Proceedings of International Conference on Applied Innovation in IT
2025/06/27, Volume 13, Issue 2, pp.635-642
Synthesis Structural Study and Spectroscopic Characterization of Azo Compound Derived from Mercaptothiadiazole and Methoxybenzaldehyde
Ghalib A. Atiya, Nada J. Khadm, Abd-Karim Fadhil Ali, Waseela Abdul Redha Abdul Razaq, Abdulqadier Hussian Neamal and Ibtsiam Khalil Alwan Abstract: The vibrational and electronic properties of 2-hydroxy-5-((5-mercapto-1,3,4-thiadiazol-2-yl)diazenyl)-3-methoxy benzaldehyde were theoretically studied in the present paper by carrying out quantum chemical calculations. Vibrational wavenumbers and their respective assignments were computed at the Hartree-Fock and DFT/B3LYP levels with the 6-311++G(d,p) basis set using Gaussian03 software. The theoretical IR and Raman spectra were calculated and compared with the experimental IR spectrum, which showed good agreement. The vibrational assignments were made by PEG analysis to ensure proper characterization of the modes. Theoretical IR and Raman intensities have also been calculated to provide further spectroscopic insight. Frontier molecular orbitals have been estimated to obtain an in-depth analysis of the electronic structure. (FMOs) were analyzed. The HOMO and LUMO energies have been computed thereby giving HOMO–LUMO energy which, in turn, gives insight into the reactivity and stability of the molecule. Also, Mulliken charges and Molecular Electrostatic Potential (MEP) analysis were computed for charge transfer character and electrostatic interaction within the molecule, respectively. This study is also supplemented by Natural Bond Orbital (NBO) analysis of charges to investigate intramolecular and intermolecular charge delocalization effects on their mean stabilization interactions in the system. Thus, it can parse from the electronic and vibrational features that it can be useful in spectroscopic applications further in molecular design. The paper would, therefore, reveal the power that computational chemistry brings in the prediction and interpretation of vibrational and electronic properties that would go a long way to unravel compounds structurally similar to the heterocyclic compound.
Keywords: azoaldehyde , o-vanillin , IR, Gussian, vibration, bending.
DOI: 10.25673/120551
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References:
- V.M. Dembitsky, T.A. Gloriozova and V.V. Poroikov, "Pharmacological and predicted activities of natural azo compounds," Natural Products and Bioprospecting, vol. 7, pp. 151-169, 2017.
- A.Z. El-Sonbati, G.G. Mohamed, A.A. El-Bindary, W.M.I. Hassan and A.K. Elkholy, "Geometrical structure, molecular docking, potentiometric and thermodynamic studies of 3-aminophenol azodye and its metal complexes," Journal of Molecular Liquids, vol. 209, pp. 625-634, 2015.
- A.A. El-Bindary, M.A. Hussein and R.A. El-Boz, "Molecular docking, theoretical calculations and potentiometric studies of some azo phenols," Journal of Molecular Liquids, vol. 211, pp. 256-267, 2015.
- E.M. Zayed, A.M. Hindy and G.G. Mohamed, "Molecular structure, molecular docking, thermal, spectroscopic and biological activity studies of bis Schiff base ligand and its metal complexes," Applied Organometallic Chemistry, vol. 32, no. 1, p. e3952, 2018.
- H.A. Hasan, W.M. Alwan, R.M. Ahmed and E.I. Yousif, "Synthesis and characterization of some mixed-ligand complexes containing azo dye and 1,10-phenanthroline with (CoII, ZnII, CdII and HgII ions)," Ibn Al-Haitham Journal for Pure & Applied Sciences, vol. 28, no. 3, pp. 187-203, 2015.
- T.R. Arun and N. Raman, "Antimicrobial efficacy of phenanthrenequinone based Schiff base complexes incorporating methionine amino acid: Structural elucidation and in vitro bio assay," Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 127, pp. 292-302, 2014.
- J. Bell, J.J. Plumb, C.A. Buckley and D.C. Stuckey, "Treatment and decolorization of dyes in an anaerobic baffled reactor," Journal of Environmental Engineering, vol. 126, no. 11, pp. 1026-1032, 2000.
