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Molybdenum(VI) complexes with tridentate Schiff base ligands derived from isoniazid as catalysts for the oxidation of sulfides: synthesis, X-ray crystal structure determination and spectral characterization

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Abstract

Two new complexes, including [MoO2(L1)(CH3OH)] and [MoO2(L2)(CH3OH)], with tridentate ONO–donor Schiff base ligands (H2L1: (E)-N'-(2-hydroxy-3-methoxybenzylidene)isonicotinohydrazide and H2L2: (E)-N'-(5-chloro-2-hydroxybenzylidene)isonicotinohydrazide) have been synthesized and characterized spectroscopically through FT-IR and 1H-NMR and by elemental analyses. Their solid-state structures were also confirmed by single-crystal X-ray diffraction (SC-XRD) technique. These tridentate Schiff base ligands coordinated to the metal ion via phenolate oxygen, imine nitrogen and enolic oxygen atoms. In the complexes, the molybdenum center adapts a slightly distorted octahedral geometry, by using three O,N,O-donor atoms of the tridentate ligands, methanol and an oxo group employing the axial positions, while another oxo group makes the equatorial plane. Moreover, the complexes were utilized in oxidizing the different sulfides as an efficient homogeneous catalyst in the presence of tert-butyl hydroperoxide (TBHP) as an oxidizing agent in 1,2-dichloroethane (DCE) as a solvent under refluxed conditions. This method has numerous ascendancies such as high yield, short reaction time and excellent selectivity to produce corresponding sulfoxides without overoxidation to sulfones.

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References

  1. S. Vidyacharan, C. Adhikari, V.S. Krishna, R.S. Reshma, D. Sriram, D.S. Sharada, Bioorg. Med. Chem. Lett. 27, 1593 (2017)

    Article  CAS  Google Scholar 

  2. Z.Q. Li, X.G. Bai, Q. Deng, G.N. Zhang, L. Zhou, Y.S. Liu, J.X. Wang, Y.C. Wang, Bioorg. Med. Chem. 25, 213 (2017)

    Article  CAS  Google Scholar 

  3. E. Pahlavani, H. Kargar, N. Sepehri Rad, Zahedan J. Res. Med. Sci. 17, 1 (2015)

  4. F. Martins, S. Santos, C. Ventura, R. Elvas-Leitao, L. Santos, S. Vitorino, M. Reis, V. Miranda, H.F. Correia, J. Aires-de-Sousa, V. Kovalishyn, D.A.R.S. Latino, J. Ramos, M. Viveiros, Eur. J. Med. Chem. 81, 119 (2014)

    Article  CAS  Google Scholar 

  5. L. **a, Y.F. **a, L.R. Huang, X. **ao, H.Y. Lou, T.J. Liu, W.D. Pan, H. Luo, Eur. J. Med. Chem. 97, 83 (2015)

    Article  CAS  Google Scholar 

  6. V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, E.D. Clercq, C. Pannecouque, J. Balzarini, Med. Chem. Res. 21, 1451 (2012)

    Article  CAS  Google Scholar 

  7. M. Malhotra, S. Sharma, A. Deep, Med. Chem. Res. 21, 1237 (2012)

    Article  CAS  Google Scholar 

  8. G. Nigade, P. Chavan, M. Deodhar, Med. Chem. Res. 21, 27 (2012)

    Article  CAS  Google Scholar 

  9. M. Malhotra, V. Monga, S. Sharma, J. Jain, A. Samad, J. Stables, A. Deep, Med. Chem. Res. 21, 2145 (2012)

    Article  CAS  Google Scholar 

  10. Y.Q. Hu, S. Zhang, F. Zhao, C. Gao, L.S. Feng, Z.S. Lv, Z. Xu, X. Wu, Eur. J. Med. Chem. 133, 255 (2017)

    Article  CAS  Google Scholar 

  11. M. Poggi, R. Barroso, A.J. Costa-Filho, H.B. de Barros, F. Pavan, C.Q. Leite, D. Gambino, M.H. Torre, J. Mex. Chem. Soc. 57, 198 (2013)

