Abstract
The thiazole carbamothioyl benzamide derivative (H2L) and its complexes with Mn(II), Cu(II), and Ni(II), are discussed in this study. The reaction between benzoyl isothiocyanate and benzo[d]thiazol-2-amine produced the thiazole carbamothioyl benzamide moiety. Analytical, spectroscopic, and magnetic studies were used to clarify the structures of these substances. DFT confirmed the octahedral construction of all complexes. Thiazole carbamothioyl benzamide metal complex thermal degradation behavior was investigated. The kinetics for all studied compounds (Ea, A, ΔG*, ΔS*, and ΔH*) have been calculated from thermal degradation phases. Effective inhibitory action of the H2L in comparison to other examined compounds was shown by ABTS-antioxidant activities and cytotoxicity towards liver (HePG2) and breast (MCF-7) carcinoma cells. Ni(II) complex has the most activity against C. albicans fungal stain and Cu(II) proved to have the best activity against E. Coli and S. aureus bacterial stains. The binding affinity between the substances under study and the HepG-2 (PDB ID: 2OH4) and MCF-7 (PDB ID: 3W2S) proteins was also determined using the Schrödinger suite program.
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Abbas, S.Y., Al-Harbi, R.A., El-Sharief, M.A.S.: Synthesis and anticancer activity of thiourea derivatives bearing a benzodioxole moiety with EGFR inhibitory activity, apoptosis assay and molecular docking study. Eur. J. Med. Chem. 198, 112363 (2020). https://doi.org/10.1016/j.ejmech.2020.112363
Abdullaha, M., Nuthakki, V.K., Bharate, S.B.: Discovery of methoxy-naphthyl linked N-(1-benzylpiperidine) benzamide as a blood-brain permeable dual inhibitor of acetylcholinesterase and butyrylcholinesterase. Eur. J. Med. Chem. 207, 112761 (2020). https://doi.org/10.1016/j.ejmech.2020.112761
Abu El-Reash, G.M., El-Gammal, O.A., El-Gamil, M.M.: Structural, spectral, DFT, pH-metric and biological studies on Cr(III), Mn(II) and Fe(III) complexes of dithione heterocyclic thiosemicarbazide ligand. Spectrochim Acta, A 104, 383–393 (2013). https://doi.org/10.1016/j.saa.2012.11.070
Abu El-Reash, G.M., El-Gammal, O.A., Ghazy, S.E., Radwan, A.H.: Characterization and biological studies on Co (II), Ni (II) and Cu (II) complexes of carbohydrazones ending by pyridyl ring. Spectrochim Acta, A 104, 26–34 (2013). https://doi.org/10.1016/j.saa.2012.11.008
Abu El-Reash, G.M., Ibrahim, K.M., Bekheit, M.M.: Ligational behaviour of biacetylmonoxime nicotinoyl hydrazone (H2BMNH) towards transition metal ions. Transit. Met. Chem. 15(2), 148–151 (1990). https://doi.org/10.1007/BF01023905
Ahmed, A., Shafique, I., Saeed, A., Shabir, G., Saleem, A., Taslimi, P., et al.: Nimesulide linked acyl thioureas potent carbonic anhydrase I, II and α-glucosidase inhibitors: design, synthesis and molecular docking studies. Eur. J. Med. Chem.Rep. 6, 100082 (2022). https://doi.org/10.1016/j.ejmcr.2022.100082
Al-Adilee, K.J., Shaimaa, A.: Synthesis and spectral properties studies of novel hetrocyclic mono azo dye derived from thiazole and pyridine with some transition complexes. Orient. J. Chem. 33(4), 1–14 (2017). https://doi.org/10.13005/ojc/330426
