Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2015, Article ID 789063, 12 pages
http://dx.doi.org/10.1155/2015/789063
Research Article

Synthesis, DFT Calculation, and Antimicrobial Studies of Novel Zn(II), Co(II), Cu(II), and Mn(II) Heteroleptic Complexes Containing Benzoylacetone and Dithiocarbamate

1Department of Chemistry, Federal University Ndufu-Alike, Ikwo, PMB 1010, Abakaliki, Ebonyi, Nigeria
2Material Science Innovation and Modelling (MaSIM) Research Focus Area, Faculty of Agriculture, Science and Technology, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho, South Africa
3Department of Chemistry, School of Mathematical and Physical Sciences, Faculty of Agriculture, Science and Technology, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa
4Department of Chemistry, Faculty of Science, Obafemi Awolowo University, Ile-Ife 220005, Nigeria
5Inorganic Unit, Department of Chemistry, University of Ibadan, Ibadan, Nigeria

Received 23 September 2015; Accepted 18 October 2015

Academic Editor: Concepción López

Copyright © 2015 Anthony C. Ekennia et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Shanmugakala, P. Tharmaraj, C. D. Sheela, and N. Chidambaranathan, “Transition metal complexes of s-triazine derivative: new class of anticonvulsant, anti-inflammatory, and neuroprotective agents,” Medicinal Chemistry Research, vol. 23, no. 1, pp. 329–342, 2014. View at Publisher · View at Google Scholar · View at Scopus
  2. M. B. Halli, V. B. Patil, R. B. Sumathi, and K. Mallikarjun, “Synthesis, characterization and biological activity of mixed ligand metal (II) complexes derived from benzofuran-2-carbohydrazide schiff base and malonyldihydrazide,” Der Pharma Chemica, vol. 4, no. 6, pp. 2360–2367, 2012. View at Google Scholar · View at Scopus
  3. R. C. Maurya, P. Sharma, and D. Sutradhar, “Metal thiocyanato complexes: synthesis, magnetic, and spectral studies of some mixed-ligand thiocyanato complexes of nickel(II) involving benzothiazole and benzimidazole derivatives,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 33, no. 3, pp. 387–401, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. Y.-T. Li, C.-W. Yan, C.-Y. Zhu, and H.-S. Guan, “Synthesis and magnetic studies of μ-oxamido-bridged copper(II)–manganese(II) heterobinuclear complexes,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 34, no. 7, pp. 1165–1179, 2004. View at Publisher · View at Google Scholar · View at Scopus
  5. Y. Aydogdu, F. Yakuphanoglu, A. Aydogdu, E. Tas, and A. Cukurovali, “Solid state electrical conductivity properties of copper complexes of novel oxime compounds containing oxolane ring,” Materials Letters, vol. 57, no. 24-25, pp. 3755–3760, 2003. View at Publisher · View at Google Scholar · View at Scopus
  6. S. H. Ramadan, H.-K. Fun, and B. K. Ghosh, “A study on copper(II)-Schiff base-azide coordination complexes: synthesis, X-ray structure and luminescence properties of [Cu(L)(N3)]X (L = Schiff bases; X = ClO4, PF6),” Polyhedron, vol. 24, no. 18, pp. 3091–3097, 2005. View at Publisher · View at Google Scholar
  7. H.-Y. Bie, J.-H. Yu, J.-Q. Xu et al., “Synthesis, structure and non-linear optical property of a copper(II) thiocyanate three-dimensional supramolecular compound,” Journal of Molecular Structure, vol. 660, no. 1–3, pp. 107–112, 2003. View at Publisher · View at Google Scholar · View at Scopus
