Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter December 2, 2021

Synthesis, characterization, and computational study of copper bipyridine complex [Cu (C18H24N2) (NO3)2] to explore its functional properties

  • Saleh S. Alarfaji , Sajjad Hussain EMAIL logo , Abdullah G. Al-Sehemi , Shabbir Muhammad ORCID logo EMAIL logo , Islam Ullah Khan , Faiz Rabbani , Mazhar Amjad Gilani and Hamid Ullah


In the present study, copper (II) complex of 4, 4′-di-tert-butyl-2,2′-bipyridine [Cu (C18H24N2) (NO3)2], 1 is investigated through its synthesis and characterization using elemental analysis technique, infra-red spectroscopy, and single-crystal analysis. The compound 1 crystallizes in orthorhombic space group P212121. The copper atom in the mononuclear complex is hexa coordinated through two nitrogen and four oxygen atoms from bipyridine ligand and nitrate ligands. The thermal analysis depicts the stability of the entitled compound up to 170 °C, and the decomposition takes place in different steps between 170 and 1000 °C. Furthermore, quantum chemical techniques are used to study optoelectronic, nonlinear optical, and therapeutic bioactivity. The values of isotropic and anisotropic linear polarizabilities of compound 1 are calculated as 41.65 × 10−24 and 23.02 × 10−24 esu, respectively. Likewise, the static hyperpolarizability is calculated as 47.92 × 10−36 esu using M06 functional compared with para-nitroaniline (p-NA) and found several times larger than p-NA. Furthermore, the antiviral potential of compound 1 is studied using molecular docking technique where intermolecular interactions are checked between the entitled compound and two crucial proteins of SARS-CoV-2 (COVID-19). Our investigation indicated that compound 1 interacts more vigorously to spike protein than main protease (MPro) due to its better binding energy of −9.60 kcal/mol compared with −9.10 kcal/mol of MPro. Our current study anticipated that the above-entitled coordination complexes could be potential candidates for optoelectronic properties and their biological activity.

Corresponding authors: Sajjad Hussain, School of Chemistry, Faculty of Basic Sciences and Mathematics, Minhaj University, Lahore, Pakistan, E-mail: ; and Shabbir Muhammad, Department of Physics, College of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia, E-mail:

Funding source: King Khalid University

Award Identifier / Grant number: RGP.1/168/42

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The author from King Khalid University Saudi Arabia extends his appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through Research Projects (RGP.1/168/42).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.


1. Bredas, JL, Adant, C, Tackx, P, Persoons, A, Pierce, B. Third-order nonlinear optical response in organic materials: theoretical and experimental aspects. Chem Rev 1994;94:243–78. in Google Scholar

2. Muhammad, S, Nakano, M. Quantum chemical prospective of open-shell carbon nanomaterials for nonlinear optical applications. In: Chemical functionalization of carbon nanomaterials: chemistry and applications. United States: CRC Press; 2015:807–21 pp.Search in Google Scholar

3. Bloembergen, N. Nonlinear optics: past, present, and future. In: IEEE Journal of Selected Topics in Quantum Electronics. New York City, USA: IEEE Journal; 1992, 6:876–880 pp. in Google Scholar

4. Mohammed, AA. Accurate calculations of nonlinear optical properties using finite field methods (Doctoral dissertation). Canada: McMaster University Libraries; 2017. in Google Scholar

5. Schneider, T. Nonlinear optics in telecommunications. Berlin, Germany: Springer Science & Business Media; 2013.Search in Google Scholar

6. Yue, S, Slipchenko, MN, Cheng, JX. Multimodal nonlinear optical microscopy. Laser Photon Rev 2011;5:496–512. in Google Scholar

7. Muhammad, S, Xu, HL, Zhong, RL, Su, ZM, Al-Sehemi, AG, Irfan, A. Quantum chemical design of nonlinear optical materials by sp2-hybridized carbon nanomaterials: issues and opportunities. J Mater Chem C 2013;1:5439–49. in Google Scholar

8. Muhammad, S, Xu, H, Liao, Y, Kan, Y, Su, Z. Quantum mechanical design and structure of the Li@B10H 14 basket with a remarkably enhanced electro-optical response. J Am Chem Soc 2009;131:11833–40. in Google Scholar

9. Muhammad, S. Second-order nonlinear optical properties of dithienophenazine and TTF derivatives: a butterfly effect of dimalononitrile substitutions. J Mol Graph Model 2015;59:14–20. in Google Scholar

