SpringerLink
Log in

Novel dioxomolybdenum complexes containing ONO-tridentate Schiff base ligands derived from 4-aminobenzohydrazide: synthesis, spectral characterization, and application as efficient homogeneous catalysts for selective sulfoxidation

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

Abstract

Novel dioxomolybdenum Schiff base complexes, [MoO2(Ln)(CH3OH)], were synthesized by the reaction of MoO2(acac)2 and ONO donor Schiff base ligands (H2Ln) derived by the condensation of 4-aminobenzohydrazide and substituted salicylaldehydes. The synthesized ligands and their complexes were characterized by various spectroscopic techniques like FT-IR, 1H NMR, 13C NMR, and elemental analysis (CHN). The geometries around the central metal atom in the complexes were suggested distorted octahedral. Moreover, the catalytic efficiency of the complexes was investigated by oxidizing the aryl and alkyl sulfides in the presence of tert-butyl hydroperoxide in 1,2-dichloroethane under reflux conditions. This method has numerous ascendancies, such as high yield, short reaction time, and excellent selectivity to produce corresponding sulfoxides without overoxidation to sulfones.

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

Access this article

Log in via an institution

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.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2

Similar content being viewed by others

References

  1. J. Devi, N. Batra, R. Malhotra, Spectrochim. Acta Part A 97, 397 (2012)

    Article  CAS  Google Scholar 

  2. M. Gupta, S. Sihag, A.K. Varshney, S. Varshney, J. Chem. 745101 (2013)

  3. E. Yousif, A. Majeed, K. Al-Sammarrae, N. Salih, J. Salimon, B. Abdullah, Arab. J. Chem. 10, S1639 (2017)

    Article  CAS  Google Scholar 

  4. H. 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 195, 114988 (2021)

    Article  CAS  Google Scholar 

  5. H. Kargar, R. Behjatmanesh-Ardakani, V. Torabi, A. Sarvian, Z. Kazemi, Z. Chavoshpour-Natanzi, V. Mirkhani, A. Sahraei, M.N. Tahir, M. Ashfaq, Inorg. Chim. Acta 514, 120004 (2021)

    Article  CAS  Google Scholar 

  6. R. Sudheer, M. Sithambaresan, N.R. Sajitha, E. Manoj, M.P. Kurup, Acta Crystallogr. E71, 702 (2015)

    Google Scholar 

  7. P.B. Sreeja, M.R.P. Kurup, A. Kishore, C. Jasmin, Polyhedron 23, 575 (2004)

    Article  CAS  Google Scholar 

  8. R.S. Nair, M. Kuriakose, V. Somasundaram, V. Shenoi, M.R.P. Kurup, P. Srinivas, Life Sci. 116, 90 (2014)

    Article  CAS  PubMed  Google Scholar 

  9. E.N. Nfor, A. Husian, F. Majoumo-Mbe, I.N. Njah, O.E. Offiong, S.A. Bourne, Polyhedron 63, 207 (2013)

    Article  CAS  Google Scholar 

  10. R. Pal, V. Kumar, A.K. Gupta, V. Beniwal, Med. Chem. Res. 23, 3327 (2014)

    Article  CAS  Google Scholar 

  11. M. Wu, D.D. Yang, H.W. Zheng, Q.F. Liang, J.B. Li, Y. Kang, S. Li, C. Jiao, X.J. Zheng, L.P. **, Dalton Trans. 50, 1507 (2021)

    Article  CAS  PubMed  Google Scholar 

  12. R.P. Bakale, G.N. Naik, C.V. Mangannavar, I.S. Muchchandi, I.N. Shcherbakov, C. Frampton, K.B. Gudasi, Eur. J. Med. Chem. 73, 38 (2014)

    Article  CAS  PubMed  Google Scholar 

  13. B. Türkkan, B. Sarıboğa, N. Sarıboğa, Transit. Met. Chem. 36, 679 (2011)

    Article  CAS  Google Scholar 

  14. D.M. Boghaei, S. Mohebi, J. Mol. Catal. A: Chem. 179, 41 (2002)

    Article  CAS  Google Scholar 

  15. P.G. Cozzi, Chem. Soc. Rev. 33, 410 (2004)

    Article  CAS  PubMed  Google Scholar 

  16. K.S. Munawar, S. Ali, M.N. Tahir, N. Khalid, Q. Abbas, I.Z. Qureshi, S. Hussain, M. Ashfaq, J. Coord. Chem. 73, 2275 (2020)

