Synthesis and Characterization of new Schiff base Ligand type [N4O4] from 3-(Ethoxymethylene)pentane-2.4-dione and its Niп Complex

Eman I. Alsalihi

Abstract


The Schiff base reaction plays an important role in the condensation reaction between 3-(ethoxymethylene) pentane- 2.4-dione and 3,3’-diaminobenzidine in the presence of calculated amounts of KOH as a catalyst. This reaction has been carried out in the ethanol under reflux and overnight stirring condition. All syntheses were carried out under an atmosphere of hydrogen forming a new ligand [3,3’,3’’,3’’’-(1E,1’E,1’’E,1’’’E)-(biphenyl-3,3’,4,4’-tetrayltetrakis (azan-1-yl-1-ylidene)) tetrakis (methan-1- yl-1-ylidene) tetrakis (4-methoxybut-3-en-2-one)] type [N4O4]. The ligand and its Niп complex of the general formula [Ni2(L)] have been characterized by spectroscopic methods (Fourier transform infrared and ultraviolet-visible), elemental analysis (C.H.N), metal content, magnetic susceptibility measurement, thin-layer chromatography, mass spectrometry, X-ray powder diffraction powder diffraction, 1H-nuclear magnetic resonance, molar conductance, and biological activity. The ligand and its Ni complex were exposed to two types of bacteria (Staphylococcus aureus and Bacillus subtilis), using the agar disc diffusion method, and the ligand and its Niп complex exhibited significant activities against these two types of bacteria. Our study revealed the formation of a new ligand type [N4O4] and four-coordinate tetrahedral structure around Niп metal ion with the ratio of 1:2 (ligand:metal) stable compounds which can be used in many fields, such as medicine and industry.

Keywords


Index Terms—3-(Ethoxymethylene)pentane-2.4-dione, Nickel(II) acetate hydrate-99+%, Four-coordinate tetrahedral complex, Structural study, Schiff bases.

Full Text:

PDF

References


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, M.A., Mirza, A.H., and Butcher R.J., 2001. Synthesis and characterization of copper(II) complexes of the methylpyruvate Schiff base of S-methyldithiocarbazate (Hmpsme) and the X-crystal structures of Hmpsme and [Cu(mpsme)Cl]. Polyhedron, 20(9-10), pp.1037-1043.

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.

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

Anne-Louise, H., Jack, T., Howard, S., Abdelwahid, M., Veronique, D., Georges, L., and Ian, B., 2005. Rate coefficients for the reactions of OH radicals with the keto/enol tautomers of 2,4-pentanedione and 3-methyl-2,4-pentanedione, allyl alcohol and methyl vinyl ketone using the enols and methyl nitrite as

photolytic sources of OH. Journal of Photochemistry and Photobiology A: Chemistry, 176(1-3), pp.183-190.

Anto, P.L., Anto, R.J., Varghese, H.T., Panicker, C.Y., Philipe, D. and Brolof, A.G., 2009. FT-IR, FT-Raman and SERS spectra of anilinium sulphate. Journal of Raman Spectroscopy, 40, pp.1810-1815.

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, p.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.

Baran, E.J., Viera, I., and Torre, M.H., 2007. Vibrational spectra of the Cu(II) complexes of L-asparagine and L-glutamine. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 66A, p.114.

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

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.

Dhanaraj, C.J., and Nair, M.S., 2014. Synthesis and characterization of cobalt (II) and zinc (II) complexes of poly(3-nitrobenzyli dene-1-naphthylamine-cosuccinic anhydride). Journal of Saudi Chemical Society, 18(5), pp.479-485.

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.

Devi, G.K.D., and Mohamed, M.I.F., 2012. Afacile synthesis of phenyl phenacyl ethers. Der Chemica Sinica, 3(1), pp.71-75.

Griffith, D.M., Szocs, B., Keogh, T., Suponitsky, K.Y., Farkas, E., Buglyó, P., and Marmion, C.J., 2011. Suberoylanilide hydroxamic acid, a potent histone deacetylase inhibitor; Its X-ray crystal structure and solid state and solution studies of its Zn(II), Ni(II), Cu(II) and Fe(III) complexes. Journal of Inorganic Biochemistry, 105, pp.763-769.

Hans, S., and Dieter, M., 2005. Benzidine and benzidine derivatives. In: Ullmann’s Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim.

Qian, H.F., and Huang, W., 2010. Biphenyl-3,3’,4,4’-tetraamine. Acta Crystallographica Section E, E66(5), p.1060.

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(Supplement 1), pp.S457-S466.

Kettle, S.F.A., 1975. Coordination Compounds. Thomas Nelson and Sons, London, p.165.

Khalaj, A.D., and Das, D., 2014. Synthesis and characterization of NiO nanoparticles via solid-state thermal decomposition of Nickal(II) Schiff base complexes. International Nano Letters, 4, p.117.

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-hydroxy- 3-methoxybenzylidene)

benzoylhydrazone and HL2=pyridine-4-carboxylic (isonicotinic) acid. Dalton Transactions, 40, pp.1286-1294.

Petra, D., Tatjano, Z., and Boriset, P., 2005. Mixed-valence Cu(II)/Cu(I) complex of quinolone ciprofloxacin isolated by a hydrothermal reaction in the presence of l-histidine: Comparison of biological activities of various copper-ciprofloxacin compounds. Journal of Inorganic Biochemistry, 2, pp.432-442.

Roeges, N.P.G., 1994. A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures. Wiley, New York.

Shayma, A.S., Khaledi, H., Cheah, S.C., and Ali, H.M., 2016. New Mn(II), Ni(II), Cd(II), Pb(II) complexes with 2-ethylbenzimidazole and other ligands. Synthesis, spectroscopic characterization, crystal structure, magnetic susceptibility and biological activity studies. Arabian Journal of Chemistry, 9(Supplement 2), pp.S1943-S1950.

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.305-310.

Tauber, S.C., and Nau, R., 2008. Immunomodulatory properties of antibiotics. Current Molecular Pharmacology, 1, p.68.

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.

Varghese, H.T., Panicker, C.Y., Anto, P.L., and Philip, D., 2006. Potential‐dependent SERS profile of orthanilic acid on silver electrode. Journal of Raman Spectroscopy, 37, pp.1265-1271.

Yang, W., Yuanjun, S., Lei, Z., Nahla, R., Bo, J., and Yudong, H., 2016. An investigation of the high performance of a novel type of benzobisoxazole fiber based on 3,3-diaminobenzidine. Polymers, 8, p.420.

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(3), p.92.




DOI: http://dx.doi.org/10.14500/aro.10460
View Counter: Abstract | 187 | and PDF | 145 |

Article Metrics

Metrics Loading ...

Metrics powered by PLOS ALM

Refbacks

  • There are currently no refbacks.


Copyright (c) 2019 Eman I. Alsalihi

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

  
 


ARO Journal is an OAJ supported by Koya University, it has no article submission/processing charges (APCs).
© 2013-2019, Koya University is a public University accredited by the Ministry of Higher Education and Scientific Research, KRG - F.R. Iraq.