- K.T. Chung, "Azo dyes and human health: A review," Journal of Environmental Science and Health, Part C, vol. 34, no. 4, pp. 233-261, 2016.
- S. Benkhaya, S. M’rabet and A. El Harfi, "Classifications, properties, recent synthesis and applications of azo dyes," Heliyon, vol. 6, no. 1, 2020.
- A.A. Ismail and S.M. Lateef, "Synthesis of novel complexes of VO(II), Mn(II), Fe(II), Co(II), Ni(II), Cu(II) and Pt(IV) derived from Schiff’s base of pyridoxal and 2-amino-4-nitrophenol and study of their biological activities," Ibn Al-Haitham Journal for Pure and Applied Sciences, vol. 36, no. 2, pp. 259-275, 2023.
- B.K. Mohammed and E.I. Yousif, "Synthesis, structural characterisation and biological activity of new metal complexes derived from semicarbazone ligand," Revis Bionatur, vol. 8, no. 2, p. 14, 2023.
- A. Tupys, J. Kalembkiewicz, Y. Ostapiuk, V. Matiichuk, O. Tymoshuk, E. Woźnicka and Ł. Byczyński, "Synthesis, structural characterization and thermal studies of a novel reagent 1-[(5-benzyl-1,3-thiazol-2-yl) diazenyl] naphthalene-2-ol," Journal of Thermal Analysis and Calorimetry, vol. 127, pp. 2233-2242, 2017.
- A. Penchev, D. Simov and N. Gadjev, "Diazotization of 2-amino-6-methoxybenzothiazole at elevated temperature," Dyes and Pigments, vol. 16, no. 1, pp. 77-81, 1991.
- G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, "Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases," European Journal of Medicinal Chemistry, vol. 43, no. 12, pp. 2639-2649, 2008.
- M.J. Al-Jeboori, A.T. Numan and D.J. Ahmed, "Synthesis and Characterisation of Novel Cobalt(II), Copper(II) and Mercury(II) Complexes of Poly Vinyl Urethanised Oxime," Ibn Al-Haitham Journal for Pure and Applied Sciences, vol. 21, no. 2, pp. 89-101, 2017.
- S.A. Hussain and M.J. Al-Jeboori, "New metal complexes derived from Mannich-base ligand; Synthesis, spectral characterisation and biological activity," Journal of Global Pharma Technology, vol. 11, no. 2, pp. 548-560, 2019.
- E. Ramachandran, V. Gandin, R. Bertani, P. Sgarbossa, K. Natarajan, N.S. Bhuvanesh, A. Venzo, A. Zoleo, A. Glisenti, A. Dolmella and A. Albinati, "Synthesis, characterization and cytotoxic activity of novel copper(II) complexes with aroylhydrazone derivatives of 2-oxo-1,2-dihydrobenzo[h]quinoline-3-carbaldehyde," Journal of Inorganic Biochemistry, vol. 182, pp. 18-28, 2018.
- A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd ed., 1984.
- R. Ramesh and S. Maheswaran, "Synthesis, spectra, dioxygen affinity and antifungal activity of Ru(III) Schiff base complexes," Journal of Inorganic Biochemistry, vol. 96, pp. 457-462, 2003.
- N. Aggarwal, R. Kumar, P. Dureja and D.S. Rawat, "Schiff bases as potential fungicides and nitrification inhibitors," Journal of Agricultural and Food Chemistry, vol. 57, no. 18, pp. 8520-8525, 2009.
- B.K. Al-Rubaye, M.J. Al-Jeboori and H. Potgieter, "Metal Complexes of Multidentate N2S2 Heterocyclic Schiff-base Ligands; Formation, Structural Characterisation and Biological Activity," Journal of Physics: Conference Series, vol. 1879, no. 2, p. 022074, 2021.
- C. Liu, W. Zhang and G. Cai, "Synthesis, crystal structures and catalytic activities of two copper coordination compounds bearing an N,N’-dibenzylethylenediamine ligand," Crystals, vol. 10, no. 6, p. 528, 2020.
- A.C. Olivieri, R.B. Wilson, I.C. Paul and D.Y. Curtin, "Carbon-13 NMR and x-ray structure determination of 1-(arylazo)-2-naphthols. Intramolecular proton transfer between nitrogen and oxygen atoms in the solid state," Journal of the American Chemical Society, vol. 111, no. 15, pp. 5525-5532, 1989.
