Skip to main content
SpringerLink
Log in

Synthetic, spectroscopic and thermal studies of some complexes of unsymmetrical Schiff base ligand

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

New unsymmetrical Schiff base ligand (H2L) is prepared via condensation of 2-hydroxy-5-methyl acetophenone, 2-hydroxy-5-chloro-3-nitro acetophenone and carbohydrazide in 1:1:1 ratio. Metal complexes of VO(IV), Cr(III), Mn(III), Fe(III), Zr(IV), MoO2(VI), WO2(VI) and UO2(VI) have been prepared. These complexes were characterized by elemental analysis, UV–Vis and IR spectroscopy and magnetic moment and thermogravimetric analysis. The purity of the ligand and the metal complexes is confirmed by microanalyses, while unsymmetrical nature of ligand was further corroborated by 1H NMR. All the complexes are air stable and insoluble in water and common organic solvents but fairly soluble in DMSO. The elemental analysis shows 1:1 metal to ligand stoichiometry for all the complexes. Thermal behaviour of the complexes was studied, the complexes were found to be quite stable and their thermal decomposition was generally via partially loss of the organic moiety and ended with respective metal oxide as a final product. Comparison of the IR spectrum of ligand and its metal complexes confirm that Schiff base behave as a dibasic tetradentate ligand towards the central metal ion with an ONNO donor sequence. The dc electrical conductivity is studied and data obtained obeyed the relation σ = σ 0 exp(−E a/kT) over the temperature range 40–130 °C. X-ray diffraction study of VO(IV) complex shows its crystalline nature with triclinic crystal system.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2

Similar content being viewed by others

References

  1. Nora H, Al-Sha A. Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a Schiff base hydrazone containing a quinoline moiety. Molecules. 2007;12:1080–91.

    Article  Google Scholar 

  2. Abdallah SM, Zayed MA, Mohamad GG. Synthesis and characterization of new tetradentate Schiff base and its coordination compounds of NOON donor atoms and their antibacterial and antifungal activity. Arab J Chem. 2010;3:103–13.

    Article  CAS  Google Scholar 

  3. Hamurcu F, Gunduzalp AB, Cete S, Erk B. The synthesis, characterization and antimicrobial activity of N,N′-bis(2-thiophenecarboxamido)-1,3-diaminopropane and N,N′-bis(2-furancarboxamido)-1,3-diaminopropane and their Cu(II), Zn(II), Co(III) complexes. Trans Met Chem. 2008;33:137–41.

    Article  CAS  Google Scholar 

  4. Cukurovali A, Yilmaz I, Ozmen H. Cobalt(II), copper(II), nickel(II) and zinc(II) complexes of two novel Schiff base ligands and their antimicrobial activity. Trans Met Chem. 2002;27:171–6.

    Article  CAS  Google Scholar 

  5. Masar MS, Gianneschi NC, Oleveri CG, Stern CL, Nguyen ST, Mirking CA. Allosterically regulated supramolecular catalysis of acyl transfer reactions for signal amplification and detection of small molecules. J Am Chem Soc. 2007;129:10149–58.

    Article  CAS  Google Scholar 

  6. Asadi M, Sepehrpour H, Mohammadi K. Tetradentate Schiff base ligands of 3,4-diaminobenzophenone: synthesis, characterization and thermodynamics of complex formation with Ni(II), Cu(II) and Zn(II) metal ions. J Serb Chem Soc. 2011;76:63–74.

    Article  CAS  Google Scholar 

  7. Seleem HS, El-shetary BA, Khalil SME, Shebl M. Potentiometric and spectrophotometric studies of the complexation of Schiff-base hydrazones containing the pyrimidine moiety. J Serb Chem Soc. 2003;68:729–48.

    Article  CAS  Google Scholar 

  8. He Z, He C, Wang Z, Gao E, Liu Y, Yan C. Self-assembly of molecular squares based on easy-to-prepare multidentate Schiff base ligands. Dalton Trans. 2004:502–04.

  9. Fleming JS, Psillakis E, Couchman SM, Jeffery JC, McCleverty JA, Ward MD. Complexes of the potentially hexadentate ligand bis{3-[6-(2,2′-bipyridyl)]pyrazol-1-yl}hydroborate with representative s-, p-, d- and f-block metal ions: factors promoting formation of mononuclear or double-helical dinuclear complexes. Dalton Trans. 1998:537–40.

