Skip to main content
Log in

Thermal and spectral studies of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes with 3-(anilinomethylene)-2-methoxychroman-4-one

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

Abstract

The complexes Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) with 3-(anilinomethylene)-2-methoxychroman-4-one were synthesized and characterized by elemental analysis, conductivity, infrared and UV–Vis spectroscopy, 1H NMR, X-ray diffraction patterns, magnetic susceptibility and thermal analysis (TG/DTG/DSC). The X-ray analysis shows that the studied compounds crystallize in the triclinic crystal system and they are no isostructural complexes. The unit cell parameters for these chelates were presented. The molecules of solvent are in the outside coordination sphere of the complexes. The chelates have different thermal stability and they decompose in air atmosphere in three steps. The coordination of metal ions is through nitrogen atom from ligand and oxygen atom present in 4-position of γ-pyrone. The studied chelates have electrolyte (1:1) and non-electrolyte nature. They are high-spin complexes with octahedral coordination and the weak ligand fields.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Wang BD, Yang ZY, Lu MH, Hai J, Wang Q, Chen ZN. Synthesis, characterization, cytotoxic activity and DNA binding Ni(II) complex with the 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone. J Org Chem. 2009;694:4069–75.

    Article  CAS  Google Scholar 

  2. Rybarczyk-Pirek AJ, Małecka M, Grabowski SJ, Nawrot-Modranka J. A benzopyran derivative substituted at position 3. Acta Cryst. 2002;C58:405–6.

    Google Scholar 

  3. Wang BD, Yang ZY, Li TR. Synthesis, characterization, and DNA- binding properties of the Ln(III) complexes with 6-hydroxy chromone-3-carbaldehyde-(2’-hydroxy) benzoyl hydrazone. Bioorg Med Chem. 2006;14:6012–21.

    Article  CAS  Google Scholar 

  4. Nawrot-Modranka J, Nawrot E, Graczyk J. In vivo antitumor, in vitro antibacterial activity and alkylating properties of phosphorohydrazine derivaties of coumarin and chromone. Eur J Med Chem. 2006;41:1301–9.

    Article  CAS  Google Scholar 

  5. Singh G, Singh R, Girdhar NK, Ishar MPS. A versatile route to 2-alkyl-/aryl-amino-3-formyl-and heteroannelated-chromones, through a facile nucleophilic substitution at C2 in 2-(N-methylanilino)-3-formylchromones. Tetrahedron. 2002;58:2471–80.

    Article  CAS  Google Scholar 

  6. Loa J, Chow P, Zhang K. Studies of structure-activity relationship on plant polyphenol-induced suppression of human liver cancer cells. Cancer Chemother Pharmacol. 2009;63:1007–16.

    Article  CAS  Google Scholar 

  7. Agosthina M, Matos R, Sousa C, Morais V. Thermochemistry of chromone and coumarin-3-carboxylic acid. J Therm Anal Calorim. 2010;100:519–26.

    Article  Google Scholar 

  8. Shim YS, Kim KCh, Chi DY, Lee KH, Cho H. Formylchromone derivatives as a novel class of protein tyrosine phosphatase 1B inhibitors. Bioorg Med Chem Lett. 2003;13:2561–3.

    Article  CAS  Google Scholar 

  9. Arjunan V, Subramanian S, Mohan S. FTIR and FTR spectral studies of 2-amino-6-bromo -3-fromylchromone. Spectrochim Acta. 2004;A60:995–1000.

    Google Scholar 

  10. Stankovicova H, Lacova M, Gaplovsky A, Chavanova J, Pranayova N. Reaction of 3-formylchromones with aromatic amino carboxylic acids. Tetrahedron. 2001;57:3455–64.

    Article  CAS  Google Scholar 

  11. Plaskon AS, Ryabukhin SV, Volochnyuk DM, Gavrilenko KS, Shivanyuk AN, Tolmachev AA. Synthesis of quinolines from 3-formylchromone. J Org Chem. 2008;73:6010–3.

