Producción CyT
Artículo
Autoría
Espitia Cogollo, Edeimis
;
Piro, Oscar Enrique
;
ECHEVERRIA, GUSTAVO ALBERTO
;
Tuttolomondo, María Eugenia
;
Perez, Hiram
;
Jios, Jorge Luis
;
ULIC, SONIA ELIZABETH
Fecha
2020
Editorial y Lugar de Edición
ROYAL SOC CHEMISTRY
Revista
NEW JOURNAL OF CHEMISTRY,
vol. 44
(pp. 16006-16019)
ROYAL SOC CHEMISTRY
Resumen
Información suministrada por el agente en
SIGEVA
The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = -H,2: R = -NO2,3: R = -CH3,4: R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol-keto/keto-enol tautomerism on theo-hydroxyacetophenone moiety was analyzed in terms of the synergy between O-H?O intramolecular hydrogen bond ...
The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = -H,2: R = -NO2,3: R = -CH3,4: R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol-keto/keto-enol tautomerism on theo-hydroxyacetophenone moiety was analyzed in terms of the synergy between O-H?O intramolecular hydrogen bond strengthening and the enhancement of ? delocalization within the pseudo ring. The preference of the enol-keto form was attributed to the aromatic stabilization energy. The proton in the triazole ring was located on the intermediate nitrogen atom, with no evidence of prototropy in the studied series. Compounds1and4have similar structural motifs with N-H?O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along thea-axis. For2, it was found that both oxygen atoms of the nitro substituent participate as acceptors, connecting adjacent molecules by hydrogen bonds through the N-H and O-H groups. In compound3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of3, giving rise to a three-dimensional H-bonding network. These intra and intermolecular interactions, which affect the absorption band locations of the involved groups, were also detected in the vibrational spectra of the studied triazoles.
Ver más
Ver menos
Palabras Clave
X-ray crystal structurePixel energiesVibrational SpectroscopyMolecular Interactions
Descargue o solicite el texto completo