Al-Farraj, E.S., Fetoh, A.: Synthesis of new Fe(III), Co(II), and Cr(III) complexes of N-(benzo[d]thiazol-2-ylcarbamothioyl)benzamide (H2L2): structural characterization and biological activities. Appl. Organomet. Chem. (2023). https://doi.org/10.1002/aoc.7248
Al-Qahtani, S.D., Alharbi, A., Abualnaja, M.M., Hossan, A., Alhasani, M., Abu-Dief, A.M., et al.: Synthesis and elucidation of binuclear thiazole-based complexes from Co(II) and Cu(II) ions: conductometry, cytotoxicity and computational implementations for various verifications. J. Mol. Liq. 349, 118100 (2022). https://doi.org/10.1016/j.molliq.2021.118100
Aljahdali, M., El-Sherif, A.A.: Synthesis, characterization, molecular modeling and biological activity of mixed ligand complexes of Cu (II), Ni (II) and Co (II) based on 1, 10-phenanthroline and novel thiosemicarbazone. Inorg. Chim. Acta 407, 58–68 (2013). https://doi.org/10.1016/j.ica.2013.06.040
Anliker, R.: Ecotoxicology of dyestuffs—a joint effort by industry. Ecotoxicol. Environ. Saf. 3(1), 59–74 (1979). https://doi.org/10.1016/0147-6513(79)90060-5
Asiri, Y.I., Alsayari, A., Muhsinah, A.B., Mabkhot, Y.N., Hassan, M.Z.: Benzothiazoles as potential antiviral agents. J. Pharm. Pharmacol. 72(11), 1459–1480 (2020). https://doi.org/10.1111/jphp.13331
Chubar, N., Carvalho, J.R., Correia, M.J.N.: Cork biomass as biosorbent for Cu (II), Zn (II) and Ni (II). Colloids Surf., A 230(1), 57–65 (2003). https://doi.org/10.1016/j.colsurfa.2003.09.014
Chung, K.-T., Stevens, S.E., Jr.: Degradation azo dyes by environmental microorganisms and helminths. Environ. Toxicol. Chem. 12(11), 2121–2132 (1993). https://doi.org/10.1002/etc.5620121120
Cipriano, L.A., Di Liberto, G., Tosoni, S., Pacchioni, G.: Band gap in magnetic insulators from a charge transition level approach. J. Chem. Theory Comput. 16(6), 3786–3798 (2020). https://doi.org/10.1021/acs.jctc.0c00134
Coats, A.W., Redfern, J.P.: Kinetic parameters from thermogravimetric data. Nature 201(4914), 68–69 (1964). https://doi.org/10.1038/201068a0
de Fátima, Â., de Paula Pereira, C., Olímpio, C.R.S.D.G., de Freitas Oliveira, B.G., Franco, L.L., da Silva, P.H.C.: Schiff bases and their metal complexes as urease inhibitors–a brief review. J. Adv. Res. 13, 113–126 (2018). https://doi.org/10.1016/j.jare.2018.03.007
Delley, B.: Hardness conserving semilocal pseudopotentials. Phys. Rev. B Condens. Matter 66(15), 155125 (2002). https://doi.org/10.1103/PhysRevB.66.155125
Drzewiecka-Antonik, A., Rejmak, P., Klepka, M.T., Wolska, A., Pietrzyk, P., Stępień, K., et al.: Synthesis, structural studies and biological activity of novel Cu (II) complexes with thiourea derivatives of 4-azatricyclo [5.2. 1.02, 6] dec-8-ene-3, 5-dione. J. Inorg. Biochem. 176, 8–16 (2017). https://doi.org/10.1016/j.jinorgbio.2017.08.001
El-Gammal, O., El-Reash, G.A., Ghazy, S., Radwan, A.: Synthesis, characterization, molecular modeling and antioxidant activity of (1E, 5E)-1, 5-bis (1-(pyridin-2-yl) ethylidene) carbonohydrazide (H2APC) and its zinc (II), cadmium (II) and mercury (II) complexes. J. Mol. Struct. 1020, 6–15 (2012). https://doi.org/10.1016/j.molstruc.2012.04.029
El-Gammal, O.A.: Synthesis, characterization, molecular modeling and antimicrobial activity of 2-(2-(ethylcarbamothioyl) hydrazinyl)-2-oxo-N-phenylacetamide copper complexes. Spectrochim. Acta, A 75(2), 533–542 (2010). https://doi.org/10.1016/j.saa.2009.11.007
