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Synthesis, characterization of new homo and heteronuclear Schiff base copper(II) complexes

Year 2018, Volume: 5 Issue: 2, 785 - 802, 01.01.2018
https://doi.org/10.18596/jotcsa.324878

Abstract

This
article describes the synthesis of
isonitrosomethyl-p-tolyl
ketone [HL]
as
the starting material and then we prepared the schiff base ligand from the reactions
of the amine compounds with
o-phenylenediamine [H2L1]. A new series of mono-, homo and heterodinuclear copper(II)/nickel(II)
complexes have been synthesized using an oxime ligand. The complexes were
characterized by IR, elemental analysis, magnetic moment measurements, molar
conductivity, mass spectra and TGA studies. The free ligand were also described
13C and 1H-NMR spectra.
For complexes using
stoichiometric and spectroscopic data of the metal complexes showed that metal:ligand
ratio of mononuclear copper(II) complex was found to be 1:1 while this ratio
was 2:1 in homo- and heterodinuclear copper(II) complex and 3:2 in the
trinuclear copper (II) complex and metal ions are coordinated to the imine and
oxime nitrogen atoms. 

References

  • 1. Kahn O. Dinuclear Complexes with Predictable Magnetic Properties. Angew. Chem., Int. Ed. Engl. 1985 October; 24: 834-850.
  • 2. Smith A. G, Tasker P. A and White, D. J. The structures of phenolic oximes and their complexes. The Coord. Chem. Rev. 2003; 241: 61-85.
  • 3. Cheng, M. Y, De B, Almstead N. G, Pikul S, Dowty M. E, Dietsch C. R, Dunaway C. M, Gu F, Hsieh L. C, Janusz M. J, Taiwo Y. O, Natchus M. G, Hudlicky T, and Mandel M. Design, synthesis, and biological evaluation of matrix metalloproteinase inhibitors derived from a modified proline scaffold. J. Med. Chem. 1999; 42: 5426-5436.
  • 4. Kitajima N. and Moro-oka Y. Copper-Dioxygen Complexes. Inorganic and Bioinorganic Perspectives. Chem. Rev. 1994; 94: 737-757.
  • 5. Reddy K. H, Reddy P.S. Nuclease activity of mixed ligand complexes of copper(II) with heteroaromatic derivatives and picoline. Transition Met. Chem. 2000; 25: 505-510.
  • 6. Kane S. A, Hecht S.M. Polynucleotide recognition and degradation by bleomycin. Prog Nucleic Acid Res Mol Biol. 1994; 49: 313–352.
  • 7. Borah S, Melvin M.S, Lindquist N, Manderville R.A . Copper-mediated nuclease activity of a tambjamine alkaloid. J Am Chem Soc. 1998; 120: 4557-4562.
  • 8. Asad S. F, Singh S, Ahmad A, Hadi S.M. Bilirubin- Cu(II) complex degrades DNA. Biochim. Biophys. Acta. 1999; 1428: 201-208.
  • 9. Dulger S, Saglam N, Belduz A, Guner S, Karabocek S. Dna Cleavage By Homo- And Heterotetranuclear Cu(II) And Mn(II) Complexes With Tetrathioether-Tetrathiol Moiety. Biometals. 2000; 13: 261-265.
  • 10. Athar F, Arjmand F, Tabassum S. New asymmetric N2S2 macrocycles, their metal chelates and the photokinetics of DNA-complex interaction. Transition Met. Chem. 2001; 26: 426-429.
  • 11. Saglam N, Colak A, Serbest K, Dulger S, Guner S, Karabocek S, Belduz AO. Oxidative cleavage of DNA by homo- and heteronuclear Cu(II)-Mn(II) complexes of an oxime-type ligand. Biometals. 2002; 15: 357-365.
  • 12. Garcia-Raso A, Fiol JJ, Adrover B, Moreno V, Mata I, Espinosa E, Molins E. Synthesis, structure and nuclease properties of several ternary copper(II) peptide complexes with 1,10-phenanthroline. J.Inorg. Biochem. 2003; 95: 77-86.
  • 13. Gonzalez-Alvarez M, Alzuet G, Borras J, Macias B, del Olmo M, Liu-Gonzalez M, Sanz F. Nuclease activity of [Cu(sulfathiazolato)(2)(benzimidazole)(2)](2)MeOH. Synthesis, properties and crystal structure. J. Inorg. Biochem. 2002; 89: 29-35.
