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Synthesis, X-ray characterization and theoretical study of 3a,6:7,9a-diepoxybenzo[de]isoquinoline derivatives: on the importance of F···O interactionsстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 20 января 2021 г.
- Авторы: Grudova Mariya V., Gil Diego Mauricio, Khrustalev Victor N., Nikitina Eugeniya V., Sinelshchikova Anna A., Grigoriev Mikhail, Kletskov Alexey V., Frontera Antonio, Zubkov Fedor Ivanovich
- Журнал: New Journal of Chemistry
- Том: 44
- Год издания: 2020
- Издательство: Royal Society of Chemistry
- Местоположение издательства: United Kingdom
- Первая страница: 20167
- Последняя страница: 20180
- DOI: 10.1039/d0nj04328a
- Аннотация: The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydro-diepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-R-benzenesulfonamides (bis-dienes, R = Me, F, Cl, Br, I) are reported in this manuscript. The implementation of kinetic/thermodynamic control allowed to obtain both “pincer”- and “domino”-types adducts in good/moderate yields. In the solid state, most of the pincer adducts form self-assembled dimers (R = Me, Cl, Br, I) and, contrariwise, the domino adducts form 1D supramolecular chains, which are described in detail herein. Remarkably, in the self-assembled dimers, bifurcated halogen bonds involving one fluorine atom of the CF3 group and both O-atoms of sulfonamide are formed, which have been analyzed using DFT calculations, QTAIM and NCIplot computational tools.
- Добавил в систему: Астахов Григорий Сергеевич