2,0 МБ	10 декабря 2019 [VologzhaninaAV]

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Solid-State Photoinitiated Cycloaddition Reaction of 4,4$\prime$-(Ethene-1,2-diyl)bis(pyridinium) Dinitrate: Charge-Density Perspective on Initial Stage of the Reactionстатья

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