Synthesis and Theoretical Characterization of 4-(p-tollyl)-5-(thiophen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione Using Experimental and Quantum Chemical Calculations.

Year 2022, , 7 - 13, 27.06.2022

Kamuran Saraç

https://doi.org/10.17678/beuscitech.1062331

Abstract

The aim of the study was to synthesize 4- (p-tollyl) -5- (thiophene-2-yl) -2,4-dihydro-3H-1,2,4-triazole-3-thione and detect its experimental and the quantum chemical properties. 4-(p-tollil)-5-(tiyofen-2-il)-2,4-dihidro-3H-1,2,4-triazol-3-tiyon was synthesized using by the nucleophilic sübstitüsyon reaction. The synthesized title compound has been characterized both experimentally and theoretically using quantum chemical calculations and spectral techniques. The molecular geometry, vibrational frequencies, and 1H and 13C NMR chemical shifts of the title compound in the ground state were calculated using the density functional method (B3LYP) with the 6–311G(d, p) basis set. It was seen that the calculated infrared and nuclear magnetic resonance values were compatible with the experimental values. To determine conformational flexibility, the molecular energy profile of 4- (p-tollyl) -5- (thiophene-2-yl) -2,4-dihydro-3H-1,2,4-triazole-3-thione was obtained by DFT calculations with respect to the selected torsion angle, which was varied from 180°to +180°in steps of 20°. In addition, the HOMO- LUMO energies of this conformational structure were calculated.

Keywords

4-(p-tolly)-5-(thiophen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, DFT, NMR, IR Spectroscopy

References

• Guan, L. P., Jin, Q. H., Tian, G. R., Chai, K. Y., Quan, Z.S.2007. Synthesis of some quinoline-2 (1H)-one and 1, 2, 4-triazolo [4, 3a] quinolin derivatives as potent anticonvulsants. J Pharm Pharm Sci, 10 (3): 254-62.
• Gujjar, R., Marwaha, A., El Mazouni, F., White, J., White, K.L.,Creason, S.,Phillips, M. A. 2009. Identification of a metabolically Stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice. Journal of medicinal chemistry, 52(7): 1864-1872.
• Mohammad, Y., Fazili, K. M., Bhat, K. A., Ara, T. 2017. Synthesis and biological evaluation of novel 3-O-tethered triazoles of diosgenin as potent antiproliferative agents. Steroids, 118, 1-8.
• Huang, M., Deng, Z., Tian, J., Liu, T. 2017. Synthesis and biological evaluation of salinomycin triazole analogues anticancer agents. European journal of medicinal chemistry, 127, 900-908.
• Lee, T., Cho, M., Ko, S.Y., Youn, H. J., Baek, D. J., Cho, W. J., Kim, S.2007. Synthesis and evaluation of 1, 2, 3-triazole containing analogues of the immunostimulant α-GalCer. Journal of medicinal chemistry, 50(3): 585-589.
• Wang, G., Peng, Z., Wang, J., Li, X., Li, J. 2017. Synthesis, in vitro evaluation and molecular docking studies of novel riazine-triazole derivatives as potential α-glucosidase inhibitors. European journal of medicinal chemistry, 125, 423-429.
• Beutler, E. 1992. Cladribine (2-chlorodeoxyadenosine). The Lancet, 340 (8825): 952-956.
• Kumar, G.S., Prasad, Y.R., Chandrashekar, S.M. 2013. Synthesis and pharmacological evaluation of novel 4-opylthiazole-4-phenyl-1, 2, 4-triazole derivatives as potential antimicrobial and antitubercular agents. Medicinal Chemistry Rearch, 22(2): 938-948.
• Tanak, H. 2011. DFT computational modeling studies on 4-(2, 3-Dihydroxybenzylideneamino)-3-methyl-1H-1, 2, 4-triazol-5 (4H)-one. Computational And Theoretical Chemistry, 967(1): 93-101.
• Becke, A D. 1988. Density-functional exchange-energyapproximation with correct asymptotic behavior. Physical review A,38(6): 3098-3100.
• Beck, A. D. 1993:. Density-functional thermochemistry. III. Theroof exact exchange. J. Chem. Phys, 98(7), 5648-5660
• Lee, C., Yang, W., & Parr, R. G. 1988. Development of the Colle Salvetti correlation-energy formula into a functional of the electron density. Physical review B, 37(2): 785-790
• Merrick, J. P., Moran, D., Radom, L. 2007. An evaluation of harmonic vibrational frequency scale factors. The Journal of Physical Chemistry A, 111(45):11683-11700.
• Dodds, J. L., McWeeny, R., & Sadlej, A. J. 1977. Self-consistent perturbation theory: Generalization for perturbation-dependent non orthogonal basis set. Molecular Physics, 34(6): 1779-1791.
• Öztürk, E., Irak, Z. T., Gümüş, S. 2019. (E)-2-((Fenilimino) metil) Fenol Molekülünün Teorik Olarak İncelenmesi. Journal of the Institute of Science and Technology, 9(1): 407-414.
• Bellamy, L. J. 1980. Associated XH Frequencies, The Hydrogen Bond. In The Infrared Spectra of Complex Molecules. Springer, Dordrecht. 240-292.
• Shahhosseini, L., Nateghi, M. R., SheikhSivandi, S. 2016. Electrochemical synthesis of polymer based on 4-(2-thienyl) benzenamine in aqueous solutions: Electrochemical properties, characterization and application. Synthetic Metals, 211, 66-74.
• McNaught, A. D. 1997. Compendium of chemical terminology Oxford: Blackwell Science. 1669-1971.
• Sakarya, H. 2015. Experimental and theoretical studies of FT-IR,FT-Raman and NMR calculations of 2, 2 ethylenedianiline molecule with the help of density function theory. Master Thesis Ahi Evran University, Institute of Science and Technology.Kırşehir.1-115