Abstract
New metal(II)/(III) complexes with novel Schiff base, resulted from the condensation of propane-1,3-diamine with bisaldehyde, as tetradentate ligand have been synthesized and characterized using elemental analyses, spectra (IR, 1H NMR and ESR), molar conductance, magnetic moment, and thermal studies. The IR data suggest the coordination mode for the Schiff base ligand which behaves as a tetradentate with the metal ions. Based on the elemental analysis, magnetic studies, electronic, and ESR data, octahedral geometry was proposed for the complexes. The ESR spectra of the Cu(II) complex in powdered form showed an axial symmetry with 2B1g as ground state and hyperfine structure. The thermal stability and degradation of the Schiff base ligand and its metal complexes were studied by TG. The molar conductance in DMF solution indicates that all complexes are electrolytes. The free Schiff base ligand and its metal complexes were tested for their in vitro antimicrobial activity against gram-positive and gram-negative organisms. The results showed that the synthesized complexes exhibited higher antimicrobial activity than their free Schiff base ligand. Of all the studied complexes, the Cu(II) and Co(II) complexes exhibited high antimicrobial activity at low micromolar inhibitory concentrations compared to the other complexes, amikacin standard, and the free Schiff base ligand.
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Abd El-Halim HF, Nour El-Dien FA, Mohamed GG, Mohamed NA. Chelating behavior, thermal studies and biocidal efficiency of tioconazole and its complexes with some transition metal ions. J Therm Anal Calorim. 2013;111:173–81.
Manav N, Gandhi N, Kaushik NK. Some tribenzyl tin(IV) complexes with thiohydrazides and thiodiamines. synthesis, characterization and thermal studies. J Therm Anal Calorim. 2000;61:127–34.
Mishra AK, Mishra SB, Manav N, Kaushik NK. Thermal and spectral studies of palladium(II) complexes. J Therm Anal Calorim. 2007;90(2):509–15.
Abd El Wahed MG, Nour EM, Teleb S, Fahim S. Thermodynamic and thermal investigation of Co(II), Ni(II) AND Cu(II) complexes with adenine. J Therm Anal Calorim. 2004;76:343.
Zayed MA, Hawash MF, Fahmey MA, El-Gizouli AMA. Investigation of ibuprofen drug using mass spectrometry, thermal analyses and semi-empirical molecular orbital calculation. J Therm Anal Calorim. 2012;108:315–22.
Abd El-Halim HF, Nour El-Dien FA, Mohamed GG, Mohamed NA. Synthesis, pectroscopic. thermal characterization, and antimicrobial activity of miconazole drug and its metal complexes. J Therm Anal Calorim. 2012;109:883–92.
Zayed MA, Mohamed GG, Fahmey MA. Thermal and mass spectral characterization of novel azo dyes of p-acetoamidophenol in comparison with Hammett substituent effects and molecular orbital calculations. J Therm Anal Calorim. 2012;107:763–76.
Refat MS, Mohamed GG, Farias RF, Powell AK, El-Garib MS, El-Korashy SA, Hussien MA. Spectroscopic, thermal and kinetic studies of coordination compounds of Zn(II), Cd(II) and Hg(II) with norfloxacin. J Therm Anal Calorim. 2010;102:225–32.
Choppin GR, Bunzli JCG. Lanthanide probes in life. Medical and environmetal sciences. Amsterdam: Elsevier; 1989.
Chaudhary A, Bansal N, Gajraj A, Singh RV. Antifertility, antibacterial, antifungal and percent disease incidence aspects of macrocyclic complexes of manganese(II). J Inorg Biochem. 2003;96:393–400.
Soliman MH, Mohamed GG, Mohamed EA. Metal complexes of fenoterol drug. J Therm Anal Calorim. 2010;99:639–47.
Melson GA. Coordination chemistry of macrocyclic compounds. New York: Plenum Press; 1979.
Sahani MK, Yadava U, Pandey OP, Sengupta SK. Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione. Spectrochim Acta Part A. 2014;125:189–94.
Tverdova NV, Pelevina ED, Giricheva NI, Girichev GV, Kuzmina NP, Kotova OV. Molecular structures of 3d metal complexes with various Schiff bases studied by gas-phase electron diffraction and quantum-chemical calculations. J Mol Struct. 2012;1012:151–61.
Anitha C, Sheela CD, Tharmaraj P, Sumathi S. Spectroscopic studies and biological evaluation of some transitionmetal complexes of azo Schiff-base ligand derived from (1-phenyl-2,3-dimethyl-4-aminopyrazol-5-one) and 5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde. Spectrochim Acta A. 2012;96:493–500.
Raman N, Sobha S, Thamaraichelvan A. Anovel bioactive tyramine derived Schiff base and its transition metal complexes as selective DNA binding agents. Spectrochim Acta A. 2011;78:888–98.
Alaghaz AMA, Bayoumi HA, Ammar YA, Aldhlmani SA. Synthesis, characterization, and antipathogenic studies of some transition metal complexes with N, O-chelating Schiff’s base ligand incorporating azo and sulfonamide Moieties. J Mol Struct. 2013;13:383–99.
Halli MB, Sumathi RB, Kinni M. Synthesis, spectroscopic characterization and biological evaluation studies of Schiff’s base derived from naphthofuran-2-carbohydrazide with 8-formyl-7-hydroxy-4-methyl coumarin and its metal complexes. Spectrochim Acta A. 2012;99:46–56.
