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Vol. 36 No. 3 (2024): Vol 36 Issue 3, 2024

Copyright (c) 2024 Kanti Ranjan Nath Bhowmik Kanti

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Synthesis, Structural Characterization, Reactivity and Bioactivity Studies of Some Binuclear Salen Type Schiff Base Complexes of Manganese(III)

https://doi.org/10.14233/ajchem.2024.31074
K.R. Nath Bhowmik Bhowmik
Department of Chemistry, Ramthakur College, Agartala-799002, India
https://orcid.org/0009-0005-0576-5920
R.N. Dutta Purkayastha
Department of Chemistry, Tripura University, Suryamaninagar-799022, India
https://orcid.org/0000-0001-6891-7630
S. Roy
Department of Chemistry, The ICFAI University Tripura, Kamalghat, Mohanpur, Agartala-799210, India
https://orcid.org/0000-0002-0097-6113

Corresponding Author(s) : K.R. Nath Bhowmik Bhowmik

kantinathbhowmik@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 3 (2024): Vol 36 Issue 3, 2024

Abstract

Four new phenoxy bridged binuclear Salen type Schiff base complexes of manganese(III), [MnLX]2 with tetradentate Schiff base, H2L [H2L = N,N′-O-phenylene bis(salicylaldimine)] containing anionic co-ligands, X (X = benzoate, p-hydroxy benzoate, p-aminobenzoate, 3,5-dinitrobenzoate) have been synthesized from manganese(II) acetate, Schiff base (H2L) and the corresponding co-ligands in methanol medium. Schiff base ligand (H2L) was obtained in situ by condensation of salicylaldehyde and o-phenylenediamine in aqueous methanol. Elemental analyses, FT-IR, molar conductance, UV-visible spectroscopic studies and magnetic moment measurements at room temperature were used to characterize the binuclear Schiff base complexes. The IR spectra of [MnLX]2 (X = benzoate, p-hydroxy benzoate, p-aminobenzoate, 3,5-dinitrobenzoate) complexes showed the characteristic absorptions due to coordinated azomethine nitrogen and phenolic oxygen atoms of the Schiff base. In addition, IR spectra of the compounds also suggest coordination of the co-ligands namely benzoate, p-hydroxy benzoate, p-aminobenzoate, 3,5-dinitrobenzoate in the respective complexes. A consistent presence of a band at ca. 755 cm-1 in all the binuclear complexes arises due to (Mn-O-Mn) moiety originated from interactions of phenoxy oxygen and manganese atoms, resulted in dimeric structure of the compounds. The magnetic moment values ranging from 4.74-4.91 B.M. per manganese centre for the complexes suggest presence of Mn(III) ion in the complexes. The overall coordination geometry around the manganese centres is distorted octahedral. Redox behaviour of the synthesized complexes was ascertained from cyclic voltametric studies. The Schiff base complexes, [Mn(L)X]2 (X = p-aminobenzoate, 3,5-dinitrobenzoate) have demonstrated their catalytic potentials in oxidizing selective organic substrates namely cyclohexene and styrene by hydrogen peroxide as oxidant. The oxidized products were characterized as trans-cyclohexane 1,2-diol and styrene epoxide, respectively. Complex 4 demonstrated a considerable level of effectiveness against a wide variety of pathogenic microorganisms.

