Synthesis, spectral characterization, and theoretical investigation of Pd(II) complex incorporating unsymmetrical tetradentate Schiff base ligand and its application in Suzuki–Miyaura cross-coupling reaction

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 (PNU), 19395-4697, Tehran, Iran

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

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

5 Catalysis Division, Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran

Abstract

A new palladium(II) complex is synthesized via the treatment of unsymmetrical tetradentate Schiff base (H2LUns) with Pd(CH3COO)2. An analytical technique like combustion analysis for the estimation of C, H, and N and other spectroscopic techniques such as FT-IR and 1H NMR were used to elucidate the structural confirmation of the synthesized complex. Furthermore, the theoretical parameters of the optimized structures calculated by the DFT employing the B3LYP/Def2-TZVP level of theory were carried out to correlate the calculated findings with the actual data obtained experimentally. The spectroscopic and theoretical data findings revealed that the ligand is coordinated via phenolic oxygen and imine nitrogen atoms. Moreover, the catalytic activity of the palladium(II) complex was studied in the Suzuki-Miyaura cross-coupling reactions (SMCR).

Graphical Abstract

Synthesis, spectral characterization, and theoretical investigation of Pd(II) complex incorporating unsymmetrical tetradentate Schiff base ligand and its application in Suzuki–Miyaura cross-coupling reaction

