Inorganic Chemistry Research

New copper(II) complexes with benzimidazole and benzoxazole heterocyclic ligands: synthesis, spectral characterization, FMO, MEP, NBO, and DFT study

Document Type : Research Paper

Authors

1 Department of Chemical Engineering, Faculty of Engineering, Ardakan University, P.O. Box 184, Ardakan, Iran.

2 Department of Chemistry, Payame Noor University, 19395-3697, Tehran, Iran

3 Department of Chemistry, University of Sargodha, Punjab, Pakistan

4 Department of Chemistry, University of Mianwali, Mianwali, Pakistan

10.22036/icr.2022.327584.1124

Abstract

3-Ethoxy salicylaldehyde on reaction with 1,2-phenylenediamine and 2-aminophenol yielded heterocyclic ligands (HLBIZ and HLBOZ) under ultrasonic irradiation in ethanol solvent. The reaction of these ligands with copper(II) acetate monohydrate salt led to the related Cu(L)2 complexes in methanol solvent. FT-IR, 1H & 13C NMR, and elemental analysis were used to investigate the structures of the synthesized ligands, while the copper(II) complexes were characterized by CHN analysis and FT-IR spectroscopy. The imino nitrogens and phenolic oxygens are involved in the coordination of the ligands to the Cu2+ ions to generate the complex. The parameters estimated by DFT at the B3LYP/Def2-TZVP level of theory show that the theoretical values are consistent with the experimental findings.

Graphical Abstract

New copper(II) complexes with benzimidazole and benzoxazole heterocyclic ligands: synthesis, spectral characterization, FMO, MEP, NBO, and DFT study