  8. E. Jóna, M. Kubranová, P. Šimon, and J. Mroziński, “Thermochemical investigation: Ni(II)-3-pyridylcarbinol (ronicol) interactions in solid halogeno and thiocyanato complexes,” Journal of Thermal Analysis, vol. 46, no. 5, pp. 1325–1337, 1996. View at Publisher · View at Google Scholar · View at Scopus
  9. A. S. Mildvan and M. Cohn, “Kinetic and magnetic resonance studies of the pyruvate kinase reaction: II. complexes of enzyme, metal, and substrates,” Journal of Biological Chemistry, vol. 241, no. 5, pp. 1178–1193, 1960. View at Google Scholar · View at Scopus
  10. E. Bouwman, W. L. Driessen, and J. Reedijk, “Model systems for type I copper proteins: structures of copper coordination compounds with thioether and azole-containing ligands,” Coordination Chemistry Reviews, vol. 104, no. 1, pp. 143–172, 1990. View at Publisher · View at Google Scholar · View at Scopus
  11. M. N. Hughes, “Coordination compounds in biology,” in Comprehensive Coordination Chemistry, G. Wilkinson, R. D. Gillard, and J. A. McCleverty, Eds., vol. 6, p. 541, Pergamon Press, Oxford, UK, 1987. View at Google Scholar
  12. N. V. Thakkar and J. R. Thakkar, “Synthesis and characterization of chiral mixed ligand Co(II) complexes of isonitrosopropiophenone and amino acids,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 30, no. 10, pp. 1871–1887, 2000. View at Publisher · View at Google Scholar · View at Scopus
  13. V. S. Shivankar and N. V. Takkar, “Synthesis, characterization and antimicrobial activity of some mixed ligand Co(II) and Ni(II) complexes,” Acta Poloniae Pharmaceutica, vol. 60, no. 1, pp. 45–50, 2003. View at Google Scholar · View at Scopus
  14. R. Kaushal, N. Kumar, A. Chaudhary, S. Arora, and P. Awasthi, “Synthesis, spectral characterization, and antiproliferative studies of mixed ligand titanium complexes of adamantylamine,” Bioinorganic Chemistry and Applications, vol. 2014, Article ID 142828, 12 pages, 2014. View at Publisher · View at Google Scholar · View at Scopus
  15. O. A. Odunola, M. A. Oladipo, J. A. O. Woods, and A. C. Gelebe, “Synthesis and structural studies of ternary copper(II) complexes containing β-diketones with 1,10 phenanthraline and 2,2′ bipyridyl and x-ray structure of [Cu(C6H5COCHCOCH3)(bipy)Cl],” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 33, no. 5, pp. 857–871, 2003. View at Publisher · View at Google Scholar · View at Scopus
  16. H. Khan, A. Badshah, M. Said et al., “Anticancer metallopharmaceutical agents based on mixed-ligand palladium(II) complexes with dithiocarbamates and tertiary organophosphine ligands,” Applied Organometallic Chemistry, vol. 27, no. 7, pp. 387–395, 2013. View at Publisher · View at Google Scholar · View at Scopus
  17. R. C. Mehota, R. Bohva, and D. P. Gaur, Metal β-Diketonates and Allied Derivatives, Academic Press, New York, NY, USA, 1978.
  18. K. C. Joshi and V. N. Pathak, “Metal chelates of fluorinated 1,3-diketones and related compounds,” Coordination Chemistry Reviews, vol. 22, no. 1-2, pp. 37–122, 1977. View at Publisher · View at Google Scholar · View at Scopus
  19. A. A. Osowole, Synthesis, physicochemical and biological properties of cobalt(II), nickel(II) and copper (II) complexes of various substituted β-ketoamines and their adducts [Ph.D. thesis], University of Ibadan, 2002.
