Synthesis, characterization and DFT study of a new family of pyrazole derivatives
Autor
Faundez-Gutierrez R.
Macleod-Carey D.
Zarate X.
Bustos C.
Molins E.
Schott E.
Resumen
This work deals about the synthesis and characterization of compounds containing the pyrazole core belonging to the family of (E)-4-((3,5-dimethyl-1- (4-R-phenyl)-1H-pyrazol-4-yl)diazenyl)benzonitrile, with possible application as ligands in inorganic chemistry. These compounds were obtained by reaction of a substituted arylhydrazine, RC6H4NHNH2, R: 4-OCH3, 4-CH3, 4-F, 4-H, 4-Cl, 4-CF3, 4-CN, 3-Cl, 3-NO2, 2-Cl and perfluorophenylhydrazine, C6F 5-NH2NH; with a β-diketohydrazone precursor of formula (CH3CO)2CNNHC6H44-CN. Analytical techniques (MP and EA) and spectroscopic methods such as UV-Vis, IR, 1H NMR, 13C NMR were employed to characterize the prepared systems. One of the synthesized compounds yielded in ethanol single crystals suitable for X-ray diffraction study. In order to model all the studied compounds and the molecular orbitals involved in the transitions, DFT and TDDFT calculations were performed. The non-variability of the bond distances suggests the robustness of the conjugated structure formed by the RC6H 4pyrazoleNNbenzonitrile rings, which is poorly affected by the change of the substituents over the phenyl ring. © 2014 Elsevier Ltd. All rights reserved.
Colecciones
Ítems relacionados
Mostrando ítems relacionados por Título, autor o materia.
-
Article
Tuning the molecular/electronic structure of new substituted pyrazoles: Synthesis, biological trials, theoretical approaches and Hammett correlations (2020)
Bustos C.; Alvarez-Thon L.; Molins E.; Moreno-Villoslada I.; Vallejos-Contreras G.; Sánchez C.; Zarate X.; Mac-Leod Carey D.; Schott E. (Elsevier B.V., 2018) -
Article
Design, characterization and quantum chemical computations of a novel series of pyrazoles derivatives with potential anti-proinflammatory response (2020)
Burboa-Schettino P.; Bustos C.; Molins E.; Figueroa X.F.; Llanquinao J.; Zarate X.; Vallejos G.; Diaz-Uribe C.; Vallejo W.; Schott E. (Elsevier B.V., 2020) -
Article
A novel series of pyrazole derivatives toward biological applications: experimental and conceptual DFT characterization (2021)
Ortiz, Pedro D.; Castillo-Rodriguez, Judith; Tapia, Jorge; Zárate, Ximena P.; Vallejos, Gabriel A.; Roa, Vanesa; Molins, Elies; Bustos, Carlos J.; Schott V, Eduardo (Springer Science and Business Media Deutschland GmbH, 2021)Abstract: A new series of 13 pyrazole-derivative compounds with potential antifungal activity were synthetized with good yields. The series have the (E)-2-((1-(R)-3,5-dimethyl-1H-pyrazol-4-yl)diazenyl)phenol general structure ...