Keywords

  1. Mathur, S. Bargotya, J. Appl. Chem. 2017, 10, 18.
  2. Mathur, N. Jain, A. K. Sharma, Open Pharm. Sci. J. 2018, 5, 24.
  3. G. Cassemiro, J. S. Santos, W. X. Oliveira, E. C. Pereira-Maia, B. R. Galvao, W. D. do Pim, P. P. Silva-Caldeira, Appl. Organomet. Chem. 2020, 34, e5425.
  4. Klimesova, J. Koci, K. Waisser, J. Kaustova, Il Farmaco, 2002, 57, 259.
  5. M. Agh-Atabay, B. Dulger, F. Gucin, Eur. J. Med. Chem. 2003, 38, 875.
  6. Tavman, N. M. Agh-Atabay, A. Neshat, F. Gucin, B. Dulger, D. Haciu, Transition Met. Chem. 2006, 31, 194.
  7. Khalafi-Nezhad, M. N. Soltani Rad, H. Mohabatkar, Z. Asrari, B. Hemmateenejad, Bioorg. Med. Chem. 2005, 13, 1931.
  8. Mann, A. Baron, Y. Opoku-Boahen, E. Johansson, G. Parkinson, L. R. Kelland, S. Neidle, J. Med. Chem. 2001, 44, 138.
  9. L. Adams, J. C. Boehm, T. F. Gallagher, S. Kassis, E. F. Webb, R. Hall, M. Sorenson, R. Garigipati, D. E. Griswold, J. C. Lee, Bioorg. Med. Chem. Lett. 2001, 11, 2867.
  10. K. Ujjinamatada, A. Baier, P. Borowski, R.S. Hosmane, Bioorg. Med. Chem. Lett. 2007, 17, 2285.
  11. A.F. Rostom, H.M.A. Ashour, H.A.A.E. Razik, A.E.F.H.A.E. Fattah, N.N. El-Din, Bioorg. Med. Chem. 2009, 17, 2410.
  12. B. Ulkuseven, A. Tavman, G. Otuk, S. Birteksoz, Folia Microbiol. 2002, 47, 481.
  13. M. Agh-Atababy, A. Baykal, M. Somer, Transition Met. Chem. 2004, 29, 159.
  14. Tavman, B. Ulkuseven, Main Group Met. Chem. 2001, 24, 205.
  15. Kumari, S. Adhikari, J.S. Matalobos, D. Das, J. Mol. Struct. 2018, 1151, 169.
  16. Zhao, S. Zhi, H. Yu, R. Mao, J. Hu, W. Song, J. Zhang, RSC Adv. 2017, 7, 51162.
  17. Dyukova, L.G. Lavrenova, T.A. Kuzmenko, V.Y. Komarov, T.S. Sukhikh, E.V. Vorontsova, Chim. Acta 2019, 486, 406.
  18. Shankar, F. Hussain, M. Sathiyendiran, J. Organomet. Chem. 2012, 719, 26.
  19. Lukevics, P. Arsenyan, I. Shestakova, I. Domracheva, A. Nesterova, O. Pudova, Eur. J. Med. Chem. 2001, 36, 507.
  20. Wu, F. Kou, F. Jia, B. Liu, J. Yuan, Y. Bai, Bioinorg. Chem. Appl. 2011, 105431.
  21. Hu, C. Liao, R. Mao, J. Zhang, J. Zhao, Z. Gu, Med. Chem. Comm. 2018, 9, 337.
  22. Naveen, R. Jain, P. Kalaivani, R. Shankar, F. Dallemer, R. Prabhakaran, New J. Chem. 2017, 41, 8885.
  23. Y. Qi, Q. Gan, Y.X. Liu, Y.H. Xiong, Z.W. Mao, X.Y. Le, Eur. J. Med. Chem. 2018, 154, 220.
  24. Wang, N. Ling, Q.T. Che, Y.W. Zhang, H.X. Yang, Y. Ruan, T.T. Zhao, Inorg. Chem. Commun. 2019, 105, 97.
  25. F. Back, G.M. de Oliveira, M.A. Ballin, V.A. Corbellini, Inorg. Chim. Acta 2010, 363, 807.
  26. Razavi, S.K. Palaninathan, E.T. Powers, R.L. Wiseman, H.E. Purkey, N.N. Mohamedmohaideen, S. Deechongkit, K.P. Chiang, M.T.A. Dendle, J.C. Sacchettini, J.W. Kelly, Angew. Chem., Int. Ed. 2003, 115, 2864.
  27. Razavi, S.K. Palaninathan, E.T. Powers, R.L. Wiseman, H.E. Purkey, N.N. Mohamedmohaideen, S. Deechongkit, K.P. Chiang, M.T.A. Dendle, J.C. Sacchettini, J.W. Kelly, Angew. Chem., Int. Ed. 2003, 115, 2758.
  28. Koci, V. Klimesova, K. Waisser, J. Kaustova, H.M. Dahse, U. Mollmann, Bioorg. Med. Chem. Lett. 2002, 12, 3275.
  29. F. Shi, T.D. Bradshaw, S. Wrigley, C.J. McCall, P. Lelieveld, I. Fichtner, M.F. Stevens, J. Med. Chem. 1996, 39, 3375.
  30. Wu, X. Han, Y. Qu, K. Zhao, C. Wang, G. Huang, H. Wu, J. Mol. Struct. 2019, 1191, 95.
  31. Marcinkowski, M. A. Fik, T. Luczak, M. Kubicki, V. Patroniak, Polyhedron 2018, 141, 125.
  32. Chacko, H. Boshoff, V. Singh, D. M. Ferraris, D. R. Gollapalli, M. J. Zhang, A. P. Lawson, M. J. Pepi, A. Joachimiak, M. Rizzi, V. Mizrahi, G. D. Cuny, L. Hedstrom, J. Med. Chem. 2018, 61, 4739.
  33. Jiang, X. Tang, W. Dou, H. Zhang, W. Liu, C. Wang, J. Zheng, J. Inorg. Biochem. 2010, 104, 583.
  34. I. Knyazhanskii, P. V. Gilyanovskii, A. E. Lyubarskaya, Zh. Obshch. Khim. 1980, 50, 2553.
  35. Spengler, A. Kincses, B. Racz, B. Varga, G. Watanabe, R. Saijo, H. Sekiya, E. Tamai, J. Maki, J. Molnar, M. Kawase, Anticancer Res. 2018, 38, 6181.
