Artículo
Synthesis and X‐ray characterization of 4,5‐dihydropyrazolyl‐thiazoles bearing a coumarin moiety: on the importance of antiparallel π‐stacking
Madni, Murtaza; Ahmed, Muhammad Naeem; Abbasi, Ghazala; Hameed, Shahid; Ibrahim, Mahmoud A. A.; Tahir, Muhammad N.; Ashfaq, Muhammad; Gil, Diego Mauricio
; Gomila, Rosa M.; Frontera, Antonio
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Fecha de publicación:
09/2022
Editorial:
Wiley-VCH
Revista:
Chemistry Select
ISSN:
2365-6549
e-ISSN:
2365-6549
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The synthetic protocol and solid state characterization of two new coumarin-pyrazolylthiazole hybrids (1-2) are detailed in this manuscript. Synthesized compounds were characterized applying nuclear magnetic resonance, Fourier-transform infrared spectroscopy and single-crystal X-ray diffraction techniques. A detailed structural analysis of 3-(2-(5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1) and 3-(2-(3,5-bis(4-bromophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) is reported along with a detailed description of the noncovalent interactions and their evaluation using Hirshfeld surface analysis, emphasizing the structure-directing role of C−H⋅⋅⋅O, Br⋅⋅⋅π and π–π interactions. Finally, DFT energetics, molecular electrostatic potential (MEP), quantum theory of “atoms-in-molecules” (QTAIM) and noncovalent interaction plot (NCIplot) index computations have been used to further investigate the relative importance of two different π-stacking complexes observed in the solid state of both compounds, which are recurrent binding motifs in their crystal packing.
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Articulos(INBIOFAL)
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Citación
Madni, Murtaza; Ahmed, Muhammad Naeem; Abbasi, Ghazala; Hameed, Shahid; Ibrahim, Mahmoud A. A.; et al.; Synthesis and X‐ray characterization of 4,5‐dihydropyrazolyl‐thiazoles bearing a coumarin moiety: on the importance of antiparallel π‐stacking; Wiley-VCH; Chemistry Select; 7; 36; 9-2022; 1-9
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