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Structural, Vibrational and UV/Vis Studies of Adamantane-Containing Triazole Thiones by Spectral, DFT and Multi-reference ab initio Methods

  • Maksim Shundalau EMAIL logo , Yuliya L. Mindarava , Anna S. Matsukovich , Sergey V. Gaponenko , Ali A. El-Emam and Hamad N. Alkahtani
Published/Copyright: March 28, 2019
Zeitschrift für Physikalische Chemie
From the journal Zeitschrift für Physikalische Chemie Volume 234 Issue 1

Abstract

The Fourier transform infrared and Raman spectra of two adamantane-containing triazole thiones, namely 3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione and 3-(adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione, were examined in the ranges of 3200–650 cm−1 and 3200–150 cm−1, respectively. The density functional theory calculations were performed for the geometric structures and vibrational spectra for the title molecules. The accurate equilibrium geometry structures of the molecules were determined on the basis of full geometry optimization at the B3LYP/cc-pVDZ level of the theory. The IR and Raman vibrational spectra were calculated and compared with the experimental ones. The experimental vibrational FT-IR and Raman spectra were interpreted. Based on the structure of the molecules the biological activity indices were predicted. It is established that compounds under consideration are very likely to exhibit the analgesic activities. The UV/Vis spectra of solution of the compounds in ethanol were measured in the range of 450–200 nm. The UV/Vis spectra simulations at the Time-Dependent DFT and Multi-Reference Perturbation Theory levels of theory demonstrate unsuitability of the TDDFT for description of the experimental spectra of the title molecules. It is highly probable that this is a consequence of the intramolecular charge transfer. In contrast, the MRPT results are in a good agreement with the experimental spectra.

Keywords: 3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione; 3-(adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione; biological activity; multi-reference perturbation theory calculations; UV/Vis spectrum; vibrational spectra

Funding source: Belarusian Republican Foundation for Fundamental Research

Award Identifier / Grant number: Nr. F18MS-046

Funding statement: This work has been supported by the Belarusian Republican Foundation for Fundamental Research (Funder Id: http://dx.doi.org/10.13039/100007595, Nr. F18MS-046). Ali A. El-Emam and Hamad M. Alkahtani also extend their appreciation to the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University for funding this research.

References

1. G. Lamoureux, G. Artavia, Curr. Med. Chem. 17 (2010) 2967.10.2174/092986710792065027Search in Google Scholar PubMed

2. J. Liu, D. Obando, V. Liao, T. Lifa, R. Codd, Eur. J. Med. Chem. 46 (2011) 1949.10.1016/j.ejmech.2011.01.047Search in Google Scholar PubMed

3. G. Ali Mansoori, P. L. Barros de Araujo, E. Silvano de Araujo, Diamondoid Molecules: With Applications in Biomedicine, Materials Science, Nanotechnology & Petroleum Science, World Scientific Publishing, Hackensack (2012).10.1142/7559Search in Google Scholar

4. F. G. Hayden, Antiviral Res. 71 (2006) 372.10.1016/j.antiviral.2006.05.016Search in Google Scholar PubMed

5. I. Stylianakis, A. Kolocouris, N. Kolocouris, G. Fytas, G. B. Foscolos, E. Padalko, J. Neyts, E. de Clercq, Bioorg. Med. Chem. Lett. 13 (2003) 1699.10.1016/S0960-894X(03)00231-2Search in Google Scholar PubMed

6. N. A. Ilyushina, N. V. Bovin, R. G. Webster, E. A. Govorkova, Antiviral Res. 70 (2006) 121.10.1016/j.antiviral.2006.01.012Search in Google Scholar PubMed

7. G. Zoidis, C. Fytas, I. Papanastasiou, G. B. Foscolos, G. Fytas, E. Padalko, E. de Clercq, L. Naesens, J. Neyts, N. Kolocouris, Bioorg. Med. Chem. 14 (2006) 3341.10.1016/j.bmc.2005.12.056Search in Google Scholar PubMed

8. A. A. El-Emam, O. A. Al-Deeb, M. A. Al-Omar, J. Lehmann, Bioorg. Med. Chem. 12 (2004) 5107.10.1016/j.bmc.2004.07.033Search in Google Scholar PubMed

9. M. Protopopova, C. Hanrahan, B. Nikonenko, R. Samala, P. Chen, J. Gearhart, L. Einck, C. A. Nacy, J. Antimicrob. Chemother. 56 (2005) 968.10.1093/jac/dki319Search in Google Scholar PubMed