El-Metwaly, N., Farghaly, T.A., Elghalban, M.G.: Synthesis, analytical and spectral characterization for new VO (II)-triazole complexes; conformational study beside MOE docking simulation features. Appl. Organomet. Chem. 34(4), e5505 (2020). https://doi.org/10.1002/aoc.5505
El-Morshedy, R.M., El-Gamil, M.M., Abou-Elzahab, M.M., Abu El-Reash, G.M.: Spectroscopic investigation, DFT, fluorescence, molecular docking and biological studies of divalent and trivalent binuclear complexes prepared from benzoyl thiosemicarbazide derivative of 2-benzylmalonohydrazide. Appl. Organomet. Chem. 33(5), e4871 (2019). https://doi.org/10.1002/aoc.4871
El-Sayed, M.A.-A., El-Husseiny, W.M., Abdel-Aziz, N.I., El-Azab, A.S., Abuelizz, H.A., Abdel-Aziz, A.A.-M.: Synthesis and biological evaluation of 2-styrylquinolines as antitumour agents and EGFR kinase inhibitors: molecular docking study. J. Enzyme Inhib. Med. Chem. 33(1), 199–209 (2018). https://doi.org/10.1080/14756366.2017.1407926
Emam, S.M., Tolan, D.A., El-Nahas, A.M.: Synthesis, structural, spectroscopic, and thermal studies of some transition-metal complexes of a ligand containing the amino mercapto triazole moiety. Appl. Organomet. Chem. 34(5), e5591 (2020). https://doi.org/10.1002/aoc.5591
Etaiw, S.E.D.H., Fayed, T.A., El-bendary, M.M., Marie, H.: Three-dimensional coordination polymers based on trimethyltin cation with nicotinic and isonicotinic acids as anticancer agents. Appl. Organomet. Chem. 32(2), e4066 (2018). https://doi.org/10.1002/aoc.4066
Fakhar, I., Yamin, B. M., Hasbullah, S. A.: Synthesis and characterization of bis-thiourea having amino acid derivatives. Paper presented at the AIP Conference Proceedings (2016)
Ferraro, J., Walker, W.: Infrared spectra of hydroxy-bridged copper (II) compounds. Inorg. Chem. 4(10), 1382–1386 (1965). https://doi.org/10.1021/ic50032a002
Fukui, K., Yonezawa, T., Nagata, C., Shingu, H.: Molecular orbital theory of orientation in aromatic, heteroaromatic, and other conjugated molecules. J. Chem. Phys. 22(8), 1433–1442 (1954). https://doi.org/10.1063/1.1740412
Gaber, M., El-Ghamry, H.A., Fathalla, S.K.: Synthesis, structural identification, DNA interaction and biological studies of divalent Mn, Co and Ni chelates of 3-amino-5-mercapto-1,2,4-triazole azo ligand. Appl. Organomet. Chem. 34(4), e5678 (2020). https://doi.org/10.1002/aoc.5678
Gaber, M., Fayed, T.A., El-Gamil, M.M., El-Reash, G.M.A.: Structural, thermogravimetric, B3LYP and biological studies on some heterocyclic thiosemicarbazide copper (II) complexes and evaluation of their molecular docking. J. Mol. Struct. 1151, 56–72 (2018). https://doi.org/10.1016/j.molstruc.2017.09.035
Garg, B.S., Kurup, M.P., Jain, S.K., Bhoon, Y.K.: Manganese (II) complexes of substituted thio-and selenosemicarbazones of 2-acetylpyridine: ESR, magnetic and electronic spectral studies. Transit Met. Chem. 13(2), 92–95 (1988). https://doi.org/10.1007/BF01087795
Govindarajan, M., Periandy, S., Carthigayen, K.: FT-IR and FT-Raman spectra, thermo dynamical behavior, HOMO and LUMO, UV, NLO properties, computed frequency estimation analysis and electronic structure calculations on α-bromotoluene. Spectrochim. Acta, Part A 97, 411–422 (2012)