  • 14. Karplus P.A, Pearson M.A. 70 years of crystalline urease: What have we learned?. Acc. Chem. Res. 1997; 30: 330-337.
  • 15. Zhu H.L, Tong Y.X, Chen X.M, Ren C.X. Synthesis, crystal structures and physical properties of two terephthalate-bridged copper(II) and nickel(II) complexes. Transition Met. Chem. 2001; 26: 528-531.
  • 16. Lashanizadegan M, Boghaei D.M. Metal complexes of non-symmetric tetradentate Schiff bases derived from N-(2-hydroxyacetophenone)-1-amino-2-phenyleneimine. Synth. React. Met.-Org. Chem. 2000; 30: 89-98.
  • 17. Lashanizadegan M, Boghaei D.M. Template synthesis and X-ray structure determination of unsymmetrical tetradentate Schiff base complexes of nickel(II) and copper(II). Synth. React. Met.-Org. Chem. 2001; 31: 1519-1529.
  • 18. Boghaei D.M, Mohebi S. Novel unsymmetrical tetradentate Schiff base complexes of cobalt (II) and palladium (II) with N2O2 donor sets. J. Chem. Res. (S) 2001; 224-226.
  • 19. Hoyos O.L, Bermejo M.R, Fondo M, Garcia-Daide A, Gonzalez A.M, Maneiro M.B, Pedrido R. Mn(III) complexes with asymmetrical N2O3 Schiff bases. The unusual crystal structure of [Mn(phenglydisal-3-Br,5-Cl)(dmso)] (H(3)phenglydisal=3-aza-N-{2-[1-aza-2-(2-hydroxyphenyl)-vinyl]phenyl}-4-(2-hydroxyphenyl)but-3-enamide), a mononuclear single-stranded helical manganese(III) complex. J. Chem. Soc., Dalton Trans. 2000; 3122-3127.
  • 20. Atkins R, Brewer G, Kokot E, Mockler G.M, Sinn E. Copper(II) and Nickel(II) complexes of unsymmetrical tetradentate schiff-base ligands. Inorg.Chem. 1985;24: 127-134.
  • 21. Karapinar E, Özcan E, Synthesis of N '-[4 '-benzo(15-crown-5)]-4-tolylaminoglyoxime and N '-[4 '-benzo(15-crown-5)]-4-chlorophenylaminoglyoxime and their complexes with copper (II), nickel (II) and cobalt (II). Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2003; 47: 59-63.
  • 22. Pekacar A.I, Özcan E. The Synthesis of 5 new bis(amino-p-chlorophenyl-glyoximes) and their polymeric complexes with Ni(II), Co(II) and Cu(II). Journal of Macromolecular science-pure and applied chemistry 1994; 31: 651-661.
  • 23. Sevindir H.C, Mirzaoğlu R. Synthesis and complex-formation of 4 new unsymmetrical vic-dioximes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 1992; 22: 851-861.
  • 24. Dede B, Özmen İ, Karipcin F. Synthesis, characterization, catalase functions and DNA cleavage studies of new homo and heteronuclear Schiff base copper(II) complexes. Polyhedron 2009; 28: 3967-3974.
  • 25. Dede B, Karipcin F, Cengiz M, Novel homo- and hetero-nuclear copper(II) complexes of tetradentate Schiff bases: Synthesis, characterization, solvent-extraction and catalase-like activity studies. J. of Hazardous Materials 2009; 163: 1148–1156.
  • 26. Dede B, Karipcin F, Cengiz M. Synthesis, characterization and extraction studies of N,N ''-bis[1-biphenyl-2-hydroxyimino-2-(4-acetylanilino)-1-ethylidene]- diamines and their homo-and heteronuclear copper(II) complexes. J. Chem. Sci. 2009; 121: 163–171.
  • 27. Karabocek S, Karabocek N, Armutcu A. Synthesis and structural studies of 2-(hydroxyimino)-1-methylpropylideneamino-phenyliminobutan-2-one oxime, ligand and its complexes with Cu-(II) and Ni-(II). Transition Metal Chemistry 2006; 31: 459–464,
  • 28. Prushan M.J, Addison A.W, Butcher R.J, Thompson L.K. Copper(II) complexes of tetradentate thioether-oxime ligands. Inorg. Chim. Acta 2005; 358: 3449–3456.