  10. Xavier KO, Chako J, Yusuff KKM. Intrazeolite cobalt(II), nickel(II) and copper(II) complexes of 3-formylsalicylic acid for oxidation reactions. J Mol Catal A Chem. 2002;178:275–81.

    Article  CAS  Google Scholar 

  11. Khalil SME, El-Shafiy HFO. VO(IV), Fe(III), Co(II) and Cd(II) complexes of assymetric Schiff base ligands (N2O3) synthesis and spectroscopic study. Synth React Inorg Met Org Chem. 2000;30:1817–33.

    Article  CAS  Google Scholar 

  12. Chakraborty J, Samanta B, Pilet G, Mitra S. Synthesis structure and spectral characterisation of a hydrogen bonded polymeric manganese(III) Schiff base complex. Struct Chem. 2006;17:585–93.

    Article  CAS  Google Scholar 

  13. Christensen OT. Untersuchungen uber manganverbindungen. II. Manganiacetat und Alaune des Mangans. Z Anorg Allg Chem. 1901;27:321–23.

    Google Scholar 

  14. Pethe GB, Yaul AR, Devhade JB, Aswar AS. Synthesis and characterization of some chelate polymers of poly-Schiff base ligand. Der Pharma Chemica. 2010;2:301–8.

    CAS  Google Scholar 

  15. Badwaik VB, Aswar AS. Carbohydrazone polychelates: synthesis, physicochemical characterization, solid state conductance and biological studies. Russ J Inorg. 2009;54:1611–18.

    Google Scholar 

  16. Boghaei DM, Sabouncheib SJS, Rayatib S. Synthesis and reactivity of unsymmetrical Schiff base ligand towards Ni(II), Cu(II) and Pd(II). Synth React Inorg Met Org Chem. 2000;30:1535–45.

    Article  CAS  Google Scholar 

  17. Singh RV, Joshi SC, Dwivedi R. Synthesis and characterization of cobalt(II), nickel(II), copper(II), palladium(II) and dioxouranium(VI) complexes of the antipyrine Schiff base of 3-formylsalicylic acid. Phosphorus Sulfur Silicon Relat Elem. 2004;179:227–36.

    Article  CAS  Google Scholar 

  18. Ray A, Pilet G, Gomen-Garcia CJ, Mitra S. Designing dicyanamide bridged 1D molecular architecture from a mononuclear copper(II) Schiff base precursor: synthesis, structural variations and magnetic study. Polyhedron. 2009;28:511–20.

    Article  CAS  Google Scholar 

  19. Raman N, Sakthivel A, Raja JD, Rajasekaran K. Designing, structural elucidation and comparison of cleavage ability of metal complexes containing tetradentate Schiff bases. Russ J Inorg Chem. 2008;53:213–9.

    Google Scholar 

  20. Badwaik VB, Deshmukh RD, Aswar AS. Synthesis, structural, and biological studies of some bivalent metal ion complexes with the tridentate Schiff base ligand. Russ J Coord Chem. 2009;35:247–52.

    Article  CAS  Google Scholar 

  21. Kumar D, Syamal A, Singh AK. Synthesis and characterization of manganese(II), cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), iron(III), zirconium(IV), dioxo-molybdenum(VI) and dioxouranium(VI) coordination compounds of polystyrene-supported tridentate dibasic Schiff base derived from semicarbazide and 3-formylsalicylic acid. Indian J Chem. 2003;42A:280–6.

    CAS  Google Scholar 

  22. Maurya MR, Singh N. Dioxomolybdenum(VI) and dioxouranium(VI) complexes of tetradentate amidate ligands. Indian J Chem. 2004;43A:542–5.

    CAS  Google Scholar 

  23. Maurya MR, Singh DP, Varma SK. New dioxo uranium(VI) complexes of tetradentate Schiff bases derived from o-cresotic acid hydrazide and various aldehyde/ketone. Synth React Inorg Met Org Chem. 1989;19:923–30.

    Article  CAS  Google Scholar 

  24. Nag JK, Pal S, Sinha C. Synthesis and characterization of cobalt(II), nickel(II), copper(II), palladium(II) and dioxouranium(VI) complexes of the antipyrine Schiff base of 3-formylsalicylic acid. Trans Met Chem. 2005;30:523–8.

    Article  CAS  Google Scholar 

  25. Garg R, Fahmim N, Sigh RV. Spectral and biocidal studies of manganese(II), dioxomolebdenum(VI) and oxovanadium (V) complexes with monobasic bidendate Schiff base ligands. J Indian Chem Soc. 2009;86:670–8.

