Log in

Novel oxo–peroxo W(VI) Schiff base complex: synthesis, SC-XRD, spectral characterization, supporting on chloromethylated polystyrene, and catalytic oxidation of sulfides

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A novel oxo–peroxo tungsten(VI) Schiff base complex, [WO(O2)L(CH3OH)], as a homogeneous catalyst for sulfoxidation was synthesized by treating WO3 in H2O2 with an ONO–tridentate Schiff base ligand. The complex was characterized by FT-IR, UV–Vis, 1H NMR and 13C{1H} NMR spectroscopy. Moreover, the structure of the crystalline tungsten(VI) complex was further investigated by SC-XRD. The crystal structure analysis revealed that the coordination environment of the W complex is seven-coordinate, occupied by ONO sets of the coordinated ligand in a distorted pentagonal–bipyramidal. Also, the immobilized W(VI) Schiff base on chloromethylated polystyrene, showed high efficiency in the oxidation of the sulfide under heterogeneous conditions. The heterogeneous catalyst was systematically characterized by FT-IR, diffuse reflectance UV–Vis, XRD, FE-SEM, EDX, and ICP–AES techniques. Comparatively, the immobilized heterogeneous catalyst showed superior activity over its homogeneous counterpart and was reused several times.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (France)

Instant access to the full article PDF.

Scheme 1.
Scheme 2.
Fig. 1
Scheme 3.
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 4.

Similar content being viewed by others

References

  1. T. Katsuki, Coord. Chem. Rev. 140, 189 (1995)

    Article  CAS  Google Scholar 

  2. G. Licini, V. Conte, A. Coletti, M. Mba, C. Zonta, Coord. Chem. Rev. 255, 2345 (2011)

    Article  CAS  Google Scholar 

  3. C. Bolm, Coord. Chem. Rev. 237, 245 (2003)

    Article  CAS  Google Scholar 

  4. M. Amini, M.M. Haghdoost, M. Bagherzadeh, Coord. Chem. Rev. 268, 83 (2014)

    Article  CAS  Google Scholar 

  5. M. Bagherzadeh, M. Amini, A. Ellern, L.K. Woo, Inorg. Chem. Commun. 15, 52 (2012)

    Article  CAS  Google Scholar 

  6. M. Bagherzadeh, M. Zare, V. Amani, A. Ellern, L.K. Woo, Polyhedron 53, 223 (2013)

    Article  CAS  Google Scholar 

  7. S.K. Maiti, K.M.A. Malik, S. Gupta, S. Chakraborty, A.K. Ganguli, A.K. Mukherjee, R. Bhattacharyya, Inorg. Chem. 45, 9843 (2006)

    Article  CAS  PubMed  Google Scholar 

  8. R. Curci, J.O. Edwards, in Catalytic Oxidations with Hydrogen Peroxide as Oxidant, vol. 97 ed. by G. Strukul (Kluwer, Dordrecht, 1992)

  9. J.A.L. da Silva, J.J.R.F. da Silva, A.J.L. Pombeiro, Coord. Chem. Rev. 255, 2232 (2011)

    Article  CAS  Google Scholar 

  10. M.L. Ramos, L.L.G. Justino, H.D. Burrows, Dalton Trans. 40, 4374 (2011)

    Article  CAS  PubMed  Google Scholar 

  11. N. Mizuno, K. Yamaguchi, K. Kamata, Y. Nakagawa, in Activation of Hydrogen Peroxide by Polyoxometalates (Mechanism in Homogeneous and Heterogeneous Catalytic Epoxidation) ed by T. Oyama (Elsevier, Amsterdam, 155, 2008)

  12. B.S. Lane, K. Burgess, Chem. Rev. 103, 2457 (2003)

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. M. Amini, M. Bagherzadeh, Z. Moradi-Shoeili, D.M. Boghaei, A. Ellern, L.K. Woo, J. Coord. Chem. 66, 464 (2013)

    Article  CAS  Google Scholar 

  15. M.A. Fascione, S.J. Adshead, P.K. Mandal, C.A. Kilner, A.G. Leach, W.B. Turnbull, Chem. Eur. J. 18, 2987 (2012)

    Article  CAS  PubMed  Google Scholar 

  16. N. Gharah, S. Chakraborty, A.K. Mukherjee, R. Bhattacharyya, Inorg. Chim. Acta 362, 1089 (2009)

    Article  CAS  Google Scholar 

  17. S.K. Maiti, S. Dinda, S. Banerjee, A.K. Mukherjee, R. Bhattacharyya, Eur. J. Inorg. Chem. 2008, 2038 (2008)

    Article  CAS  Google Scholar 

  18. M. Bagherzadeh, P. Esmailpour, A. Abbasi, A. Akbari, M. Amini, J. Coord. Chem. 71, 3405 (2018)

    Article  CAS  Google Scholar 

  19. L.E. Bevers, P.L. Hagedoorn, W.R. Hagen, Coord. Chem. Rev. 253, 269 (2009)

    Article  CAS  Google Scholar 

  20. S.M. Islam, A.S. Roy, P. Mondal, K. Tuhina, M. Mobarak, J. Mondal, Tetrahedron Lett. 53, 127 (2012)

    Article  CAS  Google Scholar 

  21. J.P. Colman, L.S. Hegedus, J.R. Norton, R.G. Finkle, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, USA, 1987. D. Cole, J. Hamiltone, Science 299, 1702 (2003)

  22. S.J. Shuttleworth, S.M. Allin, R.D. Wilson, D. Nasturica, Synthesis 1035 (2000)

  23. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longhottom, M. Nesi, J.S. Scott, R. Storer, S.J. Taylor, J. Chem. Soc. Perkin Trans. 1, 3815 (2000)