10. A. A. El-Emam, A.-M. S. Al-Tamimi, M. A. Al-Omar, K. A. Alrashood, E. E. Habib, Eur. J. Med. Chem. 68 (2013) 96.10.1016/j.ejmech.2013.07.024Search in Google Scholar PubMed

11. A. A. Kadi, E. S. Al-Abdullah, I. A. Shehata, E. E. Habib, T. M. Ibrahim, A. A. El-Emam, Eur. J. Med. Chem. 45 (2010) 5006.10.1016/j.ejmech.2010.08.007Search in Google Scholar PubMed

12. K. Omar, A. Geronikaki, P. Zoumpoulakis, C. Camoutsis, M. Soković, A. Ćirić, J. Glamoćlija, Bioorg. Med. Chem. 18 (2010) 426.10.1016/j.bmc.2009.10.041Search in Google Scholar PubMed

13. A. A. Kadi, N. R. El-Brollosy, O. A. Al-Deeb, E. E. Habib, T. M. Ibrahim, A. A. El-Emam, Eur. J. Med. Chem. 42 (2007) 235.10.1016/j.ejmech.2006.10.003Search in Google Scholar PubMed

14. E. S. Al-Abdullah, H. H. Asiri, S. Lahsasni, E. E. Habib, T. M. Ibrahim, A. A. El-Emam, Drug Des. Dev. Ther. 8 (2014) 505.10.2147/DDDT.S62465Search in Google Scholar PubMed PubMed Central

15. O. Kouatly, A. Geronikaki, C. Kamoutsis, D. Hadjipavlou-Litina, P. Eleftheriou, Eur. J. Med. Chem. 44 (2009) 1198.10.1016/j.ejmech.2008.05.029Search in Google Scholar PubMed

16. O. A. Al-Deeb, M. A. Al-Omar, N. R. El-Brollosy, E. E. Habib, T. M. Ibrahim, A. A. El-Emam, Arzneim.-Forsch./Drug Res. 56 (2006) 40.10.1055/s-0031-1296699Search in Google Scholar

17. S. Riganas, I. Papanastasiou, G. B. Foscolos, A. Tsotinis, J.-J. Bourguignon, G. Serin, J.-F. Mirjolet, K. Dimas, V. N. Kourafalos, A. Eleutheriades, V. I. Moutsos, H. Khan, S. Georgakopoulou, A. Zaniou, M. Prassa, M. Theodoropoulou, S. Pondiki, A. Vamvakides, Bioorg. Med. Chem. 20 (2012) 3323.10.1016/j.bmc.2012.03.038Search in Google Scholar PubMed

18. E. S. Al-Abdullah, H. H. Asiri, A. El-Emam, S. W. Ng, Acta Cryst. E 68 (2012) o344.10.1107/S160053681105570XSearch in Google Scholar PubMed PubMed Central

19. E. S. Al-Abdullah, H. H. Asiri, A. El-Emam, S. W. Ng, Acta Cryst. E 68 (2012) o345.10.1107/S1600536811055711Search in Google Scholar PubMed PubMed Central

20. M. B. Shundalau, E. S. Al-Abdullah, E. V. Shabunya-Klyachkovskaya, A. V. Hlinisty, O. A. Al-Deeb, A. A. El-Emam, S. V. Gaponenko, J. Mol. Struct. 1115 (2016) 258.10.1016/j.molstruc.2016.02.092Search in Google Scholar

21. A. M. Andrianov, I. A. Kashyn, V. M. Andrianov, M. B. Shundalau, A. V. Hlinisty, S. V. Gaponenko, E. V. Shabunya-Klyachkovskaya, A. Matsukovich, A.-M. S. Al-Tamimi, A. A. El-Emam, J. Chem. Sci. 128 (2016) 1933.10.1007/s12039-016-1188-8Search in Google Scholar

22. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A, Montgomery Jr, J. Comp. Chem. 14 (1993) 1347.10.1002/jcc.540141112Search in Google Scholar

23. Gordon Group/GAMESS homepage. Available from world wide web: http://www.msg.ameslab.gov/GAMESS/GAMESS.html [cited July, 31, 2018]Search in Google Scholar

24. B. M. Bode, M. S. Gordon, J. Mol. Graph. Model. 16 (1998) 133.10.1016/S1093-3263(99)00002-9Search in Google Scholar PubMed

