Document Type : Research Paper

Authors

1 Department of Chemistry, College of Education for Pure Science (Ibn Al-Haitham), University of Baghdad, Baghdad, Iraq

2 Department of Chemistry, College of Education for Pure Science (Ibn Al-Haitham), University of Baghdad, Adhamiyah, Baghdad, Iraq

Abstract

: A new azo-Schiff base ligand derived from an p-anisidine moiety and its monomeric metal complexes were prepared and characterised. The titled ligand, (1-((E)-((4-methoxy phenyl) imino) methyl)-3-((E)-(4-nitrophenyl)diazenyl) naphthalen-2-ol) (HL), was obtained through the reaction of p-anisidine and ((E)-2-hydroxy-3-((4-nitrophenyl)diazenyl)-1-naphthaldehyde) in a 1:1 mole ratio. The interaction of HL with selected metal ions, including CrIII, MnII, CoII, NiII and CuII in a mole ratio of 1:1 (L:M), resulted in the formation of monomeric coordination compounds. Several analytical and spectroscopic techniques were used to analyse the prepared compounds.These techniques include elemental microanalysis, 1H and 13C NMR, FT-IR, electronic and mass spectra, magnetic susceptibility and conductance. Characterisation data confirmed the formation of sixand four-coordinate coordination compounds. The thermal stability (TGA) of HL and Co-complex are examined. The antimicrobial activity of the prepared compounds toward several microorganisms (bacteria and fungi species) was explored.The collected data shows that the antimicrobial activity of the ligand was improved after forming a complex.

Keywords

Main Subjects

  • [1].Giovanni, D. A. R., Giuseppe, B., and Andrea, F.,2014. Quantitative Determination of 26 Aromatic Amines Derived from Banned Azo Dyes in Textiles Through the Use of LC, Tandem MS, and Identification of Some Structural Isomers.

    [2]. Hakimi, M., Kukovec, B. M., & Minoura, M. (2012). 2D sd Mixed-Metal Coordination Polymer Containing Potassium, Chromium (III) and Dipicolinate Ions: Preparation and Crystal Structure. Journal of chemical crystallography42(3), 290-294.‏

    [3].Hasan A. H, Enaam I.Y and  Ahmed K. H.,CoII, NiII and CdII complexes derived from mixed Azo-linked schiff-base ligands: Formation, characterisation, thermal analysis and biological study., (2020) Journal of Plant Archives.,V.20 (1). pp. 2405-2411.

    [4].E. I. Yousif.,Synthesis and Characterization of Novel Tetradentate ligand Type N4 and its Complexes With CoII,NiII,andPdII., IBN AL- HAITHAM J. FO R PURE & APPL. SC I., 22, 4, 1-13.

    [5]. Enaam I. Yousif and Hasan A. Hasan.,Formation of New Macrocyclic Complexes with bis(Dithiocarbamate) Ligand; Preparation, Structural Characterisation and Bacterial Activity., 2017.,IBN AL- HAITHAM J. FO R PURE & APPL. SC I 29 (3), 146-166.

    [6].Ahmed Ibrahim Ahmed, Enaam I.Y.,(New Metal Complexes with Azo ligand; Synthesis, Spectral Characterisation and Biological Evaluation).,

    • M H S Vol. 16, No. 07, 2022

    [7].Enaam.I.Yousif and Hasan A. Hasan.,New Bis(dithiocarbamate) Ligand for Complex Formation; Synthesis, Spectral Analysis and Bacterial Activity.,2017., IBN AL- HAITHAM J. FO R PURE & APPL. SC I.,30,1, 73-87.