Keywords

Mn(III) Schiff base complexes Synthesis Bioactivity study Reactivity
Bhowmik, K. N. B., Purkayastha, R. D., & Roy, S. (2024). Synthesis, Structural Characterization, Reactivity and Bioactivity Studies of Some Binuclear Salen Type Schiff Base Complexes of Manganese(III). Asian Journal of Chemistry, 36(3), 690–696. https://doi.org/10.14233/ajchem.2024.31074
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References
  1. P.G. Cozzi, Chem. Soc. Rev., 33, 410 (2004); https://doi.org/10.1039/B307853C
  2. M. Ohashi, T. Koshiyama, T. Ueno, M. Yanase, H. Fujii and Y. Watanabe, Angew. Chem. Int. Ed., 42, 1005 (2003); https://doi.org/10.1002/anie.200390256
  3. N. Yokoi, T. Ueno, M. Unno, T. Matsui, M. Ikeda-Saito and Y. Watanabe, Chem. Commun., 229 (2008); https://doi.org/10.1039/B713468A
  4. M. Marcos, J. L. Serrano, T. Sierra and M.J. Gimenez, Chem. Mater., 5, 1332 (1993); https://doi.org/10.1021/cm00033a025
  5. J.P. Costes, J.F. Lamère, C. Lepetit, P.G. Lacroix, F. Dahan and K. Nakatani, Inorg. Chem., 44, 1973 (2005); https://doi.org/10.1021/ic048578n
  6. N. Yoshida, K. Ichikawa and M. Shiro, J. Chem. Soc., Perkin Trans. 2, 17 (2000); https://doi.org/10.1039/A908041D
  7. M.S. Nair, D. Arish and R.S. Joseyphus, J. Saud. Chem. Soc., 16, 83 (2012); https://doi.org/10.1016/j.jscs.2010.11.002
  8. K.S. Kumar, S. Ganguly, R. Veerasamy and E. De Clercq, Eur. J. Med. Chem., 45, 5474 (2010); https://doi.org/10.1016/j.ejmech.2010.07.058
  9. N. Zhang, Y.-H. Fan, Z. Zhang, J. Zuo, P.-F. Zhang, Q. Wang, S.-B. Liu and C.-F. Bi, Inorg. Chem. Commun., 22, 68 (2012); https://doi.org/10.1016/j.inoche.2012.05.022
  10. S.J. Wezenberg and A.W. Kleij, Angew Chem., Int. Ed., 47, 2354 (2008); https://doi.org/10.1002/anie.200702468
  11. E.N. Jacobsen, in Eds.: I. Ojima, Catalytic Asymmetric Synthesis, VCH, Weinheim, p. 159 (1993).
  12. T. Katsuki, in Eds.: I. Ojima, Catalytic Asymmetric Synthesis, Wiley: New York, edn. 2, p. 287 (2000).
  13. S. Majumder, S. Hazra, S. Dutta, P. Biswas and S. Mohanta, Polyhedron, 28, 2473 (2009); https://doi.org/10.1016/j.poly.2009.04.034
  14. H. Miyasaka, R. Clérac, W. Wernsdorfer, L. Lecren, C. Bonhomme, K.-I. Sugiura and M. Yamashita, Angew. Chem., 116, 2861 (2004); https://doi.org/10.1002/anie.200353563
  15. H. Miyasaka, T. Nezu, K. Sugimoto, K.I. Sugiura, M. Yamashita and R. Clérac, Chem. Eur. J., 11, 1592 (2005); https://doi.org/10.1002/chem.200400946
  16. G. Bhargavi, M.V. Rajasekharan, J.P. Costes and J.P. Tuchagues, Polyhedron, 28, 1253 (2009); https://doi.org/10.1016/j.poly.2009.02.024
  17. G. Bhargavi, M.V. Rajasekharan and J.P. Tuchagues, Inorg. Chim. Acta, 362, 3247 (2009); https://doi.org/10.1016/j.ica.2009.02.032
  18. J. Nishijo, T. Yoshida and M. Enomoto, Polyhedron, 87, 233 (2015); https://doi.org/10.1016/j.poly.2014.11.015
  19. J.J.R. Frausto da Silva and R.J.P. Williams, The Biological Chemistry of the Elements. Oxford University Press (2001).
  20. V.L. Pecoraro, Manganese Radox Enzymes, VCH: New York (1992).
  21. M.S. Ray, R. Bhattacharya, L. Righi, G. Bocelli, G. Mukhopadhyay, S. Chaudhuri and A. Ghosh, Polyhedron, 22, 617 (2003); https://doi.org/10.1016/S0277-5387(02)01435-3
  22. S. Chattopadhyay, M. S. Ray, S. Chaudhuri, G. Mukhopadhyay, G. Bocelli, A. Cantoni and A. Ghosh, Inorg. Chim. Acta, 359, 1367 (2006); https://doi.org/10.1016/j.ica.2005.12.011
  23. M.S. Ray, A. Ghosh, R. Bhattacharya, G. Mukhopadhyay, M.G.B. Drew and J. Ribas, Dalton. Trans., 252 (2004); https://doi.org/10.1039/B311499F
