Solvents Effect on 4-Phenyl-5-(2-Thienyl)-2,4-Dihydro-3H-1,2,4-Triazol-3-Thion Molecule: Experimental And Theoretical Study

Year 2023, Volume: 6 Issue: 1, 57 - 64, 21.06.2023

M.mürşit Temüz , Pelin Koparır , Mehmet Yıldırım

https://doi.org/10.54565/jphcfum.1285639

Abstract

In this study 4-phenyl-5-(2-thienyl)-2, 4-dihydro-3H-1,2,4-triazol-3-thion was synthesized using experimental method and later characterized using spectroscopic methods. The titled molecule is then designed, optimized and charaterized with theoretical first principle method. The result compared and the titled molecule is solvated with polar and non-polar solvent to see the effect of their interaction and changes that occurs in the spectroscopic results.

Keywords

DFT, Homo, Lumo, Hatree-Fock, Optimization, Solvents Effect

References

• [1] V. Padmavathi, P. Thriveni, G. Sudhakar Reddy, D. Deepti, Synthesis and antimicrobial activity of novel sulfone-linked bis heterocycles, Eur. J. Med. Chem. 43 (5) (2008) 917-924.
• [2] M. Amir, H. Kumar, S.A. Javed, Eur. Condensed bridgehead nitrogen heterocyclic system: Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid, J. Med. Chem. 43 (10) (2008) 2056-2066.
• [3] K. Sztanke, T. Tuzimski, J. Rzymowska, K. Pasternak, M. Kandefer-Szerszen, Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives, Eur. J. Med. Chem. 43 (2) (2008) 404-419.
• [4] C. Kus ̧ G.A. Kılcıgil, S. Özbey, F.B. Kaynak, M. Kaya, T. Çoban, B.C. Eke, Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class, Bioorg. Med. Chem. 16 (8) (2008) 4294-4303.
• [5] A.M. Isloor, B. Kalluraya, M. Rao, A.M. Rahiman, Synthesis and anti-inflammatory evaluation of some new 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles bearing pyrazole moiety, J. Saudi Chem. Soc. 4 (2000) 265-270.
• [6] B. Kalluraya, A.M. Isloor, S. Shenoy, Synthesis and biological activity of 6-substituted-3-[4-(3-substituted pyrazolidene) hydrazino-4-thiazolyl] coumarins, Indian J. Heterocycl. Chem. 11 (2001) 159-162.
• [7] B. Kalluraya, A.M. Isloor, F.V. Priya, R.L. Jagadeesha, Synthesis and pharmacological activity of some-4-(substituted)-2-4-arylhydrazono-3-methyl-5-oxo-2-pyrazolin-1-yl] thiazoles, Indian J. Heterocycl. Chem. 13 (3) (2004) 245-248.
• [8] M.S. Karthikeyan, D.J. Prasad, B. Poojary, K.S. Bhat, B.S. Holla, N.S. Kumari, Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety, Bioorg. Med. Chem. 14 (22) (2006) 7482-7489.
• [9] D. Satyanarayana, B. Kalluraya, N. George, Studies on the synthesis and biological activity of 3-arylaminomethyl-5-(3-pyridyl)- 1,3,4-oxadiazole-2-thione derivatives, J. Saudi Chem. Soc. 6 (3) (2002) 459-464.
• [10] L. Ying, Y.Z. Shun, Z. Hong, B.J. Cao, F.D. Wang, Y. Zhang, Y.L. Shi, J. Yang, B.A. Wu, Artemisinin derivatives bearing Mannich base group: synthesis and antimalarial activity, Bioorg. Med. Chem. 11 (20) (2003) 4363-4368.
• [11] R.J. Vishnu, L. Mishra, H.N. Pandey, A.J. Vlietinck, Synthesis and Biological Activities of Some Novel Aminomethyl Derivatives, J. Heterocycl. Chem. 23 (5) (1986) 1367-1369.
• [12] B. Kalluraya, A.M. Isloor, R.M. Chimbalkar, S. Shenoy, Synthesis and biological activity of some Mannich bases, Indian J. Heterocycl. Chem. 10 (2001) 239-240.
• [13] B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles, Eur. J. Med. Chem. 38 (2003) 759-767.
• [14] A. Cansiz, S. Servi, M. Koparir, M. Altintas, M. Digrak, Synthesis and Biological Activities of Some Mannich Bases of 5-(2-furyl)- 1,2,4-triazole-3-thiones, J. Chem. Soc. Pakistan. 23 (2001) 237-240.
• [15] S.O. Yildirim, M. Akkurt, M. Koparir, A. Cansiz, M. Sekerci, F.W. Heinemann, 3-(2-furyl)-4-(4-methoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione, Acta Crystallogr. E 60 (2004) 2368-2370.
• [16] O.F. Ozturk, A. Cansiz, M. Koparir, Transit. Preparation and characterization of Co(II), Ni(II) and Cu(II) complexes of a ligand containing 1,3,4-thiadiazole groups, Metal Chem. 32 (2007) 224-227.
• [17] S. Ozturk, M. Akkurt, A. Cansiz, M. Koparir, M. Sekerci, F.W. Heinemann, . 2-Amino-5-phenyl-1,3,4-thiadiazole at 110 K, Acta Crystallogr. E 60 (2004) 820-821.
• [18] M. Dincer, N. Ozdemir, A. Cetin, A. Cansiz, O. Buyukgungor, 6-Phenyl-3-(4-pyridyl)-1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazole, Acta Crystallogr. C 60 (2005) 665-667.
• [19] S. Ozturk, M. Akkurt, A. Cansiz, M. Koparir, M. Sekerci, F.W. Heinemann, 3-Benzyl-4-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione, Acta Crystallogr. E 60 (2004) 642-644.