Hammer, B., Hansen, L.B., Nørskov, J.K.: Improved adsorption energetics within density-functional theory using revised Perdew–Burke–Ernzerhof functionals. Phys. Rev. B Condens. Matter 59(11), 7413 (1999). https://doi.org/10.1103/PhysRevB.59.7413
Han, M.H., Yun, Y.-S.: Mechanistic understanding and performance enhancement of biosorption of reactive dyestuffs by the waste biomass generated from amino acid fermentation process. Biochem. Eng. J. 36(1), 2–7 (2007). https://doi.org/10.1016/j.bej.2006.06.010
Hathaway, B.J., Billing, D.E.: The electronic properties and stereochemistry of mono-nuclear complexes of the copper (II) ion. Coord. Chem. Rev. 5(2), 143–207 (1970). https://doi.org/10.1016/S0010-8545(00)80135-6
Horowitz, H.H., Metzger, G.: A new analysis of thermogravimetric traces. Anal. Chem. 35(10), 1464–1468 (1963). https://doi.org/10.1021/ac60203a013
Hosny, N.M., Hussien, M.A., Motawa, R., Belal, A., Abdel-Rhman, M.H.: Synthesis, spectral, modeling, docking and cytotoxicity Studies on 2-(2-aminobenzoyl)-N-ethylhydrazine-1-carbothioamide and its divalent metal complexes. Appl. Organomet. Chem. (2020). https://doi.org/10.1002/aoc.5922
Imran, S., Taha, M., Ismail, N.H., Fayyaz, S., Khan, K.M., Choudhary, M.I.: Synthesis, biological evaluation, and docking studies of novel thiourea derivatives of bisindolylmethane as carbonic anhydrase II inhibitor. Bioorg. Chem. 62, 83–93 (2015). https://doi.org/10.1016/j.bioorg.2015.08.001
Jeffery, G.H., Bassett, J., Mendham, J., Denney, R.C.: vogel’s textbook of quantitative chemical analysis. John Wiley & Sons Inc, New York (1989)
Kazemi, M.: Reusable nanomagnetic catalysts in synthesis of imidazole scaffolds. Synth. Commun. 50(14), 2095–2113 (2020). https://doi.org/10.1080/00397911.2020.1728334
Kenawy, I., Hafez, M., Lashein, R.: Thermal decomposition of chloromethylated poly (styrene)-PAN resin and its complexes with some transition metal ions. J. Therm. Anal. Calorim. 65(3), 723–736 (2001). https://doi.org/10.1023/a:1011999325998
Kessi, A., Delley, B.: Density functional crystal versus cluster models as applied to zeolites. Int. J. Quantum Chem. 68(2), 135–144 (1998). https://doi.org/10.1002/(SICI)1097-461X(1998)68:2%3c135::AID-QUA6%3e3.0.CO;2-W
Khan, T.A., Ghani, S.S., Naseem, S.: Interaction of Co(II), Ni(II), Cu(II), and Zn(II) with 12- and 14-membered macrocycles containing O2N2 donors. J. Coord. Chem. 63(24), 4411–4420 (2010). https://doi.org/10.1080/00958972.2010.535524
Khatri, N., Lather, V., Madan, A.: Diverse classification models for anti-hepatitis C virus activity of thiourea derivatives. Chemom. Intell. Lab. Syst. 140, 13–21 (2015). https://doi.org/10.1016/j.chemolab.2014.10.007
Koch, A.L.: Bacterial wall as target for attack: past, present, and future research. Clin. Microbiol. Rev. 16, 673–687 (2003). https://doi.org/10.1128/cmr.16.4.673-687.2003
Lever, A.B.P.: Inorganic electronic spectroscopy. Elsevier, Amsterdam (1984)
Liu, L., Alam, M.S., Lee, D.-U.: Synthesis, Antioxidant Activity and Fluorescence Properties of Novel Europium Complexes with (E)-2-or 4-hydroxy-N′-[(2-hydroxynaphthalen-1-yl) methylene] benzohydrazide Schiff base. Bull. Korean Chem. Soc. 33(10), 3361–3367 (2012). https://doi.org/10.5012/bkcs.2012.33.10.3361
