Vibrational, geometrical and HOMO/LUMO/MEP analyses by using DFT/B3LYP and DFT/M06-2X methods: 3-Amino-1,2,4-triazole

Abstract

The theoretically calculated modes and optimized structure parameters of 3-amino-1,2,4-triazole have been computed with Density Functional Theory (for two important methods) by using 6-311++G(d,p) basis level. We have calculated all data by using Gaussian 09W. The theoretical structure values and vibrational frequencies of investigated compound have been found to be consistent with the experimental values. It was concluded that the optimized molecular geometric parameters (bond lengths and bond angles) and theoretical frequencies are slightly deviated from the experimental values. Because, in theoretical calculations we have assumed that isolated molecule is in gas phase. But in experiments in fact, molecule is solid phase. So, inter- and intra-molecular interactions have been isolated from real situation. In summary, this study will provide support in future spectroscopic and other related studies.

Keywords

• Triazole
• IR
• Vibration
• DFT

DFT/B3LYP ve DFT/M06-2X metotları ile titreşimsel, geometriksel ve HOMO/LUMO/MEP analizleri: 3-Amino-1,2,4-triazole

Abstract

3-amino-1,2,4-triazole molekülünün teorik olarak hesaplanmış modları ve optimize yapı parametreleri (bağ uzunlukları ve bağ açıları) DFT-Yoğunluk Fonksiyon Teorisi (2 önemli metot için) 6-311++G(d,p) baz setini kullanarak hesaplandı. Tüm verilerimizi Gaussian 09W programını kullanarak hesapladık. İncelenen bileşiğin titreşimsel frekans ve teorik yapı değerlerinin deneysel değerlerle tutarlı sonuçlar verdiği gözlendi. Optimize geometrik parametrelerin (bağ uzunlukları ve bağ açıları) ve hesaplanmış frenkansların deneysel değerlerden biraz saptığını sonucuna varabiliriz. Çünkü teorik hesaplamalarda, gaz fazında izole bir molekül olduğunu farz ederiz. Fakat deneylerde gerçekte molekül katı fazdadır. Bu nedenle iç ve moleküller arası etkileşmeler gerçek durumdan izoledir. Özet olarak, bu çalışma gelecekteki spektroskopi ve diğer ilgili çalışmalara destek sağlayacaktır.

Keywords

• Triazol
• IR
• Titreşim
• DFT

References

1. Jones DH, Slack R, Squires S, Wooldridge KRH. “Antiviral chemotherapy. I. The activity of pyridine and quinoline derivatives against neurovaccinia in mice”. Jornal of Medicinal Chemistry, 8(5), 676-680, 1965.
2. Sugden JK, Yoloye TO. “Medicinal applications of indole derivatives”. Pharmaceutica Acta Helvetiae, 53, 65-92, 1978.
3. Stillings MR, Welbourn AP, Walter DS. “Substituted 1,3,4-thiadiazoles with anticonvulsant activity. 2. Aminoalkyl derivatives”. Jornal of Medicinal Chemistry, 29, 2280-2284, 1986.
4. Ilango K, Valentina P. “Synthesis and biological activities of novel 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles”. Der Pharma Chemica, 2, 16-22, 2010.
5. Kane JM, Dudley MW, Sorensen SM, Miller F.P. “2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents”. Jornal of Medicinal Chemistry, 31, 1253-1258, 1988.
6. Gökce H, Oztürk N, Ceylan Ü, Alparslan YB, Alparslan G. “Thiol-thione tautomeric analysis, spectroscopic (FT-IR, Laser-Raman, NMR and UV-vis) properties and DFT computations of 5-(3-pyridyl)-4H-1,2,4-triazole-3-thiol molecule”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 163, 170-180, 2016.
7. Ivan Hameed RT, Ali Hussein RA, Ziad Hussein J A, Dhafir TAA. “Novel bent-core mesogenic of 4-amino-triazole derivatives: synthesis, characterization and liquid crystalline study”. Tetrahedron, 72(29), 4390-4399, 2016.
8. Rauhut G, Pulay P. “Transferable scaling factors for density functional derived vibrational force fields”. Journal of Physical Chemistry, 99, 3093-3100, 1995.

