Synthesis, crystal structure and quantum chemical study on 3-phenylamino-4-phenyl-1,2,4-triazole-5-thione

Molecules

Volumn 14, Issue 2, 2009, Pages 608-620

  Wang, Hong Yan ^a   Zhao, Pu Su ^a   Li, Rong Qing ^a   Zhou, Su Min ^a  

^a HUAIYIN NORMAL UNIVERSITY   (China)

Author keywords

Crystal structure; DFT; Second order optical nonlinearity; Synthesis

Indexed keywords

ANTIINFECTIVE AGENT; THIOKETONE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FUNGUS; HYDROGEN BOND; MICROBIOLOGICAL EXAMINATION; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

ANTI-INFECTIVE AGENTS; CRYSTALLOGRAPHY, X-RAY; FUNGI; HYDROGEN BONDING; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; THERMODYNAMICS; THIONES; TRIAZOLES;

EID: 61549126892     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14020608     Document Type: Article

References (35)

1. Xu, L.Z; Jian, F.F.; Qin, Y.Q.; Jiao, K. Structure and Biological Activities of 3-Phenyl-2-[1-benzoyl-1-(1,2,4-trizol-l-yl)] Methenyl Thiazolidine. Chem. Res. Chin. Univ. 2004, 20, 305-307.
2. Genin, M.J.; Allwine, D.A.; Anderson, DJ.; Barbachyn, M.R.; Emmert, D.E.; Garmon, S.A.; Graber, D R.; Grega, K.C.; Hester, J.B.; Hutchinson, D.K.; Morris, J.; Reischer, R.J.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H. Substituent Effects on the Antibacterial Activity of Nitrogen-Carbon-Linked (Azolylphenyl)oxazolidinones with Expanded Activity Against the Fastidious Gram-Negative Organisms Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem. 2000, 43, 953-970.
3. Banting, L.; Nicholls, PJ.; Shaw, M.A.; Smith, H.J. Progress in Medicinal Chemistry; Elsevier Science: Amsterdam, The Netherlands, 1989.
4. Jian, F.F.; Xu, L.Z.; Shi, J.G.; Xiao, H.L. 2-(1,3-Dithiolan-2-ylidene)- 1-phenyl-2-(1,2,4-triazol-1-yl)ethanone. Acta Cryst. 2004, E6s0, o1204-o1205.
5. Jian, F.F; Xiao, H.L; Qin, Y.Q.; Xu, L.Z. 2-Benzoyl-N-phenyl-2-(1,2,4- triazol-1-yl)thioacetamide and 2-(4-methoxybenzoyl)-N-phenyl-2-(1,2,4-triazol-1- yl)thioacetamide. Acta Cryst. 2004, C60, o492-o495.
6. Xu, L.Z.; Jian, F.F.; Gao, H.R.; Zhu, C.Y. Synthesis, Structure and Biological Activities of S-[α (4-Methoxyphenylcarbonyl)-2-(1,2,4- Triazole-1-yl)]ethyl-N, N, dimethyldithiocarbamate. Chin. J. Chem. 2003, 27, 1615-1618.
7. Jian, F.F.; Xu, L.Z.; Li, L.; Zhu, C.Y. Synthesis and crystal structure of compound: 2,2-dimethyl-4-[1H-(1,2,4-triazoly)]-4-[1H-benzotriazolyl]-3- butanone. Chin. J. Struct. Chem. 2004, 23, 539-542.
8. Jian, F.F.; Bai, Z.S.; Xiao, H.L.; Li, K. 3-Benzyl-4-phenyl-lF-l,2,4- triazole-5(477)-thione. Acta Cryst. 2005, E61, o557-o558.
9. 2-1,2,4-triazoline-5-thione. Acta Crystallogr. 1979,555,489-491.
10. Belcher, L.K.A.; Squattrito, P.J. Structure of 4-amino-3-butyl-1,2,4- triazole-5-thione: Relation to derivatives with H, Me, Et, and Pr in the 3-position. J. Chem. Cryst. 2006, 36, 175-180.
11. Heras, M.; Font, D.; Linden, A.; Villalgordo, J.M. Synthesis of Triazolo[1,5-a]triazin-7-one Derivatives and Highly Functionalized [1,2,4]Triazoles. Helv. Chim. Acta. 2003, 86, 3204-3214.
12. II coordination polymers: unusual solvothermal formation of a LiGe-type framework directed by in situ S-S coupling of 5-(4-pyridyl)-1H-1,2,4-triazole-3-thiol. Chem. Commun. 2008, 1296-1298.
13. Koch, W.; Holthausen, M.C.A. A Chemistry Guide to Density Functional Theory; Wiley-VCH: Weinheim, New York, Chichester, 2000.
14. Parr, R.R.; Yang, R.G. Density Functional Theory of Atoms and Molecules. Oxford University Press: New York, USA, 1989, and references therein.