  • 29. Ucan S.Y, Mercimek B. Synthesis and characterization of tetradentate N2O2 Schiff base ligands and their transition metal complexes. Synth. and React. Inorg. Met-Org. and Nano-metal Chem. 2005; 35: 197–201.
  • 30. Chitrapriya N, Mahalingam V, Zeller M, Lee H, Natarajan K. Synthesis, characterization, DNA binding and cleavage studies of Ru(II) complexes containing oxime ligands. J. Mol Struc. 2010; 984: 30–38.
  • 31. Serbest K, Karabocek S, Degirmencioglu I, Guner S, Kormali F. Mono-, di- and trinuclear copper(II) dioxime complexes; 3-{2-[2-(2-hydroxyimino-1-methylpropylideneamino)ethylamino]ethylimino}butan-2-one oxime. Trans. Met. Chem. 2001; 26: 375–379.
  • 32. Prushan M.J, Addison A.W, Butcher R.J. Thompson L.K, Copper(II) complexes of tetradentate thioether-oxime ligands. Inorg. Chim. Acta 2005; 358: 3449–3456.
  • 33. Karipcin F, Ucan H.I, Karatas I. Binuclear and mononuclear cobalt(II), nickel(II) and copper(II) complexes of 4,4 '-bis(alkylaminoisonitrosoacetyl)diphenyl-methane derivatives. Trans. Met. Chem. 2002; 27: 813–817.
  • 34. Ferraro J.R. Low Frequency Vibrations of Inorganic and Coordination Compounds. Plenum Press, 1971, New York,
  • 35. David M.A. Metal–Ligand and Related Vibrations. Adward Arnold Ltd. 1967, London
  • 36. Serbest K, Colak A, Guner S, Karabocek S, Kormalı F. Copper(II)-manganese(II) complexes of 3,3 '-(1,3-propanediyldiimine)bis-(3-methyl-2-butanone)dioxime with superoxide dismutase-like activity. Transition Met. Chem. 2001; 26: 625-629
  • 37. Bonomo R.P, Conte E, Marchelli R, Santoro A.M, Tabbi G. O-2(-) Scavenger properties of copper(II) complexes with diamino-diamide-type ligands. J. Inorg. Biochem. 1994; 53: 127-138
  • 38. Karabocek N, Armutcu A, Karabocek S. Synthesis and structural studies of (2E,3E)-3-[(6-{[(1E,2E)-2-(hydroxyimino)-1-methylpropylidene]amino}pyridin-2-yl)imino]butan-2-one oxime, ligand and its mono-, di- and trinuclear copper(II) complexes. Inorg. Chim. Acta, 2006; 31: 938-942.
  • 39. Karipcin F, Baskale-Akdogan G. Synthesis and characterization of novel oxime-imine ligands and their heteronuclear ruthenium(III) complexes. Russian Journal of Coordination Chem. 2009; 35: 588–596.
  • 40. Geary W.J. The use of conductivity measurements in organic solvents fort he characterisation of coordination compounds. Coord. Chem. Rev. 1971; 7: 81-122.
  • 41. Kulkarrni N.D, Bhattcharya P.K. Study of binuclear copper(II) complexes involving bridging schiff bases-I. Transition Met. Chem. 1989; 14: 303-305
  • 42. Ruiz R, Lloret F, Julve M, Faus J. A study of Exchange interaction through phenolato, oximato and oxamidato bridges in (MnCuII)-Cu-II dimers- Crystal-Structure of [Cu(Salen)Mn(hfa)(2)]. Inorg. Chim. Acta. 1993; 213: 261-268.
  • 43. Luneau D, Oshio H, Okawa H, Koikawa M, Kida S. Synthesis, structure, and magnetism of binuclear Cu(II)Cu(II), Cu(II)Ni(II) and Ni(II)Ni(II) complexes doubly bridged by oxymate groups. Bull. Chem. Soc. of Jpn. 1990; 63: 2212-2217.
  • 44. Karabocek S, Karabocek N, Mono- and dinuclear copper(II) complexes of a Schiff base ligand, 4',5'-bis(salicylideneimino)benzo-15-crown-5. Polyhedron. 1997; 16: 1771-1774.
  • 45. Karabocek S, Bayraktar U, Karabocek N, Sahin Z.S, Işık S, Muhsir S. Synthesis of (2E,3E,10E,12E)-3,11-dimethyl-5,9-dioxa-4,10-diazatrideca-3,10-diene-2,12-dione dioxime and its Cu(II), Ni(II), and Co(II) complexes. Journal of Coordination Chem. 2012; 65: 1118-1129.
Year 2018, Volume: 5 Issue: 2, 785 - 802, 01.01.2018
https://doi.org/10.18596/jotcsa.324878

