Synthesis, Thermal Analysis, and Thermodynamic Properties Study of New Quinoline Derivative and Their V(IV), Co(II), and Cu(II) Complexes

https://doi.org/10.22146/ijc.74423

Raghad Jawad Kadhim Aldoghachi(1), Faris Abdulridha Jassim Aldoghachi(2*), Tahseen Abdul Qader Alsalim(3), Mohd Lokman Ibrahim(4)

(1) Department of Pharmaceutical Chemistry, University of Basrah, 61004, Basrah, Iraq
(2) Department of Chemistry, Faculty of Science, University of Basrah, 61004, Basrah, Iraq
(3) Department of Chemistry, Faculty of Education, University of Basrah, 61004, Basrah, Iraq
(4) School of Chemistry and Environment, Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Selangor 40450, Malaysia
(*) Corresponding Author

Abstract


A new ligand (E)-2-((2-chloro-6-methylquinoline-3-yl)methylene)-N'-((E)-(2-chloro-6-methylquinoline-3-yl)methylene)hydrazine-1-carbothiohydrazide (QH) was prepared by reacting hydrazine hydrate with carbon disulfide to yield thiocarbohydrazide. The thiocarbohydrazide in the second step was treated with a quinoline derivative 2-chloro-6-methylquinoline-3-carbaldehyde to yield the ligand. The ligand was identified by spectroscopic techniques FTIR, 1H-NMR, and 13C-NMR. Next, vanadium (V), cobalt (Co), and copper (Cu) complexes were prepared in the [M:L] ratio of 1:1 (QV, QCo, QCu). The complexes were characterized using FTIR, ESI, magnetic susceptibility, and molar conductivity. The thermal analysis (TGA) of V(IV), Co(II), and Cu(II) complexes were studied. The activation thermodynamic parameters, such as the energy of activation, enthalpy, entropy, and free energy change of the complexes, were evaluated, and the stabilities of the thermal decomposition of the complexes were discussed.

Keywords


quinoline derivative; thiocarbohydrazide; metal complexes; thermodynamic parameters



References

[1] Kaya, Y., Erçağ, A., and Kaya, K, 2018, Synthesis, characterization and antioxidant activities of dioxomolybdenum(VI) complexes of new Schiff bases derived from substituted benzophenones, J. Coord. Chem., 71 (20), 3364–3380.

[2] Kareem, M.J., Al-Hamdani, A.A.S., Ko, Y.G., Al Zoubi, W., and Mohammed, S.G., 2021, Synthesis, characterization, and determination antioxidant activities for new Schiff base complexes derived from 2-(1H-indol-3-yl)-ethylamine and metal ion complexes, J. Mol. Struct., 1231, 129669.

[3] Burrows, A.D., Menzer, S., Mingos, D.M.P., White, A.J., and Williams, D.J., 1997, The influence of the chelate effect on supramolecular structure formation: Synthesis and crystal structures of zinc thiourea and thiosemicarbazide complexes with terephthalate, J. Chem. Soc., Dalton Trans., 22, 4237–4240.

[4] Shaalan, N., Khalaf, W.M., and Mahdi, S, 2022, Preparation and characterization of new tetra-dentate N2O2 Schiff base with some of metal ions complexes, Indones. J. Chem., 22 (1), 62–71.

[5] Al-Saadawy, N.H., 2022, Synthesis, characterization, and theoretical study of some new organotellurium compounds derived from camphor, Indones. J. Chem., 22 (2), 437–445.

[6] Al-Saadawy, N.H., 2021, Synthesis, characterization, and theoretical studies of new organotellurium compounds based on (4-(((1S, E)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)phenyl)mercury(II) chloride, Indones. J. Chem., 21 (6), 1443–1453.

[7] Jirjees, V.Y., Al‐Hamdani, A.A.S., Wannas, N.M., Farqad, A.R, Dib, A., and Al Zoubi, W, 2021, Spectroscopic characterization for new model from Schiff base and its complexes, J. Phys. Org. Chem., 34 (4), e4169.

[8] Božić, A.R., Bjelogrlić, S.K., Novaković, I.T., Filipović, N.R., Petrović, P.M., Marinković, A.D., Todorović, T.R., and Cvijetić, I.N., 2018, Antimicrobial activity of thiocarbohydrazones: Experimental studies and alignment‐independent 3D QSAR models, ChemistrySelect, 3 (7), 2215–2221.

[9] Božić, A., Marinković, A., Bjelogrlić, S., Todorović, T.R., Cvijetić, I.N., Novaković, I., Muller, C.D., and Filipović, N.R., 2016, Quinoline based mono-and bis-(thio)carbohydrazones: Synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models, RSC Adv., 6 (106), 104763–104781.