    Article  CAS  Google Scholar 

  17. R. Ramnauth, S. Al-Juaid, M. Motevalli, B.C. Parkin, A.C. Sullivan, Inorg. Chem. 43, 4072 (2004)

    Article  CAS  PubMed  Google Scholar 

  18. H. Li, J. Wu, X. Huang, G. Lu, J. Yang, X. Lu, Q. **ong, H. Zhang, ACS Nano 7, 10344 (2013)

    Article  CAS  PubMed  Google Scholar 

  19. C. Wang, M. Yu, A.F. Kyle, P. Jakubec, D.J. Dixon, R.R. Schrock, A.H. Hoveyda, Chem. Eur. J. 19, 2726 (2013)

    Article  CAS  PubMed  Google Scholar 

  20. K.C. MacLeod, P.L. Holland, Nat. Chem. 5, 559 (2013)

    Article  CAS  PubMed  Google Scholar 

  21. H. Sugimoto, S. Tatemoto, K. Toyota, K. Ashikari, M. Kubo, T. Ogura, S. Itoh, Chem. Commun. 49, 4358 (2013)

    Article  CAS  Google Scholar 

  22. H. Sugimoto, M. Sato, L.J. Giles, K. Asano, T. Suzuki, M.L. Kirk, S. Itoh, Dalton Trans. 42, 15927 (2013)

    Article  CAS  PubMed  Google Scholar 

  23. M.E. Judmaier, C.H. Sala, F. Belaj, M. Volpe, N.C. Mösch-Zanetti, New J. Chem. 37, 2139 (2013)

    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. M.R. Maurya, M. Kumar, S.J.J. Titinchi, H.S. Abbo, S. Chand, Catal. Lett. 86, 97 (2003)

    Article  CAS  Google Scholar 

  26. T.A. Alsalim, J.S. Hadi, E.A. Al-Nasir, H.S. Abbo, S.J.J. Titinchi, Catal. Lett. 136, 228 (2010)

    Article  CAS  Google Scholar 

  27. A.P. de Azevedo Marques, E.R. Dockal, F.C. Skrobot, I.L.V. Rosa, Inorg. Chem. Commun. 10, 255 (2007)

    Article  CAS  Google Scholar 

  28. S. Bunce, R.J. Cross, L.J. Farrugia, S. Kunchandy, L.L. Meason, K.W. Muir, M. O’Donnel, R.D. Peacock, D. Stirling, S.J. Teat, Polyhedron 17, 4179 (1998)

    Article  CAS  Google Scholar 

  29. K.S. Munawar, S. Ali, M.N. Tahir, N. Khalid, Q. Abbas, I. Qureshi, S. Shahzadi, Russ. J. Gen. Chem. 85, 2183 (2015)

    Article  CAS  Google Scholar 

  30. R.S. Walmsley, Z.R. Tshentu, S. Afr, J. Chem. 63, 95 (2010)

    Google Scholar 

  31. S. Mohebbi, F. Nikpour, S. Raiati, J. Mol. Catal. A: Chem. 256, 265 (2006)

    Article  CAS  Google Scholar 

  32. M.M. Cecchini, F. De Angelis, C. Iacobucci, S. Reale, M. Crucianelli, Appl. Catal. A: Gen. 599, 117622 (2020)

    Article  CAS  Google Scholar 

  33. M. Mancka, W. Plass, Inorg. Chem. Commun. 10, 677 (2007)

    Article  CAS  Google Scholar 

  34. M. Salavati-Niasari, M. Bazarganipour, J. Mol. Catal. A: Chem. 278, 173 (2007)

    Article  CAS  Google Scholar 

  35. Y.D. Li, X.K. Fu, B.W. Gong, X.C. Zou, X.B. Tu, J.X. Chen, J. Mol. Catal. A: Chem. 322, 55 (2010)

    Article  CAS  Google Scholar 

  36. Y. Yang, Y. Zhang, S.J. Hao, Q.B. Kan, J. Colloid Interface Sci. 362, 157 (2011)

    Article  CAS  PubMed  Google Scholar 

  37. S.M. Bruno, J.A. Fernandes, L.S. Martins, I.S. Goncalves, M. Pillinger, P. Ribeiro-Claro, J. Rocha, A.A. Valente, Catal. Today 114, 263 (2006)

    Article  CAS  Google Scholar 

  38. C.Y. Lorber, S.P. Smidt, J.A. Osborn, Eur. J. Inorg. Chem. 655 (2000)

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

    Article  CAS  PubMed  Google Scholar 

  40. A.M. Khenkin, R. Neumann, J. Am. Chem. Soc. 124, 4198 (2002)

    Article  CAS  PubMed  Google Scholar 

  41. N. Baig, V.K. Madduluri, A.K. Sah, RSC Adv. 6, 28015 (2016)

    Article  CAS  Google Scholar 

  42. D.H. Hua, in Advances in Carbanion Chemistry, ed. by V. Snieckus (JAI Press, London, 1992)

  43. P. Renaud, M. Gerster, Angew. Chem. Int. Ed. 37, 2562 (1998)

    Article  CAS  Google Scholar 

  44. Y.Z. Wang, P. Wang, C. Li, Y.Q. Su, Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 46, 927 (2016)

    Article  CAS  Google Scholar 

  45. P. Suresh, S. Srimurugan, B. Babu, H.N. Pati, Tetrahedron Asymmetry 18, 2820 (2007)

    Article  CAS  Google Scholar 

  46. R.D. Chakravarthy, K. Suresh, V. Ramkumar, D.K. Chand, Inorg. Chim. Acta 376, 57 (2011)

    Article  CAS  Google Scholar 

  47. M.M. Javadi, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, J. Iran. Chem. Soc. 12, 477 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. W. Sheng, J.-L. Shi, H. Hao, X. Li, X. Lang, J. Colloid Interface Sci. 565, 614 (2020)