  12. A. Kajal, S. Bala, S. Kamboj, N. Sharma, V. Saini, J. Catalysts 2013, 1 (2013)

    Article  Google Scholar 

  13. M.J. Hearn, M.H. Cynamon, M.F. Chen, R. Coppins, J. Davis, H.J.O. Kang, A. Noble, B. Tu-Sekine, M.S. Terrot, D. Trombino, T. Minh, E.S. Webster, R. Wilson, Eur. J. Med. Chem. 44, 4169 (2009)

    Article  CAS  Google Scholar 

  14. B.A. Al-Hiyari, A.K. Shakya, R.R. Naik, S. Bardaweel, Molbank 2021, M1189 (2021)

    Article  Google Scholar 

  15. C.U. Dueke-Eze, T.M. Fasina, A.E. Oluwalana, O.B. Familoni, J.M. Mphalele, C. Onubuogu, Sci. Afr. 9, e00522 (2020)

  16. Y. Li, F. Zaera, Catal. Sci. Technol. 5, 3773 (2015)

    CAS  Google Scholar 

  17. A. Riisio, A. Lehtonen, M.M. Hanninen, R. Sillanpaa, Eur. J. Inorg. Chem. 2013, 1499 (2013)

    Article  Google Scholar 

  18. R. Bikas, V. Lippolis, N. Noshiranzadeh, H. Farzaneh-Bonab, A.J. Blake, M. Siczek, H. Hosseini-Monfared, T. Lis, Eur. J. Inorg. Chem. 2017, 999 (2017)

    Article  CAS  Google Scholar 

  19. M.M. Javadi, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, H. Kargar, M.N. Tahir, Polyhedron 72, 19 (2014)

    Article  Google Scholar 

  20. C.R. Craig, R.E. Stitzel, Modern Pharmacology with Clinical Applications, 6th edn. (Lippincott Williams & Wilkins, Baltimore, 2004)

  21. S.A. Blum, R.G. Bergman, J.A. Ellman, J. Org. Chem. 68, 150 (2003)

    Article  CAS  Google Scholar 

  22. J. Fink, High Performance Polymers, 2nd edn. (William Andrew Inc., Norwich, 2008)

  23. I. Fernandez, N. Khiar, Chem. Rev. 103, 3651 (2003)

    Article  CAS  Google Scholar 

  24. M. Bagherzadeh, L. Tahsini, R. Latifi, A. Ellern, L.K. Woo, Inorg. Chim. Acta 361, 2019 (2008)

    Article  CAS  Google Scholar 

  25. N.Y. **, J. Coord. Chem. 65, 4013 (2012)

    Article  CAS  Google Scholar 

  26. L. Wang, Y.J. Han, Q.B. Li, L.W. Xue, Russ. J. Coord. Chem. 43, 389 (2017)

    Article  CAS  Google Scholar 

  27. A. Sigel, H. Sigel (eds.), Handbook on Metalloproteins (Marcel Dekker, New York, 2002)

  28. J.M. Tunney, J. McMaster, C.D. Garner, in Comprehensive Coordination Chemistry II, ed. by J.A. McCleverty, T.J. Meyer (Elsevier Perganion, Amsterdam, 2004)

  29. C.G. Young, in Encyclopedia of Inorganic Chemistry 2, ed. by R.B. King (Wiley, Chichester, 2005)

  30. C.J. Doonan, D.J. Nielsen, P.D. Smith, J.M. White, G.N. George, C.G. Young, J. Am. Chem. Soc. 128, 305 (2006)

    Article  CAS  Google Scholar 

  31. B.K. Burgess, in Metal Ions in Biology Series, Molybdenum Enzymes, ed. by T.G. Spiro (Wiley- Interscience, New York, 1985)

  32. H. Kargar, M. Bazrafshan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H.A. Rudbari, K.S. Munawar, M. Ashfaq, M.N. Tahir, Polyhedron 202, 115194 (2021)