[10] Mojallal-Tabatabaei, Z., Foroumadi, P., Toolabi, M., Goli, F., Moghimi, S., Kaboudanian-Ardestani, S., and Foroumadi, A., 2019, 2-(Bipiperidin-1-yl)-5-(nitroaryl)-1,3,4-thiadiazoles: Synthesis, evaluation of in vitro leishmanicidal activity, and mechanism of action, Bioorg. Med. Chem., 27 (16), 3682–3691.

[11] Neunhoeffer, H., and Wiley, P.F., 2009, The Chemistry of Heterocyclic Compounds: Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines, and Pentazin, Vol. 33, Wiley-Interscience, Hoboken, US.

[12] Obaid, S.M.H., Sultan, J.S., and Al-Hamdani, A.A.S., 2020, Synthesis, characterization and biological efficacies from some new dinuclear metal complexes for base 3-(3,4-dihydroxy-phenyl)-2-[(2-hydroxy-3-methylperoxy-benzylidene)-amino]-2-methyl propionic acid, Indones. J. Chem., 20 (6), 1311–1322.

[13] Shaalan, N., Abed, A.Y., Alkubaisi, H.M., and Mahde, S., 2019, Synthesis, spectroscopy, biological activities and thermodynamic studies for new complexes of some lanthanide metals with Schiff's bases derived from [2-acetylthiophene] with [2,5-dihydrazino-1,3,4-thiadiazole], Res. J. Chem. Environ., 23, 181–187.

[14] Shaalan, N.D., and Abdulwahhab, S.M., 2021, Synthesis, characterization and biological activity study of some new metal complexes with Schiff’s bases derived from [o-vanillin] with [2-amino-5-(2-hydroxy-phenyl)-1,3,4-thiadiazole], Egypt. J. Chem., 8 (8), 4059–4067.

[15] Al-Obaidy, G., Ibraheem, K.R., and Mesher, M.F., 2020, Synthesis and characterization of some new Cu II, Co II, Ni II, Au III potassium 2-(2,4-dinitrophenyl)hydrazine-1-carbodithioate complexes and evaluation of their biological activity, Int. J. Pharm. Res., 12 (1), 1025–1032.

[16] Obaid, S.M.H., Jarad, A.J., and Al-Hamdani, A.A.S., 2020, Synthesis, characterization and biological activity of mixed ligand metal salts complexes with various ligands, J. Phys.: Conf. Ser., 1660, 012028.

[17] Abdulnabi, Z.A., Al-doghachi, F.A.J., and Abdulsahib, H.T., 2021, Synthesis, characterization and thermogravimetric study of some metal complexes of selenazone ligand nanoparticles analogue of dithizone, Indones. J. Chem., 21 (5), 1231–1243.

[18] Deligeorgiev, T., Gadjev, N., Vasilev, A., Kaloyanova, S., Vaquero, J.J., and Alvarez-Builla, J., 2010, Green chemistry in organic synthesis, Mini-Rev. Org. Chem., 7 (1), 44–53.

[19] Jasim, A.M., 2011, Preparation and characterization of novel 3-(4-chloro phenyl)-1-nitro phenyl-5-(substituted phenyl)-formazans, J. Basrah Res., 37 (5), 90–98.

[20] Morrison, M.D., Hanthorn, J.J., and Pratt, D.A., 2009, Synthesis of pyrrolnitrin and related halogenated phenylpyrroles, Org. Lett., 11 (5), 1051–1054.

[21] Tiekink, E.R.T., 2018, Competing supramolecular interactions in crystals of heavy-element compounds–a consideration of the energies of association between molecules, 2nd Southeast Asian Conference on Crystal Engineering (SEACCE-2), Sunway University, Selangor, August 6-8th, 2018.

[22] Alsalim, T.A., Hadi, J.S., Ali, O.N., Abbo, H.S., and Titinchi, S.J.J., 2013, Oxidation of benzoin catalyzed by oxovanadium (IV) Schiff base complexes, Chem. Cent. J., 7 (1), 3.

[23] Zajdel, P., Partyka, A., Marciniec, K., Bojarski, A.J., Pawlowski, M., and Wesolowska, A., 2014, Quinoline- and isoquinoline-sulfonamide analogs of aripiprazole: Novel antipsychotic agents?, Future Med. Chem., 6 (1), 57–75.

[24] Shim, J.O., Jeong, D.W., Jang, W.J., Jeon, K.W., Jeon, B.H., Kim, S.H., Roh, H.S., Na, J.G., Han, S.S., and Ko, C.H., 2016, Bio-diesel production from deoxygenation reaction over Ce0.6Zr0.4O2 supported transition metal (Ni, Cu, Co, and Mo) catalysts, J. Nanosci. Nanotechnol., 16 (5), 4587–4592.

[25] Ebrahimi, H.P., Hadi, J.S., Abdulnabi, Z.A., and Bolandnazar, Z, 2014, Spectroscopic, thermal analysis and DFT computational studies of salen-type Schiff base complexes, Spectrochim. Acta, Part A, 117, 485–492.



DOI: https://doi.org/10.22146/ijc.74423

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