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  53. A. Sahraei, H. Kargar, M. Hakimi, M.N. Tahir, J. Mol. Struct. 1149, 576 (2017)

    Article  CAS  Google Scholar 

  54. A.A. Ardakani, H. Kargar, N. Feizi, M.N. Tahir, J. Iran. Chem. Soc. 15, 1495 (2018)

    Article  CAS  Google Scholar 

  55. H. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, M.N. Tahir, J. Iran. Chem. Soc. 16, 1081 (2019)

    Article  CAS  Google Scholar 

  56. H. Kargar, V. Torabi, A. Akbari, R. Behjatmanesh-Ardakani, A. Sahraei, M.N. Tahir, J. Mol. Struct. 1205, 127642 (2020)

    Article  CAS  Google Scholar 

  57. H. Kargar, F. Aghaei-Meybodi, R. Behjatmanesh-Ardakani, M.R. Elahifard, V. Torabi, M. Fallah-Mehrjardi, M.N. Tahir, M. Ashfaq, K.S. Munawar, J. Mol. Struct. 1230, 129908 (2021)

    Article  CAS  Google Scholar 

  58. H. Kargar, A.A. Ardakani, M.N. Tahir, M. Ashfaq, K.S. Munawar, J. Mol. Struct. 1229, 129842 (2021)

    Article  CAS  Google Scholar 

  59. H. Kargar, A.A. Ardakani, K.S. Munawar, M. Ashfaq, M.N. Tahir, J. Iran. Chem. Soc. (2021). https://doi.org/10.1007/s13738-021-02207-x

    Article  Google Scholar 

  60. A.K. Singh, O.P. Pandey, S.K. Sengupta, Spectrochim. Acta Part A 85, 1 (2012)

    Article  CAS  Google Scholar 

  61. S. Durmus, A. Atahan, M. Zengin, Spectrochim. Acta Part A 84, 1 (2011)

    Article  CAS  Google Scholar 

  62. A.H. Kianfar, M. Paliz, M. Roushani, M. Shamsipur, Spectrochim. Acta Part A 127, 422 (2014)

    Article  CAS  Google Scholar 

  63. M. Shebl, Spectrochim. Acta Part A 70, 850 (2008)

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  67. T.M. Asha, M.R.P. Kurup, J. Chem. Crystallogr. 49, 219 (2019)

    Article  CAS  Google Scholar 

  68. F. Ruff, A. Fabian, O. Farkas, A. Kucsman, Eur. J. Org. Chem. 2102 (2009)

  69. B. Yadollahi, Chem. Lett. 32, 1066 (2003)

    Article  CAS  Google Scholar 

  70. R. Tan, C. Li, Z. Peng, D. Yin, D. Yin, Catal. Commun. 12, 1488 (2011)

    Article  CAS  Google Scholar 

  71. S. Hussain, D. Talukdar, S.K. Bharadwaj, M.K. Chaudhuri, Tetrahedron Lett. 53, 6512 (2012)

    Article  CAS  Google Scholar 

  72. M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, Appl. Organomet. Chem. 29, 328 (2015)

    Article  CAS  Google Scholar 

  73. M. Bagherzadeh, M. Bahjati, A. Mortazavi-Manesh, J. Organomet. Chem. 897, 200 (2019)

    Article  CAS  Google Scholar 

  74. A. Ghorbani-Choghamarani, B. Ghasemi, Z. Safari, G. Azadi, Catal. Commun. 60, 70 (2015)

    Article  CAS  Google Scholar 

  75. H. Taghiyar, B. Yadollahi, Sci. Total Environ. 708, 134860 (2020)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge practical support of this study by Ardakan University and Payame Noor University.

Author information

Authors and Affiliations

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

    Hadi Kargar

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

    Mehdi Fallah-Mehrjardi

Authors
  1. Hadi Kargar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mehdi Fallah-Mehrjardi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hadi Kargar.

Ethics declarations

Conflict of interest

No potential conflict of interest was reported by the authors.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 5891 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kargar, H., Fallah-Mehrjardi, M. Novel dioxomolybdenum complexes containing ONO-tridentate Schiff base ligands derived from 4-aminobenzohydrazide: synthesis, spectral characterization, and application as efficient homogeneous catalysts for selective sulfoxidation. J IRAN CHEM SOC 18, 3443–3456 (2021). https://doi.org/10.1007/s13738-021-02282-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-021-02282-0

Keywords

Search

Navigation