Liu, Z., Jiang, A., Wang, Y., Xu, P., Zhang, Q., Wang, Y., et al.: In silico, synthesis and anticancer evaluation of benzamide tryptamine derivatives as novel eEF2K inhibitors. Bioorg. Med. Chem. Lett. 67, 128759 (2022). https://doi.org/10.1016/j.bmcl.2022.128759
Luque, F.J., López, J.M., Orozco, M.: Perspective on electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Theor Chem Acc 103, 343–345 (2000)
Maalik, A., Rahim, H., Saleem, M., Fatima, N., Rauf, A., Wadood, A., et al.: Synthesis, antimicrobial, antioxidant, cytotoxic, antiurease and molecular docking studies of N-(3-trifluoromethyl) benzoyl-N′-aryl thiourea derivatives. Bioorg. Chem. 88, 102946 (2019). https://doi.org/10.1016/j.bioorg.2019.102946
Masoud, M.S., Ali, A.E., Shaker, M.A., Elasala, G.S.: Synthesis, computational, spectroscopic, thermal and antimicrobial activity studies on some metal–urate complexes. Spectrochim Acta, A 90, 93–108 (2012). https://doi.org/10.1016/j.saa.2012.01.028
Matesanz, A.I., Herrero, J.M., Faraco, E.J., Cubo, L., Quiroga, A.G.: New platinum(II) triazole thiosemicarbazone complexes: analysis of their reactivity and potential antitumoral action. ChemBioChem 21(8), 1226–1232 (2020). https://doi.org/10.1002/cbic.201900545
Maurya, R.C., Rajput, S.: Oxovanadium (IV) complexes of bioinorganic and medicinal relevance: synthesis, characterization, and 3D molecular modeling and analysis of some oxovanadium (IV) complexes involving O O-Donor environment. J. Mol. Struct. 687(1–3), 35–44 (2004). https://doi.org/10.1016/j.molstruc.2003.08.023
Mohan, M., Kumar, M.: Transition metal chemistry of oxime—containing ligands, Part XXVIII; manganese (II) complexes of 2, 6-diacetylpyridine dioxime. Transition Met. Chem. 10(7), 255–258 (1985). https://doi.org/10.1007/BF00621081
Moore, J.W., Pearson, R.G.: Kinetics and mechanism. John Wiley & Sons, New York (1961)
Naumov, N., Artemkina, S., Virovets, A., Fedorov, V.: Facile transformation of isolated fragments to infinite chains in rhenium chalcocyanide clusters: synthesis and structure of (Pr4N) 2M (H2O) 5 [Re6X8 (CN) 6]· H2O and (Pr4N) 2M (H2O) 4 [Re6S8 (CN) 6](X= S, Se; M= Mn, Ni). J. Solid State Chem. 153(2), 195–204 (2000)
Novak Jovanović, I., Miličević, A., Jadreško, D., Hranjec, M.: Electrochemical oxidation of synthetic amino-substituted benzamides with potential antioxidant activity. J. Electroanal. Chem. 870, 114244 (2020). https://doi.org/10.1016/j.jelechem.2020.114244
Okulik, N., Jubert, A.H.: Theoretical analysis of the reactive sites of non-steroidal anti-inflammatory drugs. Internet Electron J. Mol. Des 4(1), 17–30 (2005)
Padmanabhan, J., Parthasarathi, R., Subramanian, V., Chattaraj, P.: Electrophilicity-based charge transfer descriptor. J. Phys. Chem. A 111(7), 1358–1361 (2007). https://doi.org/10.1021/jp0649549
Pandey, R., Kumari, R., Sinha, S., Sahay, A.: Thioamide bands and nature of bonding in the metal complexes of 3-(4-pyridyl)-4-phenyl triazoline-5-thione. Asian J. Chem. 5(3), 552 (1993)
Park, H.I., Ming, L.-J.: The mechanistic role of the coordinated tyrosine in astacin. J. Inorg. Biochem. 72(1–2), 57–62 (1998). https://doi.org/10.1016/S0162-0134(98)10063-6
Parthasarathi, R., Padmanabhan, J., Subramanian, V., Sarkar, U., Maiti, B., Chattaraj, P.: Toxicity analysis of benzidine through chemical reactivity and selectivity profiles: A DFT approach. Internet Electron J. Mol. Des 2(12), 798–813 (2003)