  20. J. L. Burdett and M. T. Rogers, “Keto-enol tautomerism in β-dicarbonyls studied by nuclear magnetic resonance spectroscopy. I. Proton chemical shifts and equilibrium constants of pure compounds,” Journal of the American Chemical Society, vol. 86, no. 11, pp. 2105–2109, 1964. View at Publisher · View at Google Scholar · View at Scopus
  21. R. L. Lintvedt and H. F. Holtzclaw Jr., “Proton magnetic resonance spectra and electronic effects in substituted 1,3-diketones,” Journal of the American Chemical Society, vol. 88, no. 12, pp. 2713–2716, 1966. View at Publisher · View at Google Scholar · View at Scopus
  22. S. Kawaguchi, “Variety in the coordination modes of β-dicarbonyl compounds in metal complexes,” Coordination Chemistry Reviews, vol. 70, pp. 51–84, 1986. View at Publisher · View at Google Scholar · View at Scopus
  23. D. W. Thompson and A. L. Allred, “Keto-enol equilibria in 2,4-pentanedione and 3,3-dideuterio-2,4-pentanedione,” Journal of Physical Chemistry, vol. 75, no. 3, pp. 433–435, 1971. View at Publisher · View at Google Scholar · View at Scopus
  24. M. Agrawal, A. Khandelwal, G. Baswal, and S. Bugalia, “Synthesis and spectral studies of mixed ligand complexes of Mn(III) with 2-hydroxypropiophone and substituted salicylaldehyde or β-diketones,” Journal of Applicable Chemistry, vol. 3, no. 3, pp. 1015–1024, 2014. View at Google Scholar
  25. K. C. Kemp, E. Fourie, J. Conradie, and J. C. Swarts, “Ruthenocene-containing β-diketones: synthesis, pKa' values, keto-enol isomerization kinetics, and electrochemical aspects,” Organometallics, vol. 27, pp. 353–362, 2008. View at Google Scholar
  26. K. S. Siddiqi, S. A. A. Nami, Lutfullah, and Y. Chebude, “Template synthesis of symmetrical transition metal dithiocarbamates,” Journal of the Brazilian Chemical Society, vol. 17, no. 1, pp. 107–112, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. R. Say, E. Birlik, Z. Erdemgil, A. Denizli, and A. Ersöz, “Removal of mercury species with dithiocarbamate-anchored polymer/organosmectite composites,” Journal of Hazardous Materials, vol. 150, no. 3, pp. 560–564, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Ünlü and M. Ersoz, “Removal of heavy metal ions by using dithiocarbamated-sporopollenin,” Separation and Purification Technology, vol. 52, no. 3, pp. 461–469, 2007. View at Publisher · View at Google Scholar · View at Scopus
  29. F. Fu, H. Zeng, Q. Cai, R. Qiu, J. Yu, and Y. Xiong, “Effective removal of coordinated copper from wastewater using a new dithiocarbamate-type supramolecular heavy metal precipitant,” Chemosphere, vol. 69, no. 11, pp. 1783–1789, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. Y. Yoshikawa, Y. Adachi, and H. Sakurai, “A new type of orally active anti-diabetic Zn(II)-dithiocarbamate complex,” Life Sciences, vol. 80, no. 8, pp. 759–766, 2007. View at Publisher · View at Google Scholar · View at Scopus
  31. S. Ozkirimli, T. I. Apak, M. Kiraz, and Y. Yegenoglu, “Synthesis of new triazolyl-N,N-dialkyldithiocarbamates as antifungal agents,” Archives of Pharmacal Research, vol. 28, no. 11, pp. 1213–1218, 2005. View at Publisher · View at Google Scholar · View at Scopus
  32. F. Shaheen, A. Badshah, M. Gielen, C. Gieck, M. Jamil, and D. de Vos, “Synthesis, characterization, in vitro cytotoxicity and anti-inflammatory activity of palladium(II) complexes with tertiary phosphines and heterocyclic thiolates: crystal structure of [PdC28H19N8PS2],” Journal of Organometallic Chemistry, vol. 693, no. 6, pp. 1117–1126, 2008. View at Publisher · View at Google Scholar · View at Scopus
  33. V. Alverdi, L. Giovagnini, C. Marzano et al., “Characterization studies and cytotoxicity assays of Pt(II) and Pd(II) dithiocarbamate complexes by means of FT-IR, NMR spectroscopy and mass spectrometry,” Journal of Inorganic Biochemistry, vol. 98, no. 6, pp. 1117–1128, 2004. View at Publisher · View at Google Scholar · View at Scopus
  34. R. Singh and N. K. Kaushik, “Spectral and thermal studies with anti-fungal aspects of some organotin(IV) complexes with nitrogen and sulphur donor ligands derived from 2-phenylethylamine,” Spectrochimica Acta—Part A: Molecular and Biomolecular Spectroscopy, vol. 71, no. 2, pp. 669–675, 2008. View at Publisher · View at Google Scholar · View at Scopus
  35. S. M. Mamba, A. K. Mishra, B. B. Mamba, P. B. Njobeh, M. F. Dutton, and E. Fosso-Kankeu, “Spectral, thermal and in vitro antimicrobial studies of cyclohexylamine-N-dithiocarbamate transition metal complexes,” Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy, vol. 77, no. 3, pp. 579–587, 2010. View at Publisher · View at Google Scholar · View at Scopus