    [8]. Uddin, M. N., Siddique, Z. A., Mase, N., Uzzaman, M., &Shumi, W. (2019). Oxotitanium (IV) complexes of some bis‐unsymmetric Schiff bases: Synthesis, structural elucidation and biomedical applications. Applied Organometallic Chemistry33(6), e4876.‏

    [9]. Ghosh, P., Dey, S. K., Ara, M. H., Karim, K., & Islam, A. B. M. (2019). A review on synthesis and versatile applications of some selected Schiff bases with their transition metal complexes. Egyptian Journal of Chemistry62(Special Issue (Part 2) Innovation in Chemistry), 523-547.‏

    [10]. Abdel-Shakour, M., El-Said, W. A., Abdellah, I. M., Su, R., & El-Shafei, A. (2019). Low-cost Schiff bases chromophores as efficient co-sensitizers for MH-13 in dye-sensitized solar cells. Journal of Materials Science: Materials in Electronics30(5), 5081-5091.‏

    [11]. Karrouchi, K., Brandán, S. A., Hassan, M., Bougrin, K., Radi, S., Ferbinteanu, M., & Garcia, Y. (2021). Synthesis, X-ray, spectroscopy, molecular docking and DFT calculations of (E)-N'-(2, 4-dichlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide. Journal of Molecular Structure1228, 129714.‏

    [12]. Nourifard, F., &Payehghadr, M. (2016). Conductometric studies and application of new Schiff base ligand as carbon paste electrode modifier for mercury and cadmium determination. International Journal of Environmental Analytical Chemistry96(6), 552-567.‏

    [13]. Singh, L. P., &Bhatnagar, J. M. (2004). Copper (II) selective electrochemical sensor based on Schiff Base complexes. Talanta64(2), 313-319.‏

    [14]. Al Zoubi, W., Al‐Hamdani, A. A. S., &Kaseem, M. (2016). Synthesis and antioxidant activities of Schiff bases and their complexes: a review. Applied Organometallic Chemistry30(10), 810-817.‏

    [15]. Karman, M., &Romanowski, G. (2020). Cis-dioxidomolybdenum (VI) complexes with chiral tetradentate Schiff bases: Synthesis, spectroscopic characterization and catalytic activity in sulfoxidation and epoxidation. InorganicaChimicaActa511, 119832.‏

    [16]. Shetty, P. (2020). Schiff bases: An overview of their corrosion inhibition activity in acid media against mild steel. Chemical Engineering Communications207(7), 985-1029.‏

    [17]. Abdel-Rahman, L. H., Abu-Dief, A. M., Adam, M. S. S., &Hamdan, S. K. (2016). Some new nano-sized mononuclear Cu (II) Schiff base complexes: design, characterization, molecular modeling and catalytic potentials in benzyl alcohol oxidation. Catalysis Letters146(8), 1373-1396.‏

    [18]. Manimaran, A., Prabhakaran, R., Deepa, T., Natarajan, K., &Jayabalakrishnan, C. (2008). Synthesis, spectral characterization, electrochemistry and catalytic activities of Cu (II) complexes of bifunctional tridentate Schiff bases containing O N O donors. Applied Organometallic Chemistry22(7), 353-358.‏          

    [19].Kocaokutgen, H., and Erdem, E., 2004. Synthesis and Spectral Characterization of Metal Complexes of 1‐(2‐Hydroxy‐4‐methylphenylazo)‐2‐naphthol. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry34(10), pp.1843-1853.‏

    [20]. Law, K. Y., Tarnawskyj, I. W., and Lubberts, P. T., 1993. Azo pigments and their intermediates: Effect of substitution on the diazotization and coupling reactions of o-hydroxyanilines. Dyes and pigments23(4), pp.243-254.‏

    [21]. Baron EJ, Finegold SM (1990) Diagnostic Microbiology. 8th Ed. Mosby Company. London., 53-62

    22].SilverschtienR.M., Bassler and Morril, “Spectrophotometers Indentification of Organic    Compound”, Translated by Ali Hussain and Suphi Al-Azawi. 1981.

    [23].Mohan, C., Kumar, V., Kumari, N., Kumari, S., Yadav, J., Gandass, T., and Yadav, S., 2020. Synthesis, Characterization and Antibacterial Activity of Semicarbazide Based Schiff Bases and their Pb (II), Zr (IV) and U (VI) Complexes. J. Adv. Chem2, pp.187-196.‏

    [24].Swati, G., Romila, K., Sharma, I. K., and Verma, P. S., 2011. Synthesis, characterization and antimicrobial screening of some azo compounds. Int. J. Appl. Biol. Pharm. Tech2(2), pp.332-38.‏

    [25].Hussein, S. A., and Yousif, E. I., 2021. New Mannich Base (2R)-4-methyl-2-((S)(phenylamino)(p-tolyl) methyl) cyclohexan-1-one; Synthesis and Spectral Characterisation. In Journal of Physics: Conference Series (Vol. 1999, No. 1), pp.012019.