Pearson, R.G.: Absolute electronegativity and hardness: applications to organic chemistry. J. Org. Chem. 54(6), 1423–1430 (1989). https://doi.org/10.1021/jo00267a034
Politzer, P., Laurence, P.R., Jayasuriya, K.: Molecular electrostatic potentials: an effective tool for the elucidation of biochemical phenomena. Environ. Health Perspect. 61, 191–202 (1985). https://doi.org/10.1289/ehp.8561191
Rahman, F.U., Bibi, M., Altaf, A.A., Tahir, M.N., Ullah, F., Khan, E.: Zn, Cd and Hg complexes with unsymmetric thiourea derivatives; syntheses, free radical scavenging and enzyme inhibition essay. J. Mol. Struct. 1211, 128096 (2020). https://doi.org/10.1016/j.molstruc.2020.128096
Rakha, T.H., Ibrahim, K.M., Khalifa, M.I.: Thermochemical study of some transition metal complexes of isonicotinic hydrazide derivatives. Thermochim. Acta 144(1), 53–63 (1989). https://doi.org/10.1016/0040-6031(89)85084-1
Raman, N., Sakthivel, A., Jeyamurugan, R.: Synthesis, structural characterization, antimicrobial, DNA-binding, and photo-induced DNA cleavage activity of some bio-sensitive Schiff base copper(II) complexes. J. Coord. Chem. 63(24), 4380–4397 (2010). https://doi.org/10.1080/00958972.2010.539212
Rastogi, D., Sharma, K.: Stereochemical features of some nickel (II) and cobalt (II) complexes of amino ligand—2-(2-aminoethyl) pyridine-VII. J. Inorg. Nucl. Chem. 36(10), 2219–2228 (1974). https://doi.org/10.1016/0022-1902(74)80258-7
Razak, N.H.A., Tan, L.L., Hasbullah, S.A., Heng, L.Y.: Reflectance chemosensor based on bis-thiourea derivative as ionophore for copper (II) ion detection. Microchem. J. 153, 104460 (2020). https://doi.org/10.1016/j.microc.2019.104460
Robinson, T., Chandran, B., Nigam, P.: Removal of dyes from a synthetic textile dye effluent by biosorption on apple pomace and wheat straw. Water Res. 36(11), 2824–2830 (2002). https://doi.org/10.1016/S0043-1354(01)00521-8
Sakr, A., Kothayer, H., Ibrahim, S.M., Baraka, M.M., Rezq, S.: 1,4-Dihydroquinazolin-3(2H)-yl benzamide derivatives as anti-inflammatory and analgesic agents with an improved gastric profile: Design, synthesis, COX-1/2 inhibitory activity and molecular docking study. Bioorg. Chem. 84, 76–86 (2019). https://doi.org/10.1016/j.bioorg.2018.11.030
Santos, V.P., Pereira, M.F., Faria, P.C., Orfao, J.J.: Decolourisation of dye solutions by oxidation with H(2)O(2) in the presence of modified activated carbons. J. Hazard. Mater. 162(2–3), 736–742 (2009). https://doi.org/10.1016/j.jhazmat.2008.05.090
Scrocco, E., Tomasi, J.: Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials. Adv. Quantum Chem. (1978). https://doi.org/10.1016/S0065-3276(08)60236-1
Shadap, L., Diamai, S., Tyagi, J.L., Poluri, K.M., Kaminsky, W., Kollipara, M.R.: Synthesis, biological evaluation and colorimetric sensing studies of platinum group metal complexes comprising pyrazine based thiourea derivatives. J. Organomet. Chem. 897, 207–216 (2019). https://doi.org/10.1016/j.jorganchem.2019.07.011
Shukla, A.K., Shrivash, M.K., Pandey, A., Pandey, J.: Synthesis, in vitro and computational studies of novel glycosyl-1, 2, 3–1H-triazolyl methyl benzamide derivatives as potential α-glucosidase inhibitory activity. Bioorg. Chem. 109, 104687 (2021). https://doi.org/10.1016/j.bioorg.2021.104687