  36. A. Earnshew, Introduction to Magnetochemistry, Academic Press, London, UK, 1980.
  37. A. C. Ekennia, D. C. Onwudiwe, and A. A. Osowole, “Spectral, thermal stability and antibacterial studies of copper, nickel and cobalt complexes of N-methyl-N-phenyl dithiocarbamate,” Journal of Sulfur Chemistry, vol. 36, no. 1, pp. 96–104, 2015. View at Publisher · View at Google Scholar · View at Scopus
  38. D. C. Onwudiwe and P. A. Ajibade, “Synthesis and crystal structure of Bis(N-alkyl-N-phenyl dithiocarbamato)mercury(II),” Journal of Chemical Crystallography, vol. 41, no. 7, pp. 980–985, 2011. View at Publisher · View at Google Scholar · View at Scopus
  39. A. D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Physical Review A, vol. 38, no. 6, pp. 3098–3100, 1988. View at Publisher · View at Google Scholar · View at Scopus
  40. C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, no. 2, pp. 785–789, 1988. View at Publisher · View at Google Scholar · View at Scopus
  41. I. Georgieva and N. Trendafilova, “Bonding analyses, formation energies, and vibrational properties of M-R2dtc complexes (M = Ag(I), Ni(II), Cu(II), or Zn(II)),” The Journal of Physical Chemistry A, vol. 111, no. 50, pp. 13075–13087, 2007. View at Publisher · View at Google Scholar
  42. L. Chen, T. Liu, and C. Ma, “Metal complexation and biodegradation of EDTA and S,S-EDDS: a density functional theory study,” Journal of Physical Chemistry A, vol. 114, no. 1, pp. 443–454, 2010. View at Publisher · View at Google Scholar · View at Scopus
  43. Y. Niu, S. Feng, Y. Ding, R. Qu, D. Wang, and J. Han, “Theoretical investigation on sulfur-containing chelating resin-divalent metal complexes,” International Journal of Quantum Chemistry, vol. 110, no. 10, pp. 1982–1993, 2010. View at Publisher · View at Google Scholar · View at Scopus
  44. S. I. Gorelsky, L. Basumallick, J. Vura-Weis et al., “Spectroscopic and DFT investigation of [M{HB(3,5-iPr2pz)3} (SC6F5)] (M = Mn, Fe, Co, Ni, Cu, and Zn) model complexes: periodic trends in metal-thiolate bonding,” Inorganic Chemistry, vol. 44, no. 14, pp. 4947–4960, 2005. View at Publisher · View at Google Scholar
  45. M. Belcastro, T. Marino, N. Russo, and M. Toscano, “Interaction of cysteine with Cu2+ and Group IIb (Zn2+, Cd2+, Hg2+) metal cations: a theoretical study,” Journal of Mass Spectrometry, vol. 40, no. 3, pp. 300–306, 2005. View at Publisher · View at Google Scholar · View at Scopus
  46. T. Marino, M. Toscano, N. Russo, and A. Grand, “Structural and electronic characterization of the complexes obtained by the interaction between bare and hydrated first-row transition-metal ions (Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+) and glycine,” Journal of Physical Chemistry B, vol. 110, no. 48, pp. 24666–24673, 2006. View at Publisher · View at Google Scholar · View at Scopus
  47. R. Terreux, M. Domard, C. Viton, and A. Domard, “Interactions study between the copper II ion and constitutive elements of chitosan structure by DFT calculation,” Biomacromolecules, vol. 7, no. 1, pp. 31–37, 2006. View at Publisher · View at Google Scholar · View at Scopus
  48. J. C. Amicangelo, “Theoretical characterization of a tridentate photochromic Pt(II) complex using density functional theory methods,” Journal of Chemical Theory and Computation, vol. 3, no. 6, pp. 2198–2209, 2007. View at Publisher · View at Google Scholar · View at Scopus
  49. F. Tarazona-Vasquez and P. B. Balbuena, “Dendrimer-tetrachloroplatinate precursor interactions. 1. Hydration of Pt(II) species and PAMAM outer pockets,” Journal of Physical Chemistry A, vol. 111, no. 5, pp. 932–944, 2007. View at Publisher · View at Google Scholar · View at Scopus
  50. F. Tarazona-Vasquez and P. B. Balbuena, “Dendrimer-tetrachloroplatinate precursor interactions. 2. Noncovalent binding in PAMAM outer pockets,” Journal of Physical Chemistry A, vol. 111, no. 5, pp. 945–953, 2007. View at Publisher · View at Google Scholar · View at Scopus
  51. T. H. Dunning Jr. and P. J. Hay, Modern Theoretical Chemistry, edited by H. F. Schaefer III, Plenum, New York, NY, USA, 1976.