- M.J. Al-Jeboori, E.I. Abdulkarim and S. Attia, "Synthesis and Characterization of Novel Ligand Type N2O2 and its Complexes with Cu(II), Co(II), Ni(II), Zn(II), and Cd(II) ions," Ibn Al-Haitham Journal for Pure and Applied Sciences, vol. 18, no. 2, pp. 51-67, 2015.
- H.J. Abaas and M.J. Al-Jeboori, "New dimeric complexes with semicarbazone Mannich-based ligand; formation, structural investigation and biological activity," Rev. Bionatura, vol. 8, no. 2, p. 15, 2023.
- J. Conradie, M.M. Conradie, Z. Mtshali, D. van der Westhuizen, K.M. Tawfiq, M.J. Al-Jeboori, S.J. Coles, C. Wilson and J.H. Potgieter, "Synthesis, characterisation and electrochemistry of eight Fe coordination compounds containing substituted 2-(1-(4-R-phenyl-1H-1,2,3-triazol-4-yl)pyridine ligands, R = CH3, OCH3, COOH, F, Cl, CN, H and CF3," Inorg. Chim. Acta, vol. 484, pp. 375-385, 2019.
- P.M. Tolstoy, J. Guo, B. Koeppe, N.S. Golubev, G.S. Denisov, S.N. Smirnov and H.H. Limbach, "Geometries and tautomerism of OHN hydrogen bonds in aprotic solution probed by H/D isotope effects on 13C NMR chemical shifts," The Journal of Physical Chemistry A, vol. 114, no. 40, pp. 10775-10782, 2010.
- L. Guasch, W. Yapamudiyansel, M.L. Peach, J.A. Kelley, J.J. Barchi Jr. and M.C. Nicklaus, "Experimental and chemoinformatics study of tautomerism in a database of commercially available screening samples," Journal of Chemical Information and Modeling, vol. 56, no. 11, pp. 2149-2161, 2016.
- L. Racane, Z. Mihalić, H. Cerić, J. Popović and V. Tralić-Kulenović, "Synthesis, structure and tautomerism of two benzothiazolyl azo derivatives of 2-naphthol: A crystallographic, NMR and computational study," Dyes and Pigments, vol. 96, no. 3, pp. 672-678, 2013.
- H. Kocaokutgen and E. Erdem, "Synthesis and spectral characterization of metal complexes of 1-(2-hydroxy-4-methylphenylazo)-2-naphthol," Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 34, no. 10, pp. 1843-1853, 2004.
- K.Y. Law, I.W. Tarnawskyj and P.T. Lubberts, "Azo pigments and their intermediates: Effect of substitution on the diazotization and coupling reactions of o-hydroxyanilines," Dyes and Pigments, vol. 23, no. 4, pp. 243-254, 1993.
- A.J. Jarad, M.A. Dahi, T.H. Al-Noor, M.M. El Ajaily, S.R. Al-Ayash and A. Abdou, "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, vol. 1287, p. 135703, 2023.
- E.J. Baron and S.M. Finegold, Diagnostic Microbiology, 8th ed., London: Mosby Company, 1990, pp. 53-62.
- S.A. Hussein and E.I. Yousif, "New mannich base (2R)-4-methyl-2-((S)(phenylamino)(p-tolyl)methyl)cyclohexan-1-one; synthesis and spectral characterisation," Journal of Physics: Conference Series, vol. 1, p. 012019, 1999.
- R.V. Singh, R. Dwivedi and S.C. Joshi, "Synthetic, magnetic, spectral, antimicrobial and antifertility studies of dioxomolybdenum(VI) unsymmetrical imine complexes having a N∩N donor system," Transition Metal Chemistry, vol. 29, no. 1, pp. 70-74, 2004.
- H.M. Salh and T.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, vol. 36, no. 1, 2023.
- A.S.A.K.A. Rahman, N.J. Hussien, K.T. Abdullah, S.F.M. Yusof and E.I. Yousif, "Synthesis, characterization and antibacterial activity of some transition metal complexes of a new dioxime ligand," AIP Conference Proceedings, vol. 2593, p. 060001, 2023.
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