    Article  Google Scholar 

  24. D.C. Sherrington, Catal. Today 57, 81 (2000)

    Article  Google Scholar 

  25. H. Deleuze, X. Schultze, D.C. Sherrington, J. Mol. Catal. A: Chem. 159, 257 (2000)

    Article  CAS  Google Scholar 

  26. N.E. Leadbeater, M. Marco, Chem. Rev. 102, 3217 (2002)

    Article  CAS  PubMed  Google Scholar 

  27. H.U. Blaser, B. Pugin, F. Spinder, J. Mol. Catal. A: Chem. 231, 1 (2005)

    Article  CAS  Google Scholar 

  28. C. Ren, X. Zhu, N. Zhao, S. Fang, Z. Li, Polymer 204, 122797 (2020)

    Article  CAS  Google Scholar 

  29. J. Lu, P.H. Toy, Chem. Rev. 109, 815 (2009)

    Article  CAS  PubMed  Google Scholar 

  30. S. Shanmugam, S. Xu, N.N.M. Adnan, C. Boyer, Macromolecules 51, 779 (2018)

    Article  CAS  Google Scholar 

  31. C.J. Whiteoak, A.H. Henseler, C. Ayats, A.W. Kleij, M.A. Pericas, Green Chem. 16, 1552 (2014)

    Article  CAS  Google Scholar 

  32. G.R. Krishnan, K. Sreekumar, Eur. J. Org. Chem. 28, 4763 (2008)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  34. 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 

  35. M. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor-Baltork, H. Kargar, I. Sheikhshoaei, M. Hatefi, J. Iran. Chem. Soc. 8, 1019 (2011)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. H. Kargar, Transit. Met. Chem. 39, 811 (2014)

    Article  CAS  Google Scholar 

  38. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Transit. Met. Chem. 46, 437 (2021)

    Article  CAS  Google Scholar 

  39. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Polyhedron 208, 115428 (2021)

    Article  CAS  Google Scholar 

  40. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Inorg. Chim. Acta 526, 120535 (2021)

    Article  CAS  Google Scholar 

  41. H. Kargar, A. Kaka-Naeini, M. Fallah-Mehrjardi, R. Behjatmanesh Ardakani, H. AmiriRudbari, K.S. Munawar, J. Coord. Chem. 74, 1563 (2021)

    Article  CAS  Google Scholar 

  42. H. Kargar, M. Fallah-Mehrjardi, J. Iran. Chem. Soc. 18, 3443 (2021)

    Article  CAS  Google Scholar 

  43. H. Kargar, J. Iran. Chem. Soc. (2021). https://doi.org/10.1007/s13738-021-02355-0

    Article  Google Scholar 

  44. H. Kargar, A. Moghimi, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H.A. Rudbari, K.S. Munawar, J. Sulfur Chem. (2021). https://doi.org/10.1080/17415993.2021.1941020

    Article  Google Scholar 

  45. 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)

    Article  CAS  Google Scholar 

  46. 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)

    Article  CAS  Google Scholar 

  47. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, Inorg. Chim. Acta 527, 120568 (2021)

    Article  CAS  Google Scholar 

  48. H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K.S. Munawar, J. Mol. Struct. 1245, 131259 (2021)

    Article  CAS  Google Scholar 

  49. M. Fallah-Mehrjardi, H. Kargar, Inorg. Chem. Commun. 134, 109016 (2021)

    Article  CAS  Google Scholar 

  50. H. Kargar, M. Nateghi-Jahromi, M. Fallah-Mehrjardi, R. Behjatmanesh Ardakani, K.S. Munawar, S. Ali, M. Ashfaq, M.N. Tahir, J. Mol. Struct. 1249, 131645 (2022)

    Article  CAS  Google Scholar 

  51. X–AREA, version 1.30, program for the acquisition and analysis of data, Stoe & Cie GmbH, Darmstadt, Germany, (2005)

  52. X–RED, version 1.28b, program for data reduction and absorption correction, Stoe & Cie GmbH, Darmstadt, Germany, (2005)

  53. X–SHAPE, version 2.05, program for crystal optimization for numerical absorption correction, Stoe & Cie GmbH, Darmstadt, Germany, (2004)

  54. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 38, 381 (2005)

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  56. A.D. Westland, F. Haque, J.M. Bouchard, Inorg. Chem. 19, 2255 (1980)

    Article  CAS  Google Scholar 

  57. H. Oku, N. Ueyama, A. Nakamura, Inorg. Chem. 34, 3667 (1995)

    Article  CAS  Google Scholar 

  58. Y. Ishii, H. Tanaka, Y. Nisiyama, Chem. Lett. 1 (1994)

  59. Z. Stec, J. Zawadiak, A. Skibinski, G. Pastuch, Polish J. Chem. 70, 1121 (1996)

    CAS  Google Scholar 

  60. R. Neumann, D. Juwiler, Tetrahedron 52, 8781 (1996)

    Article  CAS  Google Scholar 

  61. F.M. Collins, A.R. Lucy, C. Sharp, J. Mol. Catal. A: Chem. 117, 397 (1997)

    Article  CAS  Google Scholar 

  62. N. Noshiranzadeh, M. Mayeli, R. Bikas, K. S ́lepokura, T. Lis, Transit. Met. Chem. 39, 33 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The support of this work by Ardakan University, Isfahan University, and Payame Noor University is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Hadi Kargar or Majid Moghadam.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1255 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kargar, H., Moghadam, M., Shariati, L. et al. Novel oxo–peroxo W(VI) Schiff base complex: synthesis, SC-XRD, spectral characterization, supporting on chloromethylated polystyrene, and catalytic oxidation of sulfides. J IRAN CHEM SOC 19, 3067–3077 (2022). https://doi.org/10.1007/s13738-022-02517-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-022-02517-8

Keywords

Navigation