    CAS  Google Scholar 

  26. Maldhure AK, Aswar AS. Synthesis and characterization of nickel(II), cobalt(II), magnese(II), copper (II), iron (II)and chromium(II) complexes of unsymmetrical complexes of unsymmetrical salen type ligand and their application as catalysts for the oxidation of styrene. J Indian Chem Soc. 2009;86:697–702.

    CAS  Google Scholar 

  27. Nejo AA, Kolawole GA, Opoku AR, Wolowska J, Brien PO. Synthesis, characterization and preliminary insulin-enhancing studies of symmetrical tetradentate Schiff base complexes of oxovanadium(IV). Inorg Chim Acta. 2009;362:3993–4001.

    Article  CAS  Google Scholar 

  28. Grisenti DL, Smith MB, Fang L, Bishop N, Wagenknecnt PS. A convenient synthesis of isocyclam and [16]aneN4 and the photophysics of their dicyanochromium(III) complexes. Inorg Chim Acta. 2010;363:157–62.

    Article  CAS  Google Scholar 

  29. Modi CK, Patel IA, Thaker BT. Manganese(III) Schiff-base complexes involving heterocyclic β-diketone and diethylene triamine. J Coord Chem. 2008;61:3110–21.

    Article  CAS  Google Scholar 

  30. Duelund L, Hazell R, Mckenzie CJ, Nielsen LP, Toftlund H. Solid and solution state structures of mono- and di-nuclear iron(III) complexes of related hexadentate and pentadentate aminopyridyl ligands. J Chem Soc Dalton Trans. 2001; 152–54.

  31. Yaul AR, Dhande VV, Yaul SR, Aswar AS. Transition metal complexes containing tridendate hydrazone Schiff base: Synthesis characterisation and biological activity. J Indian Chem Soc. 2011;88:775–80.

    CAS  Google Scholar 

  32. EI-Wakiel NA. TG, DTA and electrical conductance properties of some Cu(II) and Mn(II) bisazodianils complexes. J Therm Anal Calorim. 2004;77:839–49.

    Article  Google Scholar 

  33. Sarkar S, Aydogdu Y, Dagdelen F, Bhaumik BB, Dey K. X-ray diffraction studies, thermal, electrical and optical properties of oxovanadium(IV) complexes with quadridentate Schiff bases. J Mater Chem Phys. 2004;88:357–63.

    Article  CAS  Google Scholar 

  34. Masoud MS, Merghany AE, Ramadan AM. Thermal studies of some purine compounds and their metal complexes. J Therm Anal Calorim. 2010;101:839–45.

    Article  CAS  Google Scholar 

  35. Yaul AR, Dhande VV, Suryawanshi NJ, Aswar AS. Synthesis, structural investigation and biological studies of some transition metal chelates of acid hydrazone. Polish J Chem. 2009;83:565–71.

    CAS  Google Scholar 

  36. Aswar AS, Yaul AR, Dhande VV. Synthesis, characterization, electrical and biological studies of VO(IV), MoO2(VI), WO2(VI), Th(IV) and UO2(VI) complexes with hydrazone ligand. Rev Roum Chim. 2010;55:537–42.

    Google Scholar 

  37. Modi CK, Patel AS, Thaker BT. Synthesis, spectral, magnetic and thermal studies of the complexes of CoII and Ni II with some bidentate and tridentate hydrazone ligands. EJ Chem. 2005;2:21–9.

    CAS  Google Scholar 

Download references

Acknowledgements

The authors wish to thank SAIF Chandigarh and CDRI Lucknow for recording elemental analyses, IR, NMR and electronic spectral analysis of the compounds. One of the authors (ARY) is thankful to University Grants Commission for providing financial assistance.

Author information

Authors and Affiliations

  1. Department of Chemistry, Sant Gadge Baba Amravati University, Amravati, 444602, Maharashtra, India

    Gaurav Pethe, Amit Yaul & Anand Aswar

Authors
  1. Gaurav Pethe
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amit Yaul
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anand Aswar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anand Aswar.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pethe, G., Yaul, A. & Aswar, A. Synthetic, spectroscopic and thermal studies of some complexes of unsymmetrical Schiff base ligand. J Therm Anal Calorim 107, 97–103 (2012). https://doi.org/10.1007/s10973-011-1847-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-011-1847-4

Keywords

Search

Navigation