Garnovskii AD, VasilChenko IS. Rational design of metal coordination compounds with azomethine ligands. Russ Chem Rev. 2002;71:943–96.
Mohamed GG. Synthesis, characterization and biological activity of bis(phenylimine) Schiff base ligands and their metal complexes. Spectrochim Acta Part A. 2006;64:188–95.
Hassan WMI, Zayed EM, Elkholy AK, Moustafa H, Mohamed GG. Spectroscopic and density functional theory investigation of novel Schiff base complexes. Spectrochim. Acta A. 2013;103:378–87.
Khalil MMH, Ismail EH, Mohamed GG, Zayed EM, Kamel AB. Synthesis and characterization of bisaldehyde ligand with some transition metals and its application in spectrophotometric determination of Fe(III) in natural water samples using recovery test. Egypt J Pure Appl Sci. 2011; 029-037.
Khalil MMH, Ismail EH, Mohamed GG, Zayed EM, Badr A. Synthesis and characterization of a novel Schiff base metal complexes and their application in determination of iron in different types of natural water. Open J Inorg Chem. 2012;2:13–21.
Zayed EM, Sokker HH, Albishri HM, Farag AM. Ecol. Eng., Potential use of novel modified fishbone for anchoring hazardous metal ions from their solutions. Ecol Eng. 2013;61(61):390–3.
Dean JA, editor. Lange’s handbook of chemistry. 14th ed. New York: McGraw-Hill; 1992 Table 8.35.
Ilhan S, Temel H, Yilmaz I, Sekerci M. Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes. J Organomet Chem. 2007;692:3855–65.
Zayed EM, Ismail EH, Mohamed CG, Khalil MMH, Kamel MMH. Synthesis, spectroscopic and structural characterization, and antimicrobial studies of metal complexes of a new hexadentate Schiff base ligand. Spectrophotometric determination of Fe(III) in water samples using a recovery test. Monatsh Chem. 2014;145:755–65.
Cotton FA, Wilkinson G, Murillo CA, Bochmann M. Advanced in Schiff base chemistry. 6th ed. New York: Wiley; 1999.
Hodnett EM, Mooney PD. Antitumor activities of some Schiff bases. Eur J Med Chem. 1970;13:586–90.
Mahmoud WH, Mohamed CG, El-Dessouky MMI. Coordination modes of bidentate lornoxicam drug with some transition metal ions. Synthesis, characterization and in vitro antimicrobial and antibreastic cancer activity studies. Spectrochim Acta A. 2014;122:598–608.
Mahmoud WH, Mohamed GG. El-Dessouky. Synthesis, characterization and in vitro biological activity of mixed transition metal complexes of lornoxicam with 1,10-phenanthroline. Int J Electrochem Sci. 2014;9:1415–38.
Richthofen CG, Stammler A, Bogge H, Glaser T. Synthesis and characterization of trinuclear Ni(II) and Cu(II) triplesalophen complexes: evaluation of ligand folding and heteroradialene formation and their impact on the magnetic properties. Eur J Inorg Chem. 2012;36:5934–52.
Karthikeyan MS, Parsad DJ, Poojary B, Bhat KS, Holla BS, Kumari NS. Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety. Bioorg Med Chem. 2006;14:7482–9.
Mladenova R, Ignatova M, Manolova N, Petrova T, Rashkov I. Preparation, characterization and biological activity of Schiff base compounds derived from 8-hydroxyquinoline-2-carboxaldehyde and Jeffamines ED. Eur Polym J. 2002;38:989–99.
Panneerselvam P, Nair RR, Vijayalakshmi G, Subramanian EH, Sridhar SK. Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents. Eur J Med Chem. 2005;40:225–9.
Singh K, Barwa MS, Tyagi P. Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate Schiff bases derived by heterocyclic ketone. Eur J Med Chem. 2006;41:147–53.
Sari N, Arslan S, Logoglu E, Sakiyan I. Antibacterial activities of some amino acid Schiff bases. Gazi Univ J Sci. 2003;16:283–8.
Tarushi A, Christofis P, Psomas G. Synthesis, characterization and interaction with DNA of mononuclear metal complexes with oxolinic acid. Polyhedron. 2007;26:3963–72.
Efthimiadou EK, Katsaros N, Karaliota A, Psomas G. Synthesis, characterization, antibacterial activity, and interaction with DNA of the vanadyl-enrofloxacin complex. Bioorg Med Chem Lett. 2007;17:1238–42.
Dendrinou-Samara C, Psomas G, Raptopoulou CP, Kessissoglou DK. Copper(II) complexes with phenoxyalkanoic acids and nitrogen donor heterocyclic ligands: structure and bioactivity. J Inorg Biochem. 2001;83:7–16.
Dharmaraj N, Viswanathamurthi P, Natarajan K. Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity. Transit Met Chem. 2001;26:105–9.
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Zayed, E.M., Mohamed, G.G. & Hindy, A.M.M. Transition metal complexes of novel Schiff base. J Therm Anal Calorim 120, 893–903 (2015). https://doi.org/10.1007/s10973-014-4061-3
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DOI: https://doi.org/10.1007/s10973-014-4061-3