Synthesis and Antibacterial Activity of Isatin Schiff Base Derivative with 3-Aminoacetophenone and its Ni(II), Co(II) Transition Metals Complexes

Keywords: 3-aminoacetophenone, Bidentate ligand and (N) donor atoms, Isatin, Schiff base


The (E)-3-(3-acetylphenylimino) indolin-2-one (Bidentate) ligand type [HL], has been prepared from Isatin and 3-aminoacetophenone in the presence of KOH. In general, the ligand contains oxygen (O) and nitrogen (N) donor atoms. The reaction of Isatin and 3-aminoacetophenon was carried out in ethanol by condensation reaction at 80°C with reflux for 4 h, to form [HL] ligand type. This ligand has been used to prepare NiII and CoII complexes in the ratio of 1:1 metal-ligand. All compounds have been characterized by spectroscopic methods (Fourier transform infrared and ultravioletvisible), C.H.N, thin-layer chromatography, mass spectrum, X-ray diffraction, magnetic moment, conductivity measurements and milting point, the synthesized ligand and its metal complexes have been tested for their antibacterial activity against Staphylococcus aureus and Bacillus subtilis using agar disc diffusion method. The ligand and its complexes showed significant activities against S. aureus and B. subtilis. Our study revealed the formation of four coordinate square planar complexes around NiII and CoII metal ions.


Download data is not yet available.

Author Biographies

Eman I. Alsalihi, Department of Chemistry, Faculty of Science and Health, Koya university, Kurdistan Region

Dr. Eman Ibraheem Alsalihi is a Lecturer, joined the Department of Chemistry, Faculty of Science and HEalth at Koya University in 2009. She has a B.Sc. degree in Chemistry, M.Sc. degree in Inorganic Chemistry and Ph.D. degree in Inorganic Chemistry. She is a membership of the ACS (American Chemical Society) since 2015 . Dr. Eman has (10) published Journal articles. 

Aeed S. Al-Fahdawi, Department of Chemistry, College of Education for Women, University of Anbar, Ramadi, Anbar
Dr. Aeed Salih Mohammed is an Assistant Professor. He joined the Department of Chemistry, College of Education for Women at the the University of Anbar in 2001. He  has a B.Sc. degree in Chemistry, M.Sc. degree in Inorganic Chemistry and Ph.D. degree in Inorganic Chemistry, he has (10) published Journal Articles.


Abu-Dief Ahmed, A.M. and Mohamed, I.M.A., 2015. A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-Suef University Journal of Basic and Applied Sciences, 4, pp.119-133.

Ali, H., Al-Azawi, S., Silverschtien, R.M., Bassler, G.C. and Morril, T.C., 1981. Spectrophotometers Indentification of Organic Compounds. John Wiley and Sons, New York.

Al-Jeboori, M.J., Al-Tawel, H.H. and Mahmood, R., 2010. New metal complexes of N2S2 tetradentate ligands: Synthesis and spectral studies. Inorganica Chimica Acta, 363, pp.1301-1305.

AL-Shihri, A.S., 2004. Spectrochimica acte. Part A, 60, pp.1189-1192.

Anacona, J.R. 2006. Synthesis and antibacterial activity of some metal complexes of β-. Lactams antibiotics. Journal of Coordination Chemistry, 54, pp.355-365.

Anuradha, K. and Rajarel, R., 2011. Synthesis, spectral characterization and biological activity of new symmetrical macrocyclic binuclear Schiff base complexes. Internatiol Journal of Pharmacy and Technology, 2, pp.2217.

Asadi M., Sepehrpour, H. and Mohammadi, K.H., 2011. “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. Journal of the Serbian Chemical Society, 76, pp.63-74.

Available from: literature/2016_styrene_product_safety_bulletin.pdf.

Braish, T. and Gadamasetti, K., 2007. Process Chemistry in the Pharmaceutical Industry, Vol. 2. CRC Press, Boca Raton, pp.142-145.

Chamayou, A.C., Lüdeke, S., Brecht, V., Freedman, T.B., Nafie, L.A. and Janiak, C., 2011. Chirality and diastereoselection of Δ/∇-configured tetrahedral zinc complexes through enantiopure Schiff base complexes: Combined vibrational circular dichroism, density functional theory, 1 H NMR, and X-ray structural studies. Inorganic Chemistry,50, pp.11363-11374.

Colchoubian, H., Waltz, W.L. and Quail, J.W., 1999. Synthesis and characterization of Schiff base folic acid based ligand and its complexes. Canadian Journal of Chemistry, pp.37-77.

Da Silva Cleiton, M., da Silva Daniel, L., Modolo, L.V., Alves, R.B., de Resende, M.A., Martins, C.V.B. and Ângelode, F., 2011. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2, pp.1-8.

Dokken, K.M., Parsons, J.G., McClure, J. and Gardea-Torresdey, J.L., 2009. Synthesis and structural analysis of copper(II) cysteine complexes. Inorganica Chimica Acta, 362, pp.395-401.