10. Morrall, JP, Dalton, GT, Humphrey, MG, Samoc, M. Organotransition metal complexes for nonlinear optics. Adv Organomet Chem 2007;55:61–136. in Google Scholar

11. de Lucas, AI, Martín, N, Sánchez, L, Seoane, C, Andreu, R, Garín, J, et al.. The first tetrathiafulvalene derivatives exhibiting second-order NLO properties. Tetrahedron 1998;54:4655–62. in Google Scholar

12. Saleh, BE, Teich, MC. Fundamentals of photonics. United States: John Wiley & Sons; 2019.Search in Google Scholar

13. Ballman, A, Byer, RL, Eimerl, D, Feigelson, R, Feldman, BJ, Goldberg, LS, et al.. V. Inorganic nonlinear materials for frequency conversion. Appl Opt 1987;26:224–7. in Google Scholar

14. Wolff, JJ, Wortmann, R. Organic materials for second-order non-linear optics. Advances in physical organic chemistry, Advances in physical organic chemistry 32 (1999): 121-217. Netherlands: Elsevier; 1999:121–217 pp.10.1016/S0065-3160(08)60007-6Search in Google Scholar

15. Rao, EN, Appalakondaiah, S, Yedukondalu, N, Vaitheeswaran, G. Structural, electronic and optical properties of novel carbonate fluorides ABCO3F (A = K, Rb, Cs; B = Ca, Sr). J Solid State Chem 2014;212:171–9. in Google Scholar

16. Long, NJ. Organometallic compounds for nonlinear optics—the search for en‐light‐enment! Angew Chem Int Ed Engl 1995;34:21–38. in Google Scholar

17. Whittall, I, McDonagh, AM, Humphrey, M, Samoc, M. Organometallic complexes in nonlinear optics II: third-order nonlinearities and optical limiting studies. Adv Organomet Chem 1999;43:349–405.10.1016/S0065-3055(08)60673-5Search in Google Scholar

18. Xiao, X, Rao, Z-Y, Zhang, Y-Q, Xue, S-F, Tao, Z. (4,4′-di-tert-butyl-2,2′-bipyridine-[kappa]2N,N′)bis(nitrato-[kappa]2O,O′)copper(II). Acta Crystallogr E 2009;65:m202. in Google Scholar

19. Galan, M, Sanchez-Rodriguez, J, Cangiotti, M, Garcia-Gallego, S, Jimenez, J, Gomez, R, et al.. Antiviral properties against HIV of water soluble copper carbosilane dendrimers and their EPR characterization. Curr Med Chem 2012;19:4984–94. in Google Scholar

20. Galal, SA, Abd El-All, AS, Hegab, KH, Magd-El-Din, AA, Youssef, NS, El-Diwani, HI. Novel antiviral benzofuran-transition metal complexes. Eur J Med Chem 2010;45:3035–46. in Google Scholar

21. Andreou, A, Trantza, S, Filippou, D, Sipsas, N, Tsiodras, S. COVID-19: the potential role of copper and N-acetylcysteine (NAC) in a combination of candidate antiviral treatments against SARS-CoV-2. In Vivo 2020;34(3 Suppl):1567–88. in Google Scholar

22. Sheldrick, G. SADABS v. 2.01, Bruker/Siemens area detector absorption correction program. Madison, Wisconsin, USA: Bruker AXS; 1998.Search in Google Scholar

23. Sheldrick, G. A short history of SHELX. Acta Crystallogr A: Found Crystallogr 2008;64:112. in Google Scholar

24. Sheldrick, GM. Crystal structure refinement with SHELXL. Acta Crystallogr C: Struct Chem 2015;71:3–8. in Google Scholar

25. Frisch, M, Trucks, G, Schlegel, H, Scuseria, G, Robb, M, Cheeseman, J, et al.. Gaussian 16. (Software) 2016;3. in Google Scholar

26. Zhao, Y, Truhlar, DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor Chem Acc 2008;120:215–41. in Google Scholar

27. Zhao, Y, Truhlar, DG. Applications and validations of the Minnesota density functionals. Chem Phys Lett 2011;502:1–13. in Google Scholar

28. Mohan, B, Choudhary, M, Bharti, S, Jana, A, Das, N, Muhammad, S, et al.. Syntheses, characterizations, crystal structures and efficient NLO applications of new organic compounds bearing 2-methoxy-4-nitrobenzeneamine moiety and copper (II) complex of (E)-N′-(3, 5-dichloro-2-hydroxybenzylidene) benzohydrazide. J Mol Struct 2019;1190:54–67. in Google Scholar