    Article  CAS  Google Scholar 

  12. Bondyopadhyay Ch, Sur KR, Patra R, Sen A. Synthesis of coumarin derivatives from 4-oxo-4H–1-benzopyran-3-carboxaldehyde via 3-(arylaminomethylene)chroman-2,4-dione. Tetrahedron. 2000;56:3583–7.

    Article  Google Scholar 

  13. Borrell JI, Teixido J, Schuler E, Michelotti E. Solid-supported synthetic eguivalents of 3-formylchromone and chromone. Tetrahedron Lett. 2001;42:5331–4.

    Article  CAS  Google Scholar 

  14. Sasnovskikh VY, Moshkin VS, Irgashev RA. The first synthesis of 3-cyano-2-(polyfluoroalkyl)chromones. Tetrahedron Lett. 2006;47:8543–6.

    Article  Google Scholar 

  15. El-Shaaer HM, Foltinova P, Lacova M, Chovancova J, Stankovicova H. Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4-oxo-4H-benzopyran-3-carboxaldehydes with aminobenzothiazoles and hydrazides. II Farmaco. 1998;53:224–32.

    Article  CAS  Google Scholar 

  16. Dziewulska-Kułaczkowska A, Mazur L. Structural studies and characterization of 3-formylchromone and products of its reactions with chosen primary aromatic amines. J Mol Struct. 2010;985:233–42.

    Article  Google Scholar 

  17. Werner PE. TREOR, trial and error program for indexing of unknown powder patterns, University of Stockholm, Stockholm: Sweden; 1984. p. S106 91.

  18. König E. Magnetic properties of coordination and organometallic transition metal compounds. Berlin: Springer Verlag; 1966.

    Google Scholar 

  19. Socrates G. Infrared and Raman characteristic group frequencies. Chichester: Wiley; 2001.

    Google Scholar 

  20. Nakamoto K. Infrared and Raman spectra of inorganic and coordination compounds. Toronto: Wiley; 1997.

    Google Scholar 

  21. El-Boraey HA, Donia AM, El-Samalehy MF. Preparation, characterization and thermal investigation of polymeric and monomeric binuclear complexes of dianils derived from 6-formylkhellin with cobalt(II), nickel(II) and copper(II). J Anal Appl Pyrolysis. 2005;73:204–11.

    Article  CAS  Google Scholar 

  22. Pajtášová M, Ondrušová D, Jóna E, Mojumdar SC, L’alíková S, Bazyláková T, Gregor M. Spectral and thermal characteristic of copper(II) carboxylates with fatty acid chains and their benzothiazole adducts. J Therm Anal Calorim. 2010;100:769–77.

    Article  Google Scholar 

  23. Ahmed IS, El-Mossalamy EH. Synthesis and characterization of oxazolone complexes with Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) in different counterions. J Anal Appl Pyrolysis. 2003;70:679–86.

    Article  CAS  Google Scholar 

  24. Sönmez M, Levent A, Sekerci M. Synthesis, characterization, and thermal investigation of some metal complexes containing polydentate ONO-donor heterocyclic Schiff base ligand. Russ J Coord Chem. 2004;30(9):655–60.

    Article  Google Scholar 

  25. Dziewulska-Kułaczkowska A. Manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) complexes with 4-oxo-4H–1-benzopyran-3-carboxaldehyde. Thermal, spectroscopic and magnetic characterization. J Therm Anal Calorim. 2010;101:1019–26.

    Article  Google Scholar 

  26. Rzączyńska Z, Sienkiewicz-Gromiuk J, Głuchowska H. Structural and thermal properties of rare earth complexes with 2, 2′-biphenyldicarboxylic acid. J Therm Anal Calorim. 2010;101:213–9.

    Article  Google Scholar 

  27. Nikolaev AV, Logvinienko VA, Myachina LI. Thermal analysis. New York: Academic Press; 1989.

    Google Scholar 

  28. Paulik F. Special trends in thermal analysis. Chichester: Wiley; 1995.

    Google Scholar 

  29. Todor DN. Thermal Analysis of Minerals. Kent: Abacus Press, Tunbridge Wells; 1976.

    Google Scholar 

  30. Šumar-Ristović MT, Minić DM, Poleti D, Miodragović Z, Miodragović D, Andelković KK. Thermal stability degradation of Co(II), Cd(II) and Zn(II) complexes with N-benzyloxycarbonylglycinato ligand. J Therm Anal Calorim. 2010;102:83–90.