  24. H.D. Bian, J.-Y. Xu, W. Gu, S.-P. Yan, P. Cheng, D.-Z. Liao and Z.-H. Jiang, Polyhedron, 22, 2927 (2003); https://doi.org/10.1016/S0277-5387(03)00395-4
  25. Q.-B. Li, Y.-J. Han, G.Q. Zhao and L.W. Xue, Acta. Chim. Slov., 64, 500 (2017); https://doi.org/10.17344/acsi.2017.3416
  26. C.T. Brewer and G. Brewer, J. Chem. Soc. Chem. Commun., 854 (1988); https://doi.org/10.1039/C39880000854
  27. M. Kwiatkowski, E. Kwiatkowski, A. Olechnowiez, D.M. Ho and E. Deutsch, J. Chem. Soc., Dalton Trans., 3063 (1990); https://doi.org/10.1039/DT9900003063
  28. R. Karmakar, C.R. Choudhury, G. Bravic, J.-P. Sutter and S. Mitra, Polyhedron, 23, 949 (2004); https://doi.org/10.1016/j.poly.2003.12.012
  29. L. Lecren, W. Wernsdorfer, Y. -G. Li, A. Vindigi, H. Miyasaka and R. Clerac, J. Am. Chem. Soc., 129, 5045 (2007); https://doi.org/10.1016/j.poly.2003.12.012
  30. S. Das, M. Das, S. Laha, K. Rajak, I. Choudhuri, N. Bhattacharjee, B. C. Samanta and T. Maity, J. Mol. Struct., 1263, 133214 (2022); https://doi.org/10.1016/j.molstruc.2022.133214
  31. P. Paul, K.R.N. Bhowmik, S. Roy, D. Deb, N. Das, M. Bhattacharjee, R.N.D. Purkayastha, L. Male, V. Mckee, R. Pallepogu, D. Maiti, A. Banza, A. Fontera and A.M. Kirillov, Polyhedron, 151, 407 (2018); https://doi.org/10.1016/j.poly.2018.05.043
  32. H. Miyasaka, A. Saitoh and S. Abe, Coord. Chem. Rev., 251, 2622 (2007); https://doi.org/10.1016/j.ccr.2007.07.028
  33. Z. Lu, M. Yuan, F. Pan, S. Gao, D. Zhang and D. Zhu, Inorg. Chem., 45, 3538 (2006); https://doi.org/10.1021/ic051648l
  34. Q. Wu, J.C.X. Zhou, J. R. Sun, M.F. Huang, X. Xu, T. Li and H. Tian, Crystals, 10, 334 (2020); https://doi.org/10.3390/cryst10040334
  35. H.H. Ko, J. H. Lim, H. C. Kim and C. S. Hong, Inorg. Chem., 45, 8847 (2006); https://doi.org/10.1021/ic061415+
  36. G. Bhargavi, M.V. Rajasekharan and J.-P. Tuchagues, Inorg. Chim. Acta, 362, 3247 (2009); https://doi.org/10.1016/j.ica.2009.02.032
  37. H. Miyasaka, K. Mizushima, S. Furukawa, K. Sugiura, T. Ishii and M. Yamashita, Mol. Cryst. Liq. Cryst., 379, 171 (2002); https://doi.org/10.1080/713738598
  38. H. Miyasaka, R. Clerac, R.T. Ishii, H. Chang, S. Kitagawa and M. Yamashita, J. Chem. Soc., Dalton Trans., 1528 (2002); https://doi.org/10.1039/B111094M
  39. H. Shyu, H. We and Y. Wang, Inorg. Chim. Acta., 290, 8 (1999); https://doi.org/10.1016/S0020-1693(99)00089-4
  40. L. Rigamonti, P. Zardi, S. Carlino, F. Demartin, C. Castellano, L. Pigani, A. Ponti, A. M. Ferretti and A. Pasini, Int. J. Mol. Sci., 21, 7882 (2020); https://doi.org/10.3390/ijms21217882
  41. A. Barry, in Eds: V. Lorian, Antibiotics in Laboratory Medicine, Williams and Wilkins, Baltimore, MD, USA, pp. 1–16 (1991).
  42. T. Rosu, M. Negoiu and S. Pasculescu, Eur. J. Med. Chem. 45, 774 (2010); https://doi.org/10.1016/j.ejmech.2009.10.034
  43. A.I. Vogel, A Textbook of Quantitative Inorganic Analysis, Longman Green and Co. Ltd., New York, edn. 3 (1964).
  44. S. Majumder, S. Hazra, S. Dutta, P. Biswas and S. Mohanta, Polyhedron, 28, 2473 (2009); https://doi.org/10.1016/j.poly.2009.04.034
  45. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience: London, edn. 2 (1986).
  46. V. Gomez, M. Corbella and G. Aullon, Inorg. Chem., 49, 1471 (2010); https://doi.org/10.1021/ic901719t
  47. J.G. Grasselli and W.M. Ritchey, Atlas of Spectral Data and Physical Constants for Organic Compounds’, CRC Press: Ohio, USA, vol. 3, p. 119, 263 (1973).
  48. W. Kemp, Organic Spectroscopy, Palgrave Publishers: New York, edn. 3, p. 210 (1991).
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