Guillemet-Fritsch, S., Lebey, T., Boulos, M. and Durand, B. 2006. Dielectric properties of CaCu3Ti4O12 based multiphased ceramics. Journal of the European Ceramic Society, 26, pp.1245-1257.

Halli, M.B., Patil, V.B., Sumathi, R.B. and Mallikarjun, K., 2012. Synthesis, characterization and biological activity of mixed ligand metal (II) complexes derived from benzofuran-2-carbohydrazide schiff base and malonyldihydrazide. Der Pharma Chemica, 4, pp.2360-2323.

Ivanov, I. and Nikolova, S., 2008. Synthesis of New β-enaminones of Isoquinolines with 5, 5-Dimethyl-cyclohexanedione. Molbank, Plovdiv. pp.565.

Jakels, S.C., Ciavola, J., Carter, R.C., Cheek, P.L. and Pascarlli, T.D., 1983. Inorganic Chemistry, 22, pp.3956.

Jarrahpour, A.A. and Khalili, D., 2005. Synthesis of some new bis-Schiff Bases of Isatin and 5-fluoroisatin in a water suspension medium. Molecules, 11, pp.59-63.

Kai, Y., Gu, Z., Ji, R. and Lou, L.S., 2009. Heterogeneous chiral Mn(111) salen catalysts for the epoxidation of unfunvtionalized olefins immobilized on mesoporous materials with different pore sizes. Tetrahedron, 65, pp.305-311.

Kavitha, N. and Lakshm, P.V.A., 2017. Synthesis, characterization and thermogravimetric analysis of Co(II), Ni(II), Cu(II) and Zn(II) complexes supported by ONNO tetradentdate Schiff base ligand derived from hydrazine benzoxazine. Journal of Saudi Chemical Society, 21 Suppl 1, pp.S457-S466.

Kindeel, A.S., Dawood, I.J. and Aziz, M.R., 2013. Synthesis and characterization of some mixed ligand complexes containing (8-hydroxyquinoline) and (2-picoline) with some metal ions. Baghdad Science Journal, 10, pp.396.

Lever, A.B.P., 1984. Inorganic Electronic Spectroscopy. 2nd ed., Elsevier, New York.

Monfared, H.H., Vahedpour, M., Yeganeh, M.M., Ghorbanloo, M., Mayer, P. and Janiak, C. 2011. Concentration dependent tautomerism in green [Cu(HL1)(L2)] and brown [Cu(L1)(HL2)] with H2L1=(E)-N′-(2-hydroxy3-methoxybenzylidene) benzoylhydrazone and HL2=pyridine-4-carboxylic (isonicotinic) acid. Dalton Transactions, 40, pp.1286-1294.

Nakamoto, K., 1997. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Parts A and B. 5th ed. John Wiley Sons, New York. Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names. 2013. Blue Book. The Royal Society of Chemistry, Cambridge. pp.723.

Refat, M.S., and Struct, J.M., 2007. Complexes of uranyl (II), vanadyl (II) and zirconyl (II) with orotic acid “vitamin B13”: Synthesis, spectroscopic, thermal studies and antibacterial activity. Article in Journal of Molecular Structure, 842, pp.24.

Rostkowska, N.M.J., Lapinski, L., Bertner, M., Kulikowski, T., Les, A. and Adamowicz, L., 1993. Spectrochim. Acta A. 49, pp.551.

Shaker, A.M., Nassr, L.A.E. and Adam, M.M.S.S., 2013. Synthesis, characterization and spectrophotometric studies of seven novel antibacterial hydrophilic iron (II) Schiff base amino acid complexes. Journal of the Korean Chemical Society, 5, pp.560.

Sultana, N. and Arayne, M.S., 2007. In vitro activity of cefadroxil, cephalexin, cefatrizine and cefpirome in presence of essential and trace elements. Pakistan Journal of Pharmaceutical Sciences, 20, pp.305-10.

Uppadin, L.H., Weeks, J.M. and Beer, P.D., 2001. Metal-directed self-assembly of terphenyl based dithiocarbamate ligands. Journal of the Chemical Society Dalton Transactions, 22, pp.3367-3372.

Yadav, J.S., Reddy, B.V.S., Reddy, C.S. and Krishna, A., 2007. Indium(III) chloride/2-iodoxybenzoic acid: A novel reagent system for the conversion of indoles to isatins. Synthesis. 5, pp.693-696.

Zheng, Z., Junwei, X., Sisi, Y., Yangli, C., Yan, W., Zhuo, C. and Chunlin, N., 2017. Two organic cation salts containing tetra (isothiocyanate)cobaltate(II): Synthesis, crystal structures, spectroscopic, optical and magnetic properties. Crystals, 7, pp.92.

How to Cite
Alsalihi, E. I. and Al-Fahdawi, A. S. (2018) “Synthesis and Antibacterial Activity of Isatin Schiff Base Derivative with 3-Aminoacetophenone and its Ni(II), Co(II) Transition Metals Complexes”, ARO-THE SCIENTIFIC JOURNAL OF KOYA UNIVERSITY, 6(1), pp. 38-45. doi: 10.14500/aro.10245.