  52. P. J. Hay and W. R. Wadt, “Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg,” The Journal of Chemical Physics, vol. 82, no. 1, pp. 270–283, 1985. View at Publisher · View at Google Scholar · View at Scopus
  53. W. R. Wadt and P. J. Hay, “Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi,” The Journal of Chemical Physics, vol. 82, no. 1, pp. 284–298, 1985. View at Publisher · View at Google Scholar · View at Scopus
  54. P. J. Hay and W. R. Wadt, “Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitale,” The Journal of Chemical Physics, vol. 82, no. 1, pp. 299–310, 1985. View at Publisher · View at Google Scholar · View at Scopus
  55. J. Sabolović, C. S. Tautermann, T. Loerting, and K. R. Liedl, “Modeling anhydrous and aqua copper(II) amino acid complexes:  a new molecular mechanics force field parametrization based on quantum chemical studies and experimental crystal data,” Inorganic Chemistry, vol. 42, no. 7, pp. 2268–2279, 2003. View at Publisher · View at Google Scholar · View at Scopus
  56. M. Y. Combariza and R. W. Vachet, “Effect of coordination geometry on the gas-phase reactivity of four-coordinate divalent metal ion complexes,” Journal of Physical Chemistry A, vol. 108, no. 10, pp. 1757–1763, 2004. View at Publisher · View at Google Scholar · View at Scopus
  57. M. A. Carvajal, J. J. Novoa, and S. Alvarez, “hoice of coordination number in d10 complexes of group 11 metals,” Journal of the American Chemical Society, vol. 126, no. 5, pp. 1465–1477, 2004. View at Publisher · View at Google Scholar · View at Scopus
  58. B. D. Alexander and T. J. Dines, “Ab initio calculations of the structures and vibrational spectra of ethene complexes,” Journal of Physical Chemistry A, vol. 108, no. 1, pp. 146–156, 2004. View at Publisher · View at Google Scholar · View at Scopus
  59. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 09, Revision D.01, Gaussian, Wallingford, Conn, USA, 2009.
  60. A. A. Nejo, G. A. Kolawole, M. C. Dumbele, and A. R. Opoku, “Spectral, magnetic, biological, and thermal studies of metal (II) complexes of some unsymmetrical Schiff bases,” Journal of Coordination Chemistry, vol. 63, no. 24, pp. 4367–4379, 2010. View at Publisher · View at Google Scholar · View at Scopus
  61. M. Tunçel and S. Serin, “Synthesis and characterization of copper(II), nickel(II) and cobalt(II) complexes with azo-linked schiff base ligands,” Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, vol. 35, no. 3, pp. 203–212, 2005. View at Publisher · View at Google Scholar
  62. S. M. E. Khalil, H. S. Seleem, B. A. El-Shetary, and M. Shebl, “Mono- and bi-nuclear metal complexes of schiff-base hydrazone (ONN) derived from o-hydroxyacetophenone and 2-amino-4-hydrazino-6-methyl pyrimidine,” Journal of Coordination Chemistry, vol. 55, no. 8, pp. 883–899, 2002. View at Publisher · View at Google Scholar · View at Scopus
  63. A. Earnshaw, The Introduction to Magnetochemistry, Academic Press, New York, NY, USA, 1980.
  64. F. A. Cotton, G. Wilkinson, C. A. Murillo, and M. Bochmann, Advanced Inorganic Chemistry, John Wiley & Sons, New York, NY, USA, 1999.
