RESUMEN
The molecular geometry, vibrational frequencies, and gauge including atomic orbital (GIAO) (1)H and (13)C NMR chemical shift values of the title compound in the ground state have been calculated using the Hartree-Fock (HF) and density functional theory (DFT) methods with 6-31G(d) basis sets, and compared with the experimental data. The calculated results show that the optimized geometries can well reproduce the crystal structural parameters and the theoretical vibrational frequencies, and (1)H and (13)C NMR chemical shift values show good agreement with experimental data. To determine conformational flexibility, molecular energy profile of the title compound was obtained by HF/6-31G(d) and (DFT/B3LYP) calculations with respect to selected degree of torsional freedom, which was varied from -180° to +180° in steps of 10°. The energetic behavior of the title compound in solvent media was examined using the B3LYP method with the 6-31G(d) basis set by applying the Onsager and the polarizable continuum model (PCM). The results obtained with these methods reveal that the PCM method provided more stable structure than Onsager's method. The title compound has been tested in vitro for biological effects.
Asunto(s)
Piridinas/síntesis química , Piridinas/farmacología , Tiadiazoles/síntesis química , Tiadiazoles/farmacología , Antiinfecciosos/síntesis química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Compuestos de Bifenilo/química , Cristalografía por Rayos X , Depuradores de Radicales Libres/farmacología , Enlace de Hidrógeno , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Picratos/química , Piridinas/química , Solventes/química , Electricidad Estática , Termodinámica , Tiadiazoles/química , Torsión Mecánica , VibraciónRESUMEN
The title molecule, 4-allyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione (C(10)H(10)N(4)S), was synthesized and characterized by IR-NMR spectroscopy and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group is P2(1)/c, a=8.006(5)Å, b=15.363(5)Å, c=8.936(5)Å, ß=104.441(5)° and V=1064.4(10)Å(3), F(000)=456, D(x)=1.362 g/cm(3). In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies, gauge including atomic orbital (GIAO) (1)H and (13)C chemical shift values of the title compound in the ground state have been calculated using the Hartree-Fock (HF) and density functional method (DFT/B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of the title compound was obtained by HF/6-31G(d) and (DFT/B3LYP) calculations with respect to selected degree of torsional freedom, which was varied from -180° to +180° in steps of 10°. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO), and several thermodynamic properties were performed by the HF and DFT methods.
Asunto(s)
Tionas/química , Triazoles/química , Cristalografía por Rayos X , Espectroscopía de Resonancia Magnética , Modelos Moleculares , Piridinas/síntesis química , Piridinas/química , Espectrofotometría Infrarroja , Electricidad Estática , Tionas/síntesis química , Triazoles/síntesis químicaRESUMEN
The title compound, C(14)H(9)N(5)S, has been synthesized and characterized both spectroscopically and structurally. The triazolo-thiadiazole system, the pyridine ring and the phenyl ring are all planar. The plane of the triazolo-thiadiazole system forms dihedral angles of 1.53 (13) and 7.55 (12) degrees with the planes of the pyridine and phenyl rings, respectively. In the molecule, there are two intramolecular interactions of types C-H...N and C-H...S. Intermolecular C-H...N interactions involving a phenyl CH group and a triazole N atom lead to the formation of a one-dimensional chain. In the crystal structure, two types of pi-pi interactions affect the packing of the molecules. In addition, there are intermolecular non-bonded S...N contacts of 2.870 (2) A, which may cause steric hindrance.