Keywords


  1. Shit, M. Nandy, D. Saha, L. Zhang, W. Schmitt, C. Rizzoli, T. N. G. Row, J. Coord. Chem. 2016, 69, 2403-2414.
  2. Beigi, A. H. Kianfar, H. Farrokhpour, M. Roushani, M. H. Azarian, W. A. K. Mahmood, J. Mol. Liq. 2018, 249, 117-125.
  3. Kia, H. Kargar, J. Coord. Chem. 2015, 68, 1441-1451.
  4. Ghorbanloo, S. Jafari, R. Bikas, M. S. Krawczyk, T. Lis, Inorg. Chim. Acta 2017, 455, 15-24.
  5. D. M. Mohamad, E. R. El-Shrkawy, M. F. I. Al-Hussein, M. S. S. Adam, J. Taiwan Inst. Chem. Eng. 2020, 113, 27-45.
  6. H. Kianfar, P. Montazeri Najafabadi, M. Sedighipoor, M. M. Momeni, H. Görls, W. Plass, Gh. Mohammadnezhad, Inorg. Chem. Res. 2021, 5, 60-81.
  7. L. Pratihar, P. Mandal, C. K. Lai, S. Chattopadhyay, Polyhedron 2019, 161, 317-324.
  8. L. Li, S. S. Feng, T. Zhang, L. Wang, W. K. Dong, Inorg. Chim. Acta 2022, 534, 120815.
  9. N. Ibrahim, M. Shamsuddin, Crystal Structure Theory and Applications, 2012, 1, 25-29.
  10. Mirković, M. Radović, D. Stanković, S. Vranješ-Đurić, D. Janković, D. Petrović, L. E. Mihajlović-Lalić, Ž. Prijović, Z. Milanović, J. Coord. Chem. 2022, 75, 211-224.
  11. H. Abdel-Rahman, M. S. Adam, N. Al-Zaqri, M. R. Shehata, H. E. Ahmed, S. K. Mohamed, Arab. J. Chem. 2022, 15, 103737.
  12. Shaghaghi, N. Kalantari, M. Kheyrollahpoor, M. Haeili, J. Mol. Struct. 2020, 1200, 127107.
  13. Sabate, R. Gavara, I. Giannicchi, R. Bosque, A. D. Cort, L. Rodriguez, New J. Chem. 2016, 40, 5714-5721.
  14. S. More, S. B. Pawal, S. R. Lolage, S. S. Chavan, J. Mol. Struct. 2017, 1128, 419-427.
  15. Debono, M. Iglesias, F. Sanchez, Adv. Synth. Catal. 2007, 349, 2470-2476.
  16. J. Jin, D. H. Lee, Angew. Chem. Int. Ed. 2010, 49, 1119-1122.
  17. H. Yang, Y. H. Liu, S. M. Peng, S. T. Liu, Mol. Catal. 2022, 522, 112232.
  18. Balali, M. Bagherzadeh, R. Nejat, H. Keypour, Inorg. Chem. Res. 2021, 5, 82-93.
  19. R. Borhade, S. B. Waghmode, Tetrahedron Lett. 2008, 49, 3423-3429.
  20. M. Tajuddin, H. Bahron, S. N. Ahmad, Sci. Res. J. 2015, 12, 2-16.
  21. N. Ahmad, H. Bahron, A. M. Tajuddin, Int. J. Eng. Technol. 2018, 7, 15-19.
  22. M. Ansari, B. R. Bhat, J. Chem. Sci. 2017, 129, 1483-1490.
  23. E. Balsane, S. S. Shendage, J. M. Nagarkar, J. Chem. Sci. 2015, 127, 425-431.
  24. Sedighipoor, A. H. Kianfar, G. Mohammadnezhad, H. Görls, W. Plass, Inorg. Chim. Acta 2018, 476, 20-26.
  25. Minakata, M. Komatsu, Chem. Rev. 2009, 109, 711-724.
  26. Kargar, M. Moghadam, L. Shariati, N. Feizi, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, J. Mol. Struct. 2022, 1257, 132608.
  27. Kargar, A. Moghimi, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K. S. Munawar, J. Sulfur Chem. 2022, 43, 22-36.
  28. Kargar, M. Bazrafshan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K. S. Munawar, M. Ashfaq, M. N. Tahir, Polyhedron 2021, 202, 115194.
  29. 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.
  30. Kargar, A. Kaka-Naeini, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. Amiri Rudbari, K. S. Munawar, J. Coord. Chem. 2021, 74, 1563-1583.
  31. 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.
  32. 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.
  33. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, M. N. Tahir, J. Mol. Struct. 2019, 1179, 732-738.
  34. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, M. N. Tahir, J. Iran. Chem. Soc. 2019, 16, 1081-1090.
  35. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, A. Sahraei, M.N. Tahir, Struct. Chem. 2019, 30, 2289-2299.
  36. Kargar, M. Fallah-Mehrjardi, Inorg. Chem. Res. 2021, 5, 201-206.
  37. Fallah-Mehrjardi, H. Kargar, Inorg. Chem. Commun. 2021, 134, 109016.
  38. M. 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.
  39. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
  40. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3094.
  41. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
  42. Gauss, J. Chem. Phys. 1993, 99, 3629-3643.
  43. http://www.chemissian.com.
  44. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, C. R. Landis, F. Weinhold, University of Wisconsin, Madison, 2018.
  45. 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, 61-71.
  46. A. Blackburn, B. J. Coe, J. Fielden, M. Helliwell, J. J. W. McDouall, M. G. Hutchings, Inorg. Chem. 2010, 49, 9136-9150.
  47. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, A. Sahraei, M. N. Tahir, J. Mol. Struct. 2020, 1205, 127642.
  48. Ilhan, H. Temel, I. Yilmaz, M. Sekerci, Polyhedron 2007, 26, 2795-2802.
  49. A. Palafox, Phys. Sci. Rev. 2018, 3, 1-30.
  50. Tabares-Mendoza, P. Guadarrama, J. Organomet. Chem. 2006, 691, 2978-2986.
  51. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev. 2003, 103, 1793-1874.
  52. Demircioğlu, Ç. Albayrak, O. Büyükgüngör, J. Mol. Struct. 2014, 1065-1066, 210-222.
  53. Wei, Y. She, Y. Yu, X. Yao, S. Zhang, J. Mol. Model. 2012, 18, 2483-2491.
Volume 6, Issue 1
Spring and Summer; Special Issue: In Memory of Prof. Mehdi Rashidi
2022
Pages 76-83
  • Receive Date: 15 April 2022
  • Revise Date: 30 May 2022
  • Accept Date: 31 May 2022