Abstract

References

  • 1. Kahn O. Dinuclear Complexes with Predictable Magnetic Properties. Angew. Chem., Int. Ed. Engl. 1985 October; 24: 834-850.
  • 2. Smith A. G, Tasker P. A and White, D. J. The structures of phenolic oximes and their complexes. The Coord. Chem. Rev. 2003; 241: 61-85.
  • 3. Cheng, M. Y, De B, Almstead N. G, Pikul S, Dowty M. E, Dietsch C. R, Dunaway C. M, Gu F, Hsieh L. C, Janusz M. J, Taiwo Y. O, Natchus M. G, Hudlicky T, and Mandel M. Design, synthesis, and biological evaluation of matrix metalloproteinase inhibitors derived from a modified proline scaffold. J. Med. Chem. 1999; 42: 5426-5436.
  • 4. Kitajima N. and Moro-oka Y. Copper-Dioxygen Complexes. Inorganic and Bioinorganic Perspectives. Chem. Rev. 1994; 94: 737-757.
  • 5. Reddy K. H, Reddy P.S. Nuclease activity of mixed ligand complexes of copper(II) with heteroaromatic derivatives and picoline. Transition Met. Chem. 2000; 25: 505-510.
  • 6. Kane S. A, Hecht S.M. Polynucleotide recognition and degradation by bleomycin. Prog Nucleic Acid Res Mol Biol. 1994; 49: 313–352.
  • 7. Borah S, Melvin M.S, Lindquist N, Manderville R.A . Copper-mediated nuclease activity of a tambjamine alkaloid. J Am Chem Soc. 1998; 120: 4557-4562.
  • 8. Asad S. F, Singh S, Ahmad A, Hadi S.M. Bilirubin- Cu(II) complex degrades DNA. Biochim. Biophys. Acta. 1999; 1428: 201-208.
  • 9. Dulger S, Saglam N, Belduz A, Guner S, Karabocek S. Dna Cleavage By Homo- And Heterotetranuclear Cu(II) And Mn(II) Complexes With Tetrathioether-Tetrathiol Moiety. Biometals. 2000; 13: 261-265.
  • 10. Athar F, Arjmand F, Tabassum S. New asymmetric N2S2 macrocycles, their metal chelates and the photokinetics of DNA-complex interaction. Transition Met. Chem. 2001; 26: 426-429.
  • 11. Saglam N, Colak A, Serbest K, Dulger S, Guner S, Karabocek S, Belduz AO. Oxidative cleavage of DNA by homo- and heteronuclear Cu(II)-Mn(II) complexes of an oxime-type ligand. Biometals. 2002; 15: 357-365.
  • 12. Garcia-Raso A, Fiol JJ, Adrover B, Moreno V, Mata I, Espinosa E, Molins E. Synthesis, structure and nuclease properties of several ternary copper(II) peptide complexes with 1,10-phenanthroline. J.Inorg. Biochem. 2003; 95: 77-86.
  • 13. Gonzalez-Alvarez M, Alzuet G, Borras J, Macias B, del Olmo M, Liu-Gonzalez M, Sanz F. Nuclease activity of [Cu(sulfathiazolato)(2)(benzimidazole)(2)](2)MeOH. Synthesis, properties and crystal structure. J. Inorg. Biochem. 2002; 89: 29-35.
  • 14. Karplus P.A, Pearson M.A. 70 years of crystalline urease: What have we learned?. Acc. Chem. Res. 1997; 30: 330-337.
  • 15. Zhu H.L, Tong Y.X, Chen X.M, Ren C.X. Synthesis, crystal structures and physical properties of two terephthalate-bridged copper(II) and nickel(II) complexes. Transition Met. Chem. 2001; 26: 528-531.
  • 16. Lashanizadegan M, Boghaei D.M. Metal complexes of non-symmetric tetradentate Schiff bases derived from N-(2-hydroxyacetophenone)-1-amino-2-phenyleneimine. Synth. React. Met.-Org. Chem. 2000; 30: 89-98.
  • 17. Lashanizadegan M, Boghaei D.M. Template synthesis and X-ray structure determination of unsymmetrical tetradentate Schiff base complexes of nickel(II) and copper(II). Synth. React. Met.-Org. Chem. 2001; 31: 1519-1529.
