Artículo
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
Grudova, Mariya V.; Gil, Diego Mauricio
; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail S.; Kletskov, Alexey V.; Frontera, Antonio; Zubkov, Fedor I.
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Fecha de publicación:
27/12/2020
Editorial:
Royal Society of Chemistry
Revista:
New Journal of Chemistry
ISSN:
1144-0546
e-ISSN:
1369-9261
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydrodiepoxybenzo[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-Rbenzenesulfonamides (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.
Palabras clave:
F···O INTERACTIONS
,
X-RAY STRUCTURE
,
HIRSHFELD SURFACES
,
DFT CALCULATIONS
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Identificadores
Colecciones
Articulos(INBIOFAL)
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Citación
Grudova, Mariya V.; Gil, Diego Mauricio; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; et al.; 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; Royal Society of Chemistry; New Journal of Chemistry; 44; 46; 27-12-2020; 20167-20180
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