    Article  Google Scholar 

  31. Chen S-P, Li N, Wei Q, Gao S-L. Synthesis, structure analysis and thermodynamics of [Ni(H2O4(TO)2](NO3)2·2H2O (TO = 1,2,4-triazole-5-one). J Therm Anal Calorim. 2010;100:1115–20.

    Article  CAS  Google Scholar 

  32. Dziewulska-Kułaczkowska A, Mazur L, Ferenc W. Thermal, spectroscopic and structural studies of zinc(II) complex with nicotinamide. J Therm Anal Calorim. 2009;96:255–60.

    Article  Google Scholar 

  33. Modi CK, Patel SH, Patel MN. Transition metal complexes with uninegative bidentate schiff base. Synthetis, thermal, spectroscopic and coordination aspects. J Therm Anal Calorim. 2007;87:441–8.

    Article  CAS  Google Scholar 

  34. Omar MM, Mohamed GG, Hindy AMM. Transition metal complexes of heterocyclic Schiff base. Biological activity, spectroscopic and thermal characterization. J Therm Anal Calorim. 2006;86(2):315–25.

    Article  CAS  Google Scholar 

  35. Mohamed GG, Omar MM, Hindy AMM. Synthesis, characterization and biological activity of some transition metals with Schiff base derived from 2-tiophene carboxaldehyde and aminobenzoic acid. Spectrochim Acta. 2005;A62:1140–50.

    Google Scholar 

  36. Burger K. Coordination chemistry; experimental methods. Budapest: Akadémiai Kiadó; 1973.

    Google Scholar 

  37. Issa YM, El-Ansary AL, Sherif OE, El-Ajiily MM. Separation and spectroscopic characterization of new metal chelates of 8-arylazo-6-formyl-7-hydroxy-5-methoxy-2-methyl chromones. Trans Met Chem. 1997;22:441–6.

    Article  CAS  Google Scholar 

  38. Offiong E, Nfor E, Ayi A. Synthesis, spectral and cytotoxicity studies of palladium(II) and platinum(II) amino acid Schiff base complexes. Trans Met Chem. 2000;25:369–73.

    Article  CAS  Google Scholar 

  39. El-Wahab ZHA, El-Sarrag MR. Derivatives of phosphate Schiff base transition metal complexes: synthesis, studies and biological activity. Spectrochim Acta. 2004;A60:271–7.

    Google Scholar 

  40. Doskocz M, Kubiak K, Frąckowiak A, Gancarz R. NMR and ab initio studies of Mg2+, Ca2+, Zn2+, Cu2+ alizarin complexes. Polyhedron. 2009;28:2201–5.

    Article  CAS  Google Scholar 

  41. Geary W. The use of conductivity measurements in organic solvents for the characterization of coordination compounds. J Coord Chem Rev. 1971;7:81–122.

    Article  CAS  Google Scholar 

  42. Hamman AM, Ibrahim SA, El-Gahami MA, Fouad D. Investigations of Co(II), Ni(II) and Cu(II) (2, 20:60, 200-terpyridine)complexes with sulphur donor ligands. J Therm Anal Calorim. 2003;74:801–10.

    Article  Google Scholar 

  43. Chandra S, Gupta LK, Jain D. Spectroscopic studies on Mn(II), Co(II), Ni(II) and Cu(II) complexes with N-donor tetradentate (N4) macrocyclic ligand derived from ethylcinnamate moiety. Spectrochim Acta. 2004;A60:2411–7.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Agnieszka Dziewulska-Kułaczkowska.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dziewulska-Kułaczkowska, A. Thermal and spectral studies of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes with 3-(anilinomethylene)-2-methoxychroman-4-one. J Therm Anal Calorim 109, 7–15 (2012). https://doi.org/10.1007/s10973-011-1387-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-011-1387-y

Keywords

Navigation