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Synthesis, characterization, and X-ray crystal structures of copper(II) and nickel(II) complexes with two bis(thiosemicarbazone) ligands and investigation of their electrochemical behavior

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Abstract

Two new bis(thiosemicarbazone) ligands having a halogen substituent on the non-coordinating phenyl rings, namely 2-[1-(2-{3-[2-({2-[(4-bromoanilino)carbothioyl]hydrazono} methyl)phenoxy]propoxy}phenyl)methylidene]-N1-(4-bromophenyl)-1-hydrazinecarbothiamide (H 2 L3) and 2-[1-(2-{3-[2-({2-[(4-bromoanilino)carbothioyl]hydrazono}methyl)phenoxy]-2-hydroxypropoxy}phenyl) methylidene]-N1-(4-bromophenyl)-1-hydrazinecarbothiamide (H 3 L4), were used in the synthesis of a series of CuII and NiII complexes [Cu(L3)]·MeOH, [Cu(HL4)], [Ni(L3)], and [Ni(HL4)]·MeOH. The complexes were characterized by physicochemical and spectroscopic methods. Single-crystal X-ray structures of [Cu(L3)]·MeOH, [Cu(HL4)], and [Ni(L3)] showed that the metal centers are coordinated by two imine nitrogen atoms and two sulfur atoms in a distorted square-planar coordination geometry. Electrochemical investigations showed that all of these CuII and NiII complexes were reversibly reducible. Although the bromine substituent on the phenyl ring and the hydroxyl group are far from the metal centers, they have an effect on the redox potentials of the NiII/I and CuII/I couples.

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References

  1. West DX, Liberta AE (1993) Coord Chem Rev 123:49–71

    Article  CAS  Google Scholar 

  2. Lobana TS, Sharma R, Bawa G, Khanna S (2009) Coord Chem Rev 253:977–1055

    Article  CAS  Google Scholar 

  3. Fatondji HR, Kpoviessi S, Gbaguidi F, Bero J, Hannaert V, Quetin-Leclercq J, Poupaert J, Moudachirou M, Accrombessi GC (2013) Med Chem Res 22:2151–2162

    Article  CAS  Google Scholar 

  4. Maurer RI, Blower PJ, Dilworth JR, Reynolds CA, Zheng Y, Mullen GED (2002) J Med Chem 45:1420–1431

    Article  CAS  Google Scholar 

  5. Beckford FA, Thessing J, Stott A, Holder AA, Poluektov OG, Li L, Seeram NP (2012) Inorg Chem Commun 15:225–229

    Article  CAS  Google Scholar 

  6. Dearling JLJ, Lewis JS, Mullen GED, Welch MJ, Blower PJ (2002) J Biol Inorg Chem 7:249–259

    Article  CAS  Google Scholar 

  7. Zeglis BM, Divilov V, Lewis JS (2011) J Med Chem 54:2391–2398

    Article  CAS  Google Scholar 

  8. Hall MD, Brimacombe KR, Varonka MS, Pluchino KM, Monda JK, Li J, Walsh MJ, Boxer MB, Warren TH, Fales HM, Gottesman MM (2011) J Med Chem 54:5878–5889

    Article  CAS  Google Scholar 

  9. Stefani C, Punnia-Moorthy G, Lovejoy DB, Jansson PJ, Kalinowski DS, Sharpe PC, Bernhardt PV, Richardson DR (2011) J Med Chem 54:6936–6948