9. Frish A, Nielsen AB, Holder AJ, Gauss View User Manual, Gaussian Inc., Pittsburg, PA, 2001.
10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi, Scalmani MG, Rega N,Petersson GA, 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 JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski J.W, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S,Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision D.01, Gaussian Inc., Wallingford, 2004.
11. Young DC, Computional Chemistry: A Pratical Guide for Applying Techniques to Real-World Problems, New York, USA, John Wiley& Sons Inc., 2001.
12. James WH, Buchanan EG, Müller CW, Dean JC, Kosenkov D, Slipchenko LV, Guo L, Reidenbach AG, Gellman SH, Zwier TS. “Evolution of amide stacking in larger γ-peptides: triamide h-bonded cycles”. Journal of Physical Chemistry A, 115, 13783-13798, 2011.
13. Starova GL, Frank-Kamenetskaya OV, Shibanova EF, Lopyrev VA, Voronkov MG, Makarskii VV. Journal Chemsitryof Heterocyclic Compound, 15, 1149-1150, 1979, Translated from Khim. Geterotsikl, Soedin 10, 1422, 1979.
14. Xavier RJ, Gobinath E. “FT-IR, FT-Raman, ab initio and DFT studies, HOMO-LUMO and NBO analysis of 3-amino-5-mercapto-1,2,4-triazole”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 86, 242-251, 2012.
15. Jamróz MH. Vibrational Energy Distribution Analysis VEDA 4, Warsaw, 2004.
16. Jamróz MH. “Vibrational energy distribution analysis (VEDA): scopes and limitations”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 114(10), 220-230, 2013.
17. http://www.sigmaaldrich.com/analyticalchromatography.html. (25.03.2016)
18. Romano E, Soria NAJ, Rudyk R, Brandan S.A. “Theoretical study of the infrared spectrum of 5-phenyl-1,3,4-oxadiazole-2-thiol by using DFT calculations”. Molecular Simulation 38(7), 561-566, 2012.
19. Ridha SMA, Saleh ZA, Askar FW. “Theoretical and experimental study for FT-IR and UV/VIS spectra of 1,4-diphenyl-3-(phenylammonio)-1H-1,2,4-triazolium (inner salt) by using DFT approach”. Physical Chemistry 5(1), 6-15, 2015.
20. Sathyanarayana DN. Vibrational Spectroscopy: Theory and Application. 1st ed. New Delhi, Indian, New Age International Publishers, 2004.
21. Socrates G. Infrared and Raman Characteristic Group Frequencies, Tables and Charts. 3rd ed. Chichester, USA, Wiley, 2001.
22. Kavitha E, Sundaraganesan N, Sebastian S, Kurt M. “Molecular structure, anharmonic vibrational frequencies and NBO analysis of naphthalene acetic acid by density functional theory calculations”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 77(3), 612-619, 2010.
23. Chaitanya K. “Molecular structure, vibrational spectroscopic (FT-IR, FT-Raman), UV-vis spectra, first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis, thermodynamic properties of benzophenone 2,4-dicarboxylic acid by ab initio HF and density functional method”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 86(2), 159-173, 2012.
24. Kavitha E, Sundaraganesan N, Sebastian S. “Molecular structure, vibrational spectroscopic and HOMO, LUMO studies of 4-nitroaniline by density functional method”. Indian Journal of Pure & Applied Physics (IJPAP), 48(1), 20-30, 2010.
25. Jayaprakash A, Arjunan V, Mohan S. “Vibrational spectroscopic, electronic and quantum chemical investigations on 2,3-hexadiene”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 81(1), 620-630, 2011.
26. Govindarajan M, Karabacak M, Suvitha A, Periandy S. “FT-IR, FT-Raman, ab initio, HF and DFT studies, NBO, HOMO-LUMO and electronic structure calculations on 4-chloro-3-nitrotoluene”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 89(4), 137-148, 2012.
27. War JA, Resmi KS, Sheena M. Y, Panicker CY, Srivastava SK, Makwane S. “Experimental IR, Laser-Raman Spectra and Quantum Chemical Calculations of Corrosion Inhibitor 2-Amino-5-Ethyl-1,3,4- Thiadiazole”. Structural Chemistry-Crystallography Communication, 1(1:6), 1-13, 2015.
28. Panicker CY,Varghese HT, Manjula PS, Sarojini BK, Narayana B, War JA, Srivastava SK, Alsenoy CV, Al-Saadi AA. ‘FT-IR, HOMO-LUMO, NBO, MEP analysis and molecular docking study of 3-methyl-4-{(E)-[4-methylsulfanyl)-benzylidene]amino}1H-1,2, 4triazole-5(4H)-thione”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 151, 198-207, 2015.
29. Murugavel S, Vıjayakumar S, Nagarajan S, Ponnuswamy A. ‘Crystal structure and DFT studies of 4-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(3-methoxyphenyl)pyrimidin-2amine”. Journal of the Chilean Chemical Society, 59, 2640-2646, 2014.