  • 18. Boghaei D.M, Mohebi S. Novel unsymmetrical tetradentate Schiff base complexes of cobalt (II) and palladium (II) with N2O2 donor sets. J. Chem. Res. (S) 2001; 224-226.
  • 19. Hoyos O.L, Bermejo M.R, Fondo M, Garcia-Daide A, Gonzalez A.M, Maneiro M.B, Pedrido R. Mn(III) complexes with asymmetrical N2O3 Schiff bases. The unusual crystal structure of [Mn(phenglydisal-3-Br,5-Cl)(dmso)] (H(3)phenglydisal=3-aza-N-{2-[1-aza-2-(2-hydroxyphenyl)-vinyl]phenyl}-4-(2-hydroxyphenyl)but-3-enamide), a mononuclear single-stranded helical manganese(III) complex. J. Chem. Soc., Dalton Trans. 2000; 3122-3127.
  • 20. Atkins R, Brewer G, Kokot E, Mockler G.M, Sinn E. Copper(II) and Nickel(II) complexes of unsymmetrical tetradentate schiff-base ligands. Inorg.Chem. 1985;24: 127-134.
  • 21. Karapinar E, Özcan E, Synthesis of N '-[4 '-benzo(15-crown-5)]-4-tolylaminoglyoxime and N '-[4 '-benzo(15-crown-5)]-4-chlorophenylaminoglyoxime and their complexes with copper (II), nickel (II) and cobalt (II). Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2003; 47: 59-63.
  • 22. Pekacar A.I, Özcan E. The Synthesis of 5 new bis(amino-p-chlorophenyl-glyoximes) and their polymeric complexes with Ni(II), Co(II) and Cu(II). Journal of Macromolecular science-pure and applied chemistry 1994; 31: 651-661.
  • 23. Sevindir H.C, Mirzaoğlu R. Synthesis and complex-formation of 4 new unsymmetrical vic-dioximes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 1992; 22: 851-861.
  • 24. Dede B, Özmen İ, Karipcin F. Synthesis, characterization, catalase functions and DNA cleavage studies of new homo and heteronuclear Schiff base copper(II) complexes. Polyhedron 2009; 28: 3967-3974.
  • 25. Dede B, Karipcin F, Cengiz M, Novel homo- and hetero-nuclear copper(II) complexes of tetradentate Schiff bases: Synthesis, characterization, solvent-extraction and catalase-like activity studies. J. of Hazardous Materials 2009; 163: 1148–1156.
  • 26. Dede B, Karipcin F, Cengiz M. Synthesis, characterization and extraction studies of N,N ''-bis[1-biphenyl-2-hydroxyimino-2-(4-acetylanilino)-1-ethylidene]- diamines and their homo-and heteronuclear copper(II) complexes. J. Chem. Sci. 2009; 121: 163–171.
  • 27. Karabocek S, Karabocek N, Armutcu A. Synthesis and structural studies of 2-(hydroxyimino)-1-methylpropylideneamino-phenyliminobutan-2-one oxime, ligand and its complexes with Cu-(II) and Ni-(II). Transition Metal Chemistry 2006; 31: 459–464,
  • 28. Prushan M.J, Addison A.W, Butcher R.J, Thompson L.K. Copper(II) complexes of tetradentate thioether-oxime ligands. Inorg. Chim. Acta 2005; 358: 3449–3456.
  • 29. Ucan S.Y, Mercimek B. Synthesis and characterization of tetradentate N2O2 Schiff base ligands and their transition metal complexes. Synth. and React. Inorg. Met-Org. and Nano-metal Chem. 2005; 35: 197–201.
  • 30. Chitrapriya N, Mahalingam V, Zeller M, Lee H, Natarajan K. Synthesis, characterization, DNA binding and cleavage studies of Ru(II) complexes containing oxime ligands. J. Mol Struc. 2010; 984: 30–38.
  • 31. Serbest K, Karabocek S, Degirmencioglu I, Guner S, Kormali F. Mono-, di- and trinuclear copper(II) dioxime complexes; 3-{2-[2-(2-hydroxyimino-1-methylpropylideneamino)ethylamino]ethylimino}butan-2-one oxime. Trans. Met. Chem. 2001; 26: 375–379.