    Article  CAS  Google Scholar 

  10. Palanimuthu D, Shinde SV, Somasundaram K, Samuelson AG (2013) J Med Chem 56:722–734

    Article  CAS  Google Scholar 

  11. Cowley AR, Dilworth JR, Donnelly PS, Gee AD, Heslop JM (2004) Dalton Trans pp 2404–2412

  12. Santini C, Pellei M, Gandin V, Porchia M, Tisato F, Marzano C (2014) Chem Rev 114:815–862

    Article  CAS  Google Scholar 

  13. Hall LH, Miller MC, West DX (1997) Met-Based Drugs 4:89–95

    Article  CAS  Google Scholar 

  14. Price KA, Crouch PJ, Volitakis I, Paterson BM, Lim SC, Donnelly PS, White AR (2011) Inorg Chem 50:9594–9605

    Article  CAS  Google Scholar 

  15. Urackova ZD, Mendiola MA, Sevilla MT, Valent A (1999) Bioelectrochem Bioenerg 48:109–116

    Article  Google Scholar 

  16. Hosseini-Yazdi SA, Hosseinpour S, Khandar AA, Kassel WS, Piro NA (2015) Inorg Chim Acta 427:124–130

    Article  CAS  Google Scholar 

  17. Gattegno D, Giuliani AM (1974) Tetrahedron 30:701–704

    Article  CAS  Google Scholar 

  18. Mohan M, Agarawal A, Jha NK (1988) J Inorg Biochem 34:41–54

    Article  CAS  Google Scholar 

  19. Sreekanth A, Fun H-K, Kurup MRP (2005) J Mol Struct 737:61–67

    Article  CAS  Google Scholar 

  20. Latheef L, Kurup MRP (2008) Polyhedron 27:35–43

    Article  CAS  Google Scholar 

  21. Holland JP, Aigbirhio FI, Betts HM, Bonnitcha PD, Burke P, Christlieb M, Churchill GC, Cowley AR, Dilworth JR, Donnelly PS, Green JC, Peach JM, Vasudevan SR, Warren JE (2007) Inorg Chem 46:465–485

    Article  CAS  Google Scholar 

  22. Yang L, Powell DR, Houser RP (2007) Dalton Trans 955–964

  23. Alsop L, Cowley AR, Dilworth JR, Donnelly PS, Peach JM, Rider JT (2005) Inorg Chim Acta 358:2770–2780

    Article  CAS  Google Scholar 

  24. Lopez-Torres E, Mendiola M, Pastor CJ, Perez BS (2004) Inorg Chem 43:5222–5230

    Article  CAS  Google Scholar 

  25. Reynolds CA, King PM, Richards WG (1988) Nature 334:80–82

    Article  CAS  Google Scholar 

  26. Cowley AR, Dilworth JR, Donnelly PS, Labisbal E, Sousa A (2002) J Am Chem Soc 124:5270–5271

    Article  CAS  Google Scholar 

  27. Khandar AA, Hosseini-Yazdi SA (2003) Polyhedron 22:1481–1487

    Article  CAS  Google Scholar 

  28. Hosseini-Yazdi SA, Mirzaahmadi A, Samadzadeh-Aghdam P, Khandar AA, Mahmoudi G, Kassel WS, Dougherty WG (2014) Inorg Chim Acta 414:115–120

    Article  CAS  Google Scholar 

  29. Hosseini-Yazdi SA, Samadzadeh-Aghdam P, Mirzaahmadi A, Khandar AA, Mahmoudi G, Ruck M, Doert T, Balula SS, Cunha-Silva L (2014) Polyhedron 80:41–46

    Article  CAS  Google Scholar 

  30. Lukmantara AY, Kalinowski DS, Kumar N, Richardson DR (2013) Org Biomol Chem 11:6414–6425

    Article  CAS  Google Scholar 

  31. Sheldrick GM (2008) Acta Cryst A64:112–122

    Article  Google Scholar 

  32. Farrugia LJ (1997) J Appl Cryst 30:565

    Article  CAS  Google Scholar 

  33. Farrugia LJ (1999) J Appl Cryst 32:837–838

    Article  CAS  Google Scholar 

  34. Van Der Sluis P, Spek AL (1990) Acta Cryst A46:194–201

    Article  Google Scholar 

Download references

Acknowledgments

We would like to thank University of Tabriz for supporting this work.

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Authors and Affiliations

  1. Department of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, Tabriz, 51666-14766, Iran

    Seyed Abolfazl Hosseini-Yazdi, Sara Hosseinpour & Ali Akbar Khandar

  2. School of Chemistry and Bio-21 Institute, University of Melbourne, Parkville, VIC, Australia

    Jonathan White

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  1. Seyed Abolfazl Hosseini-Yazdi
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  2. Sara Hosseinpour
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  3. Ali Akbar Khandar
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  4. Jonathan White
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Correspondence to Seyed Abolfazl Hosseini-Yazdi.

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Hosseini-Yazdi, S.A., Hosseinpour, S., Khandar, A.A. et al. Synthesis, characterization, and X-ray crystal structures of copper(II) and nickel(II) complexes with two bis(thiosemicarbazone) ligands and investigation of their electrochemical behavior. Transition Met Chem 41, 65–75 (2016). https://doi.org/10.1007/s11243-015-9997-z

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  • DOI: https://doi.org/10.1007/s11243-015-9997-z

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