25. L. J. Farrugia, J. Appl. Cryst. 30 (1997) 565.10.1107/S0021889897003117Search in Google Scholar

26. T. H. Dunning Jr, J. Chem. Phys. 90 (1989) 1007.10.1063/1.456153Search in Google Scholar

27. A. D. Becke, J. Chem. Phys. 98 (1993) 5648.10.1063/1.464913Search in Google Scholar

28. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 37 (1988) 785.10.1103/PhysRevB.37.785Search in Google Scholar

29. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 98 (1994) 11623.10.1021/j100096a001Search in Google Scholar

30. F. Jensen, Introduction to Computational Chemistry, 2nd ed., John Wiley, Chichester (2007).Search in Google Scholar

31. E. Runge, E. K. U. Gross, Phys. Rev. Lett. 52 (1984) 997.10.1103/PhysRevLett.52.997Search in Google Scholar

32. K. Burke, J. Werschnik, E. K. U. Gross, J. Chem. Phys. 123 (2005) 062206.10.1063/1.1904586Search in Google Scholar PubMed

33. T. Yanai, D. P. Tew, N. C. Handy, Chem. Phys. Lett. 393 (2004) 51.10.1016/j.cplett.2004.06.011Search in Google Scholar

34. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 113 (2009) 6378.10.1021/jp810292nSearch in Google Scholar PubMed

35. A. A. Granovsky, J. Chem. Phys. 134 (2011) 214113.10.1063/1.3596699Search in Google Scholar PubMed

36. A. A. Granovsky, Firefly version 8. Available from world wide web: http://classic.chem.msu.su/gran/firefly/index.html [cited July, 31, 2018]Search in Google Scholar

37. D. S. Druzhilovskiy, A. V. Rudik, D. A. Filimonov, T. A. Gloriozova, A. A. Lagunin, A. V. Dmitriev, P. V. Pogodin, V. I. Dubovskaya, S. M. Ivanov, O. A. Tarasova, V. M. Bezhentsev, K. A. Murtazalieva, M. I. Semin, I. S. Maiorov, A. S. Gaur, G. N. Sastry, V. V. Poroikov, Russ. Chem. Bull., Int. Ed. 66 (2017) 1832.10.1007/s11172-017-1954-xSearch in Google Scholar

38. A. Lagunin, A. Stepanchikova, D. Filimonov, V. Poroikov, Bioinformatics 16 (2000) 747.10.1093/bioinformatics/16.8.747Search in Google Scholar PubMed

39. PASS Online. Available from world wide web: http://way2drug.com/passonline/index.php [cited July, 31, 2018].Search in Google Scholar

40. H. Kubinyi, J. Braz. Chem. Soc. 13 (2002) 717.10.1590/S0103-50532002000600002Search in Google Scholar

41. I. Hargittai, K. Hedberg, In: Molecular Structures and Vibrations. S. J. Cyvin (Ed.), Elsevier, New York (1972), P. 340Search in Google Scholar

42. M. S. Almutairi, A. A. El-Emam, N. R. El-Brollosy, M. Said-Abdelbaky, S. Garcıa-Granda, Acta Cryst. E 68 (2012) o2247.10.1107/S1600536812028644Search in Google Scholar

43. N. W. Larsen, J. Mol. Struct. 51 (1979) 175.10.1016/0022-2860(79)80292-6Search in Google Scholar

44. S. Gunasekaran, B. Anita, Indian J. Pure & Appl. Phys. 46 (2008) 833.Search in Google Scholar

45. K. Kuchitsu (Ed.), Structure of Free Polyatomic Molecules. Basic Data, Springer, New York (1998).10.1007/978-3-642-45748-7Search in Google Scholar

46. L. Bistričić, G. Baranović, K. Mlinarić-Majerski, Spectrochim. Acta A 51 (1995) 1643.10.1016/0584-8539(95)01416-RSearch in Google Scholar

47. E. I. Bagrij, Adamantanes, Moscow, Nauka (1989) [in Russian].Search in Google Scholar

48. R. M. Silverstein, F. X. Webster, D. J. Kiemle, Spectrometric Identification of Organic Compounds, 7th ed., John Wiley, New York (2005)Search in Google Scholar