  36. Sahraei, H. Kargar, M. Hakimi, M. N. Tahir, J. Mol. Struct. 2017, 1149, 576.
  37. Sahraei, H. Kargar, M. Hakimi, M. N. Tahir, Transition Met. Chem. 2017, 42, 483.
  38. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, M. N. Tahir, J. Mol. Struct. 2019, 1179, 732.
  39. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, A. Sahraei, M. N. Tahir, Struct. Chem. 2019, 30, 2289.
  40. Kargar, A. Adabi Ardakani, K. S. Munawar, M. Ashfaq, M. N. Tahir, J. Iran. Chem. Soc. 2021, 18, 2493.
  41. Kargar, R. Behjatmanesh-Ardakani, V. Torabi, M. Kashani, Z. Chavoshpour-Natanzi, Z. Kazemi, V. Mirkhani, A. Sahraei, M. N. Tahir, M. Ashfaq, K. S. Munawar, Polyhedron 2021, 195, 114988.
  42. Kargar, R. Behjatmanesh-Ardakani, V. Torabi, A. Sarvian, Z. Kazemi, Z. Chavoshpour-Natanzi, V. Mirkhani, A. Sahraei, M. N. Tahir, M. Ashfaq, K. S. Munawar, Inorg. Chim. Acta 2021, 514, 120004.
  43. Kargar, M. Bazrafshan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K. S. Munawar, M. Ashfaq, M. N. Tahir, Polyhedron 2021, 202, 115194.
  44. Kargar, P. Forootan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K.S. Munawar, M. Ashfaq, M. N. Tahir, Inorg. Chim. Acta 2021, 523, 120414.
  45. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, M. Ashfaq, M. N. Tahir, J. Mol. Struct. 2021, 1241, 130653.
  46. S. Yeap, H. Karagr, R. Kia, A. Jamshidvand, H.-K. Fun, Acta Cryst. 2009, E65, o745.
  47. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, etc. GAUSSIAN 09 (Revision D.01), Gaussian, Inc., C.T. Wallingford (2013).
  48. D. Becke, J. Chem. Phys. 1993, 98, 5648.
  49. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999.
  50. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297.
  51. Gauss, J. Chem. Phys. 1993, 99, 3629.
  52. http://www.chemissian.com.
  53. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, C. R. Landis, F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison, WI (2013).
  54. Jamshidvand, M. Sahihi, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, H. Amiri Rudbari, H. Kargar, R. Keshavarzi, S. Gharaghani, J. Mol. Liq. 2018, 253, 61.
  55. Khera, A. K. Sharma, N. K. Kaushik, Polyhedron 1983, 2, 1177.
  56. Gupta, R. Sharan, R. N. Kapoor, Transition Met. Chem. 1978, 3, 282.
  57. D. Crane, R. Hughes, E. Sinn, Inorg. Chim. Acta 1995, 237, 181.
  58. A. Palafox, Phys. Sci. Rev. 2018, 3, 1.
  59. Quezada-Buendia, A. Esparza-Ruiz, A. Pena-Hueso, N. Barba-Behrens, R. Contreras, A. Flores-Parra, S. Bernes, S. E. Castillo-Blum, Inorg. Chim. Acta 2008, 361, 2759.
  60. D. Crane, R. Hughes, E. Sinn, Inorg Chim. Acta 1995, 237, 181.
  61. Benisvy, E. Bill, A. J. Blake, D. Collison, E. S. Davies, C. D. Garner, G. McArdle, E. J. L. McInnes, J. McMaster, S. H. K. Ross, C. Wilson, Dalton Trans. 2006, 258.
  62. Z. C. Fellah, J. -P. Costes, C. Duhayon, J. C. Daran, J. -P. Tuchagues, Polyhedron 2010, 29, 2111.
  63. Tabares-Mendoza, P. Guadarrama, J. Organomet. Chem. 2006, 691, 2978.
  64. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev. 2003, 103, 1793.
  65. K. Choudhary, A. K. Bhatt, D. Dash, N. Sharma, J. Comput. Chem. 2019, 40, 2354.
  66. T. Adejumo, N. V. Tzouras, L. P. Zorba, D. Radanović, A. Pevec, S. Grubišić, D. Mitić, K. K. Anđelković, G. C. Vougioukalakis, B. Čobeljić, I. Turel, Molecules 2020, 25, 4043.
  67. V. Tzouras, S. P. Neofotistos, G. C. Vougioukalakis, ACS Omega 2019, 4, 10279.
  68. Demircioğlu, Ç. Albayrak, O. Büyükgüngör, J. Mol. Struct. 2014, 1065, 210.
  69. Wei, Y. She, Y. Yu, X. Yao, S. Zhang, J. Mol. Model. 2012, 18, 2483.
Inorganic Chemistry Research
Volume 6, Issue 1
Spring and Summer; Special Issue: In Memory of Prof. Mehdi Rashidi
2022
Pages 48-57
  • Receive Date: 01 February 2022
  • Revise Date: 16 March 2022
  • Accept Date: 17 March 2022
  • First Publish Date: 10 April 2022