  33. H. Kargar, P. Forootan, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H.A. Rudbari, K.S. Munawar, M. Ashfaq, M.N. Tahir, Inorg. Chim. Acta 523, 120414 (2021)

  34. R. Kia, H. Kargar, J. Coord. Chem. 68, 1441 (2015)

    Article  CAS  Google Scholar 

  35. C. Radunsky, J. Kosters, M.C. Letzel, S. Yogendra, C. Schwickert, S. Manck, B. Sarkar, R. Pottgen, J.J. Weigand, J. Neugebauer, J. Muller, Eur. J. Inorg. Chem. 2015, 4006 (2015)

    Article  CAS  Google Scholar 

  36. V. Mirkhani, S. Tangestaninejad, M. Moghadam, I. Mohammadpoor-Baltork, H. Kargar, J. Mol. Catal. A: Chem. 242, 251 (2005)

    Article  CAS  Google Scholar 

  37. M. Hatefi, M. Moghadam, I. Sheikhshoaei, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor-Baltork, H. Kargar, Appl. Catal. A: Gen. 370, 66 (2009)

    Article  CAS  Google Scholar 

  38. H. Kargar, Inorg. Chem. Commun. 14, 863 (2011)

    Article  CAS  Google Scholar 

  39. H. Kargar, Transition Met. Chem. 39, 811 (2014)

    Article  CAS  Google Scholar 

  40. G.J.J. Chen, J.W. McDonald, W.E. Newton, Inorg. Chem. 15, 2612 (1976)

    Article  CAS  Google Scholar 

  41. Stoe & Cie, X-AREA, version 1.30: Program for the acquisition and analysis data (Stoe & Cie GmbH, Darmatadt, 2005)

  42. R.H. Blessing, Acta Crystallogr. A 51, 33 (1995)

    Article  Google Scholar 

  43. A.L. Spek, Acta Crystallogr. D65, 148 (2009)

    Google Scholar 

  44. G.M. Sheldrick, Acta Crystallogr. A 64, 112 (2008)

    Article  CAS  Google Scholar 

  45. S.P. Gao, J. Coord. Chem. 64, 2869 (2011)

    Article  CAS  Google Scholar 

  46. Y.M. Cui, Y. Wang, Y.J. Cai, X.J. Long, W.J. Chen, Coord. Chem. 66, 2325 (2013)

    Article  CAS  Google Scholar 

  47. V. Vrdoljak, B. Prugovecki, D.M. Calogovic, J. Pisk, R. Dreos, P. Siega, Cryst. Growth Des. 11, 1244 (2011)

    Article  CAS  Google Scholar 

  48. M. Bagherzadeh, M. Amini, H. Parastar, M. Jalali-Heravi, A. Ellern, L.K. Woo, Inorg. Chem. Commun. 20, 86 (2012)

    Article  CAS  Google Scholar 

  49. A. Rana, R. Dinda, P. Sengupta, S. Ghosh, L.R. Falvello, Polyhedron 21, 1023 (2002)

    Article  CAS  Google Scholar 

  50. S. Gao, X.F. Zhang, L.H. Huo, H. Zhao, Acta Crystallogr. E60, m1731 (2004)

  51. V. Vrdoljak, M. Cindric, D. Milic, D. Matkovic-Calogovic, P. Novak, B. Kamenar, Polyhedron 24, 1717 (2005)

    Article  CAS  Google Scholar 

  52. M. Karman, M. Wera, G. Romanowski, Polyhedron 187, 114653 (2020)

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Acknowledgements

The author gratefully acknowledges practical support of this study by Ardakan University.

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

    Hadi Kargar

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Kargar, H. Molybdenum(VI) complexes with tridentate Schiff base ligands derived from isoniazid as catalysts for the oxidation of sulfides: synthesis, X-ray crystal structure determination and spectral characterization. J IRAN CHEM SOC 19, 967–977 (2022). https://doi.org/10.1007/s13738-021-02355-0

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