49. L. Goodman, A. G. Ozkabak, S. N. Thakur, J. Phys. Chem. 95 (1991) 9044.10.1021/j100176a008Search in Google Scholar

50. P. J. Hendra, D. B. Powell, Spectrochim. Acta 18 (1962) 299.10.1016/S0371-1951(62)80138-6Search in Google Scholar

51. Ö. Alver, C. Parlak, M. Şenyel, Spectrochim. Acta A 67 (2007) 793.10.1016/j.saa.2006.08.035Search in Google Scholar

52. S. A. Kudchadker, C. N. R. Rao, Indian J. Chem. 11 (1973) 140.Search in Google Scholar

53. F. Billes, H. Endrédi, G. Keresztury, J. Mol. Struct. (Theochem) 530 (2000) 183.10.1016/S0166-1280(00)00340-7Search in Google Scholar

54. V. Krishnakumar, R. J. Xavier, Spectrochim. Acta A 60 (2004) 709.10.1016/S1386-1425(03)00281-6Search in Google Scholar

55. S. Thomas, N. Biswas, S. Venkateswaran, S. Kapoor, R. D’Cunha, T. Mukherjee, Chem. Phys. Lett. 402 (2005) 361.10.1016/j.cplett.2004.12.064Search in Google Scholar

56. K. Bahgat, S. Fraihat, Spectrochim. Acta A 135 (2015) 1145.10.1016/j.saa.2014.05.081Search in Google Scholar PubMed

57. A. K. Srivastava, A. Kumar, N. Misra, P. S. Manjula, B. K. Sarojini, B. Narayana, J. Mol. Struct. 1107 (2016) 137.10.1016/j.molstruc.2015.11.042Search in Google Scholar

Supplementary Material

The online version of this article offers supplementary material (DOI: https://doi.org/10.1515/zpch-2018-1271).

Received: 2018-07-31
Accepted: 2019-02-25
Published Online: 2019-03-28
Published in Print: 2020-01-28

©2020 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

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  2. The Maximum of Minimal Conductivity in Aqueous Electrolytes
  3. The Effect of Low Weight Percent Multiwalled Carbon Nanotubes on the Dielectric Properties of Non-Conducting Polymer/Ceramic Nanocomposites for Energy Storage Materials
  4. Synthesis, Characterization and Electrical Conductivity of Silver Doped Polyvinyl Acetate/Graphene Nanocomposites: A Novel Humidity Sensor
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  8. Structural, Vibrational and UV/Vis Studies of Adamantane-Containing Triazole Thiones by Spectral, DFT and Multi-reference ab initio Methods
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https://doi.org/10.1515/zpch-2018-1271
Keywords for this article
3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione; 3-(adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione; biological activity; multi-reference perturbation theory calculations; UV/Vis spectrum; vibrational spectra

Articles in the same Issue

  1. Frontmatter
  2. The Maximum of Minimal Conductivity in Aqueous Electrolytes
  3. The Effect of Low Weight Percent Multiwalled Carbon Nanotubes on the Dielectric Properties of Non-Conducting Polymer/Ceramic Nanocomposites for Energy Storage Materials
  4. Synthesis, Characterization and Electrical Conductivity of Silver Doped Polyvinyl Acetate/Graphene Nanocomposites: A Novel Humidity Sensor
  5. Preparation, Physical Characterization and Adsorption Properties of Synthesized Co–Ni–Cr Nanocomposites for Highly Effective Removal of Nitrate: Isotherms, Kinetics and Thermodynamic Studies
  6. New Heterocyclic Derivative to Stop Carbon Steel Corrosion
  7. Investigating of Erosion-Corrosion Behavior of Carbon Steel in Egyptian Crude Oil-Water Mixture Using Electrochemical Method
  8. Structural, Vibrational and UV/Vis Studies of Adamantane-Containing Triazole Thiones by Spectral, DFT and Multi-reference ab initio Methods
  9. The Effect of Grain Size and Shape on Sliding Friction of Wet Granular Media
  10. Decomposition Kinetics of Levofloxacin: Drug-Excipient Interaction
  11. ZnO/UV/H2O2 Based Advanced Oxidation of Disperse Red Dye
  12. An Efficient Ultrasonic-Assisted Synthesis and Nonlinear Optical Property of Donor (D) -π-Acceptor (A) Chalcone (DDFP)
  13. Synthesized and Photocatalytic Mechanism of the NiO Supported YMnO3 Nanoparticles for Photocatalytic Degradation of the Methyl Orange Dye
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