  • 32. Prushan M.J, Addison A.W, Butcher R.J. Thompson L.K, Copper(II) complexes of tetradentate thioether-oxime ligands. Inorg. Chim. Acta 2005; 358: 3449–3456.
  • 33. Karipcin F, Ucan H.I, Karatas I. Binuclear and mononuclear cobalt(II), nickel(II) and copper(II) complexes of 4,4 '-bis(alkylaminoisonitrosoacetyl)diphenyl-methane derivatives. Trans. Met. Chem. 2002; 27: 813–817.
  • 34. Ferraro J.R. Low Frequency Vibrations of Inorganic and Coordination Compounds. Plenum Press, 1971, New York,
  • 35. David M.A. Metal–Ligand and Related Vibrations. Adward Arnold Ltd. 1967, London
  • 36. Serbest K, Colak A, Guner S, Karabocek S, Kormalı F. Copper(II)-manganese(II) complexes of 3,3 '-(1,3-propanediyldiimine)bis-(3-methyl-2-butanone)dioxime with superoxide dismutase-like activity. Transition Met. Chem. 2001; 26: 625-629
  • 37. Bonomo R.P, Conte E, Marchelli R, Santoro A.M, Tabbi G. O-2(-) Scavenger properties of copper(II) complexes with diamino-diamide-type ligands. J. Inorg. Biochem. 1994; 53: 127-138
  • 38. Karabocek N, Armutcu A, Karabocek S. Synthesis and structural studies of (2E,3E)-3-[(6-{[(1E,2E)-2-(hydroxyimino)-1-methylpropylidene]amino}pyridin-2-yl)imino]butan-2-one oxime, ligand and its mono-, di- and trinuclear copper(II) complexes. Inorg. Chim. Acta, 2006; 31: 938-942.
  • 39. Karipcin F, Baskale-Akdogan G. Synthesis and characterization of novel oxime-imine ligands and their heteronuclear ruthenium(III) complexes. Russian Journal of Coordination Chem. 2009; 35: 588–596.
  • 40. Geary W.J. The use of conductivity measurements in organic solvents fort he characterisation of coordination compounds. Coord. Chem. Rev. 1971; 7: 81-122.
  • 41. Kulkarrni N.D, Bhattcharya P.K. Study of binuclear copper(II) complexes involving bridging schiff bases-I. Transition Met. Chem. 1989; 14: 303-305
  • 42. Ruiz R, Lloret F, Julve M, Faus J. A study of Exchange interaction through phenolato, oximato and oxamidato bridges in (MnCuII)-Cu-II dimers- Crystal-Structure of [Cu(Salen)Mn(hfa)(2)]. Inorg. Chim. Acta. 1993; 213: 261-268.
  • 43. Luneau D, Oshio H, Okawa H, Koikawa M, Kida S. Synthesis, structure, and magnetism of binuclear Cu(II)Cu(II), Cu(II)Ni(II) and Ni(II)Ni(II) complexes doubly bridged by oxymate groups. Bull. Chem. Soc. of Jpn. 1990; 63: 2212-2217.
  • 44. Karabocek S, Karabocek N, Mono- and dinuclear copper(II) complexes of a Schiff base ligand, 4',5'-bis(salicylideneimino)benzo-15-crown-5. Polyhedron. 1997; 16: 1771-1774.
  • 45. Karabocek S, Bayraktar U, Karabocek N, Sahin Z.S, Işık S, Muhsir S. Synthesis of (2E,3E,10E,12E)-3,11-dimethyl-5,9-dioxa-4,10-diazatrideca-3,10-diene-2,12-dione dioxime and its Cu(II), Ni(II), and Co(II) complexes. Journal of Coordination Chem. 2012; 65: 1118-1129.
There are 45 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Tufan Topal

Emin Karapınar

Publication Date January 1, 2018
Submission Date June 30, 2017
Acceptance Date May 6, 2018
Published in Issue Year 2018 Volume: 5 Issue: 2

Cite

Vancouver Topal T, Karapınar E. Synthesis, characterization of new homo and heteronuclear Schiff base copper(II) complexes. JOTCSA. 2018;5(2):785-802.

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