    [26].Alasmi, A., and Merza, J., 2017. Synthesis and characterization of novel dialdehydes based on SN2 reaction of aromatic aldehyde. Inorg. Chem. Ind. J12(1), pp.111.‏

    [27].Baraa Kasim Mohammed and Enaam Ismail Yousif.,(Synthesis, Structural Characterisation and Biological Activity; New Metal Complexes Derived from Semicarbazone Ligand)., Revis Bionatur.,Volume 8 / Issue 2 / 14 /2023

    [28]. Sharghi H, Jokar M (2009) Highly stereo selective facile synthesis of β-amino carbonyl compounds via a Mannich-type reaction catalyzed by γ-Al2O3/MeSO3H (alumina/methanesulfonic acid: AMA) as a recyclable, efficient, and versatile heterogeneous catalyst, Can. J. Chem., 88: 14-26.

    [29]. Hasan A. Hasan, Enaam I. Yousif, Mohamad J. Al-Jeboori.,Metal-assisted assembly of dinuclear metal(II) dithiocarbamate Schiff-base macrocyclic complexes: Synthesis and biological studies.,2012 Global Journal of Inorganic Chemistry.,1,2, 132-138

    [30].Lever ABP (1984) Inorganic Electronic Spectroscopy, 2nd Ed., New York,.

    [31]. Singh RV, Dwivedi R, Joshi SC (2004) Synthetic, magnetic, spectral, antimicrobial and antifertility studies of dioxomolybdenum(VI) unsymmetrical imine complexes having a 𝑁 ∩ 𝑁 donor system, Transition Met. Chem., 29(1): 70- 74.

    [32]. Ramesh R, Maheswaran S (2003) Synthesis, spectra, dioxygen affinity and antifungal activity of Ru(III) Schiff base complexes, J. Inorg .Biochem., 96: 457-462.

    [33]. Rahman A, Choudhary M, Thomsen W (2001) Bioassay Techniques for Drug Development, Harwood Academic.

    [34].Enaam I. Y., New mixed ligand complexes; Synthesis, spectral analysis and biological   activity(2019).,Journal of Global Pharma Technology,11(2), pp. 196–203.

    [35].Hala Mohammed Salh  and Taghreed H Al-Noor.,Preparation, Structural Characterization and Biological Activities of Curcumin-Metal(II)-L-3,4-dihydroxyphenylalanin(L-dopa)complexes, Ibn Al-Haitham Journal for Pure and Applied Sciences, 36(1)2023

    [36].Amer J. Jarad a, Marwa Ali Dahi a, Taghreed H. Al-Noor a, Marei M. El-ajaily b, Salam R. AL-Ayash a, AlyAbdou c, ( Synthesis, spectral studies, DFT, biological evaluation, molecular docking and dyeing performance of 1-(4-((2-amino-5-methoxy)diazenyl)phenyl) ethanone complexes with some metallic ions)  Journal of Molecular Structure, 1287 (2023) 135703

    [37]. Baidaa K Al-Rubaye, Nasry Jassim Hussien, Abdul Salam A Abul Rahman, Siti Fairus M Yusoff, Enaam I Yousif, Mohamad J Al-Jeboori.,NEW ORGANOTIN(IV) COMPLEXES DERIVED FROM 3,4- DIHYDROXYBENZALDEHYDEN(4)-ETHYL-3-SEMICARBAZONE LIGAND : SYNTHESIS, CHARACTERISATION AND BIOLOGICAL ACTIVITY., Biochem. Cell. Arch. Vol. 20, No. 2, pp. 6571-6579, 2020.

    [38]. Mohamad J. Al-Jeboori and Safaudeen A. Hussain,. New Metal Complexes Derived from Mannich-Base Ligand; Synthesis, Spectral Characterisation and Biological Activity., | Journal of Global Pharma Technology|2019| Vol. 11| Issue 02 (Suppl.) |548-560.