29. Mohan, B, Choudhary, M, Muhammad, S, Das, N, Singh, K, Jana, A, et al.. Synthesis, characterizations, crystal structures, and theoretical studies of copper(II) and nickel(II) coordination complexes. J Coord Chem 2020;73:1256–79. in Google Scholar

30. Mohan, B, Jana, A, Das, N, Bharti, S, Choudhary, M, Muhammad, S, et al.. A dual approach to study the key features of nickel (II) and copper (II) coordination complexes: synthesis, crystal structure, optical and nonlinear properties. Inorg Chim Acta 2019;484:148–59. in Google Scholar

31. Talib, SH, Baskaran, S, Yu, X, Yu, Q, Bashir, B, Muhammad, S, et al.. Non-noble metal single-atom catalyst of Co1/MXene (Mo2CS2) for CO oxidation. Sci China Mater 2021;64:651–63. in Google Scholar

32. Noorussabah, N, Choudhary, M, Das, N, Mohan, B, Singh, K, Singh, RK, et al.. Copper(II) and nickel(II) complexes of tridentate hydrazide and schiff base ligands containing phenyl and naphthalyl groups: synthesis, structural, molecular docking and density functional study. J Inorg Organomet Polym Mater 2020;30:4426–40. in Google Scholar

33. Muhammad, S, Xu, H, Su, Z, Fukuda, K, Kishi, R, Shigeta, Y, et al.. A new type of organic-inorganic hybrid NLO-phore with large off-diagonal first hyperpolarizability tensors: a two-dimensional approach. Dalton Trans 2013;42:15053–62. in Google Scholar

34. Muhammad, S, Minami, T, Fukui, H, Yoneda, K, Kishi, R, Shigeta, Y, et al.. Halide ion complexes of decaborane (B10H14) and their derivatives: noncovalent charge transfer effect on second-order nonlinear optical properties. J Phys Chem A 2012;116:1417–24. in Google Scholar

35. Dallakyan, S, Olson, AJ. Small-molecule library screening by docking with PyRx. in Chemical biology. New York, NY.: Humana Press; 2015:243–50 pp. in Google Scholar PubMed

36. Di Muzio, E, Toti, D, Polticelli, F. DockingApp: a user friendly interface for facilitated docking simulations with AutoDock Vina. J Comput Aided Mol Des 2017;31:213–8. in Google Scholar

37. Studio D. Discovery Studio Visualizer. Accelrys [21]. University of Adelaide Level 7 Ingkarni Wardli Building 5005 Adelaide, Australia: Dassault Systemes BIOVIA; 2008.Search in Google Scholar

38. Khaerunnisa, S, Kurniawan, H, Awaluddin, R, Suhartati, S, Soetjipto, S. Potential inhibitor of COVID-19 main protease (MPro) from several medicinal plant compounds by molecular docking study. Preprints; 2020:2020030226 p. Submitted for publication.10.20944/preprints202003.0226.v1Search in Google Scholar

39. Chen, J, Gao, K, Wang, R, Wei, G. Prediction and mitigation of mutation threats to COVID-19 vaccines and antibody therapies. Chem Sci 2021;12:6929–48. in Google Scholar

40. Berman, HM, Westbrook, J, Feng, Z, Gilliland, G, Bhat, TN, Weissig, H, et al.. The protein data bank. Nucleic Acids Res 2000;28:235–42. in Google Scholar

41. Xiao, X, Rao, Z-Y, Zhang, Y-Q, Xue, S-F, Tao, Z. (4, 4′-di-tert-butyl-2, 2′-bipyridine-κ2N, N′) bis (nitrato-κ2O, O′) copper (II). Acta Crystallogr E 2009;65:m202-m. in Google Scholar

42. Senthilkumar, K, Haukka, M, Nallasamy, P. Homo and dinuclear heteroleptic Zn, Cd & Pb complexes derived from FcCOOH and DTBbpy ligands: structural, luminescence and electrochemical studies. J Inorg Organomet Polym Mater 2016;26:864–75. in Google Scholar

43. Kodama, S, Nomoto, A, Yano, S, Ueshima, M, Ogawa, A. Novel heterotetranuclear V2Mo2 or V2W2 complexes with 4, 4′-di-tert-butyl-2, 2′-bipyridine: syntheses, crystal structures, and catalytic activities. Inorg Chem 2011;50:9942–7. in Google Scholar

Supplementary Material

The online version of this article offers supplementary material (

Received: 2021-09-23
Accepted: 2021-11-14
Published Online: 2021-12-02
Published in Print: 2022-05-25

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 10.12.2023 from
Scroll to top button