Synthesis, X-ray characterization and theoretical study of 3: A,6:7,9 a-diepoxybenzo [de] isoquinoline derivatives: On the importance of F⋯O interactions

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-CC-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 us to obtain both "pincer"- A nd "domino"-type 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, and the QTAIM and NCIplot computational tools. This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Authors
Grudova M.V. 1 , Gil D.M.2 , Khrustalev V.N. 1, 3 , Nikitina E.V. 1 , Sinelshchikova A.A.4 , Grigoriev M.S.4 , Kletskov A.V. 1 , Frontera A.5 , Zubkov F.I. 1
Publisher
Royal Society of Chemistry
Number of issue
46
Language
English
Pages
20167-20180
Status
Published
Volume
44
Year
2020
Organizations
  • 1 Faculty of Science, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 2 Inbiofal (CONICET-UNT), Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, San Miguel de Tucumán, T4000INI, Argentina
  • 3 N. D. Zelinsky Institute of Organic Chemistry of Ras 47 Leninsky Prospect, Moscow, 119991, Russian Federation
  • 4 Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow, 119071, Russian Federation
  • 5 Department of Chemistry, Universitat de les Illes Balears, Crta. de Valldemossa km 7.7, Palma de Mallorca (Baleares), 07122, Spain
Keywords
Sulfur compounds; Surface analysis; Computational tools; DFT calculation; Fluorine atoms; Halogen bonds; Hirshfeld surfaces; Supramolecular chains; Theoretical study; X-ray characterization; X rays
Date of creation
20.04.2021
Date of change
20.04.2021
Short link
https://repository.rudn.ru/en/records/article/record/72435/
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