  65. N. S. R. Koteswara Rao and M. G. R. Reddy, “Studies on the synthesis, characterisation and antimicrobial activity of new Co(II), Ni(II) and Zn(II) complexes of Schiff base derived from ninhydrin and glycine,” Biology of Metals, vol. 3, no. 1, pp. 19–23, 1990. View at Publisher · View at Google Scholar · View at Scopus
  66. S. M. Abu-el Wafa and R. M. Issa, “The preparation of a series of Mn(II) complexes of the type [Mn(SB)SO2],” Bulletin de la Société Chimique de France, vol. 5, pp. 595–598, 1989. View at Google Scholar
  67. A. A. Osowole, A. A. Oni, K. Onyegbula, and A. T. Hassan, “Synthesis, spectral, magnetic and in-vitro anticancer properties of some metal (II) complexes of 3-[2,4-dihydro-1H-inden-4-ylimino) methyl] napthalene-2-ol,” International Research Journal of Pure and Applied Chemistry, vol. 2, no. 3, pp. 211–220, 2012. View at Publisher · View at Google Scholar
  68. W. J. Geary, “The use of conductivity measurements in organic solvents for the characterisation of coordination compounds,” Coordination Chemistry Reviews, vol. 7, no. 1, pp. 81–122, 1971. View at Publisher · View at Google Scholar · View at Scopus
  69. IUPAC, Compendium of Chemical Terminology, Gold Book, 2nd edition, 1997.
  70. T. C. Higgs, K. Spartalian, C. J. O'Connor, B. F. Matzanke, and C. J. Carrano, “Synthesis and characterization of a series of edge-sharing octahedral-tetrahedral octahedral linear trinuclear complexes [M3(L1O)4]2+, where M = Mn2+, Co2+, Ni2+, Cu2+, and Zn2+ and LiOH is the ‘Heteroscorpionate’ ligand (2-hydroxyphenyl)bis(pyrazolyl)methane,” Inorganic Chemistry, vol. 37, pp. 2263–2272, 1998. View at Google Scholar
  71. D. Sun, R. Cao, Y. Liang, Q. Shi, W. Su, and M. Hong, “Hydrothermal syntheses, structures and properties of terephthalate-bridged polymeric complexes with zig-zag chain and channel structures,” Journal of the Chemical Society, Dalton Transactions, vol. 16, pp. 2335–2340, 2001. View at Google Scholar · View at Scopus
  72. E. Ruiz, J. Cirera, and S. Alvarez, “Spin density distribution in transition metal complexes,” Coordination Chemistry Reviews, vol. 249, no. 23, pp. 2649–2660, 2005. View at Publisher · View at Google Scholar · View at Scopus
  73. J. Cano, E. Ruiz, S. Alvarez, and M. Verdaguer, “Spin density distribution in transition metal complexes: some thoughts and hints,” Comments on Inorganic Chemistry, vol. 20, no. 1, pp. 27–56, 1998. View at Publisher · View at Google Scholar · View at Scopus
  74. H. Irving and R. J. P. Williams, “The stability of transition-metal complexes,” Journal of the Chemical Society, vol. 8, pp. 3192–3210, 1953. View at Publisher · View at Google Scholar
  75. G. W. Luther, D. T. Rickard, S. Theberge, and A. Olroyd, “Determination of metal (Bi)sulfide stability constants of Mn2+, Fe2+, Co2+, Ni2+, Cu2+, and Zn2+ by voltammetric methods,” Environmental Science and Technology, vol. 30, no. 2, pp. 671–679, 1996. View at Publisher · View at Google Scholar · View at Scopus
  76. A. A. Osowole, I. Ott, and O. M. Ogunlana, “Synthesis, spectroscopic, anticancer, and antimicrobial properties of some Metal(II) complexes of (substituted) nitrophenol schiff base,” International Journal of Inorganic Chemistry, vol. 2012, Article ID 206417, 6 pages, 2012. View at Publisher · View at Google Scholar