15. Steiner, T. C-H-O Hydrogen Bonding in Crystals. Cryst. Rev. 1996, 6, 1-51.
16. Jeffrey, G.A.; Maluszynska, H.; Mitra, J. Hydrogen bonding in nucleosides and nucleotides. Int. J. Biol. Macromol. 1985, 7, 336-348.
17. Hunter, R.H.; Haueisen, R.H.; Irving, A. The First Water-Dependent Liquid Clathrate: X-Ray Evidence in the Solid for a C-H⋯π (Heteroarene) π⋯H-C Interaction. Angew. Chem. Int. Ed. Engl. 1994, 33, 566-568.
18. 2O (M = Ni, Co). J. Chem. Crystallogr. 2004, 34, 647-652.
19. Vos, G.; de Graaf, R.A.G.; Haasnoot, J.G.; van derKraan, A.M.; de Vaal, P.; Reedijk, J. Crystal structure at 300 and 105 K, magnetic properties and Moessbauer spectra of bis(triaquatris(4-ethyltriazole-N1)iron(II)-N2,N2′, N2″)iron(II) hexakis(trifluoromethanesulfonate). A linear, trinuclear iron(II) compound, showing a unique high-spin-low-spin transition of the central iron atom. Inorg. Chem. 1984, 23, 2905-2910.
20. You, X.Z. Molecular-based Materials -Opto-electronic Functional Compounds, Science and Technology Publishing Company: Shanghai, P.R. China, 2001; p. 164.
21. Jian, F.F.; Zhao, P.S.; Bai, Z.S.; Cai, Z.J. Experimental and Theoretical Study on 4-Phenyl-3-[(1,2,4-triazol-l-yl)methyl]-triazole-5-thione.Polish J. Chem. 2006, 80, 325-333.
22. Xu, L.Z.; Zhai, Z.W.; Yu, G.P.; Qin, Y.Q.; Yang, Y.X. Syntheses and Biological Activities of Novel Benzotriazole Compounds Containing a Thioamide Group. Chem. Res. Chinese U. 2006. 22, 574-576.
23. Sheldrick, G.M. Siemens Analytical X-Ray Systems. In SHELXTL, v5 Reference Manual; Madison: WI, USA, 1997.
24. Wilson, A.J. International Table for X-Ray Crystallography; Kluwer Academic: Dordrecht, The Netherlands, 1992; Vol. C: Tables 6.1.1.4 (pp. 500-502) and 4.2.6.8 (pp. 219-222), respectively.
25. Perdew, J.P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996, 77, 3865-3868.
26. Perdew, J.P.; Burke, K.; Ernzerhof, M. K+ Emission in Symmetric Heavy Ion Reactions at Subthreshold Energies. Phys. Rev. Lett. 1997, 78, 1396-1396.
27. Peng, C.; Ayala, P.Y.; Schlegel, H.B.; Frisch, M.J. Using redundant internal coordinates to optimize equilibrium geometries and transition states. J. Comput. Chem. 1996, 17, 49-56.
28. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A.; Vreven, Jr.T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, DJ.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M. W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez. C.; Pople, J. A. Gaussian; Gaussian Inc.: Wallingford, CT, USA, 2004.
29. Runge, E.; Gross, E.K.U. Density-Functional Theory for Time-Dependent Systems. Phys. Rev. Lett. 1984, 52, 997-1000.
30. Petersilka, M.; Gossmann, U.J.; Gross, E.K.U. Excitation Energies from Time-Dependent Density-Functional Theory. Phys. Rev. Lett. 1966, 76, 1212-1215.
31. Bauernschmitt, R.; Ahlrichs, R. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem. Phys. Lett. 1996, 256, 454-464.
32. Jamorski, C.; Casida, M.E.; Salahub, D.R. Dynamic polarizabilities and excitation spectra from a molecular implementation of time-dependent density-functional response theory: N2 as a case study. J. Chem. Phys. 1996, 104, 5134-5138.
33. Dewar, M.J.S.; Thiel, W. Ground states of molecules. 38. The MNDO method. Approximations and parameters. J. Am. Chem. Soc. 1977, 99, 4899-4907.
34. Stewart, J.J.P. Optimization of parameters for semiempirical methods I. Method. J. Comput. Chem. 1989, 10, 209-220.
35. Stewart, J.J.P. QCPE Program 455, 1983, Version 6.0, 1990.