Singh, H.L., Varshney, S., Varshney, A.K.: Organotin (IV) complexes of biologically active Schiff bases derived from heterocyclic ketones and sulpha drugs. Appl. Organomet. Chem. 13(9), 637–641 (1999). https://doi.org/10.1002/(SICI)1099-0739(199909)13:9%3c637::AID-AOC919%3e3.0.CO;2-K
Tossidis, I., Bolos, C., Aslanidis, P., Katsoulos, G.: Monohalogenobenzoylhydrazones III. Synthesis and structural studies of Pt(II), Pd(II) and Rh(III) complexes of Di-(2-pyridyl) ketonechlorobenzoyl hydrazones. Inorg. Chim. Acta 133(2), 275–280 (1987). https://doi.org/10.1016/S0020-1693(00)87779-8
Velumani, S., Mathew, X., Sebastian, P., Narayandass, S.K., Mangalaraj, D.: Structural and optical properties of hot wall deposited CdSe thin films. Sol. Energy Mater. Sol. Cells 76(3), 347–358 (2003). https://doi.org/10.1016/S0927-0248(02)00287-8
Warren, J.H.: Ab initio molecular orbital theory. Wiley-Interscience, New Jersey (1986)
Welleman, J.A., Hulsbergen, F.B., Verbiest, J., Reedijk, J.: Influence of alkyl chain length in N-alkyl imidazoles upon the complex formation with transition-metal salts. J. Inorg. Nucl. Chem. 40(1), 143–147 (1978). https://doi.org/10.1016/0022-1902(78)80328-5
Xun-Zhong, Z., An-Sheng, F., Fu-Ran, Z., Min-Cheng, L., Yan-Zhi, L., Meng, M., Yu, L.: Synthesis, crystal structures, and antimicrobial and antitumor studies of two zinc(II) complexes with pyridine thiazole derivatives. Bioinorg. Chem. Appl. 2020, 8852470 (2020). https://doi.org/10.1155/2020/8852470
Yahyazadeh, A., Ghasemi, Z.: Synthesis of unsymmetrical thiourea derivatives. Eur. Chem. Bull. 2(8), 573–575 (2013). https://doi.org/10.17628/ecb.2013.2.573-575
Yokoi, H., Addison, A.W.: Spectroscopic and redox properties of pseudotetrahedral copper (II) complexes. Their relation to copper proteins. Inorg. Chem. 16(6), 1341–1349 (1977). https://doi.org/10.1021/ic50172a018
Yousef, T.A., El-Reash, G.M.A., El-Gammal, O.A., Ahmed, S.F.: Structural, DFT and biological studies on Cu (II) complexes of semi and thiosemicarbazide ligands derived from diketo hydrazide. Polyhedron 81, 749–763 (2014). https://doi.org/10.1016/j.poly.2014.07.035
Yousef, T.A., El-Reash, G.M.A., El Morshedy, R.M.: Quantum chemical calculations, experimental investigations and DNA studies on (E)-2-((3-hydroxynaphthalen-2-yl) methylene)-N-(pyridin-2-yl) hydrazinecarbothioamide and its Mn (II), Ni (II), Cu (II), Zn (II) and Cd (II) complexes. Polyhedron 45(1), 71–85 (2012). https://doi.org/10.1016/j.poly.2012.07.041
Zaky, R.R., Yousef, T.A., Abdelghany, A.M.: Computational studies of the first order kinetic reactions for mononuclear copper (II) complexes having a hard–soft NS donor ligand. Spectrochim Acta, A 130, 178–187 (2014). https://doi.org/10.1016/j.saa.2014.02.173
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This work was supported and funded by the Deanship of Scientific Research at Imam Mohammad Ibn Saud Islamic University (IMSIU), grant number IMSIU-RG23088.
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Al-Farraj, E.S., El-Gamil, M.M. & Asla, K.A. Novel thiazole carbamothioyl benzamide derivative Mn(II), Ni(II), and Cu(II) complexes: synthesis, structural characterisation, computational, and biological potency. Opt Quant Electron 56, 72 (2024). https://doi.org/10.1007/s11082-023-05651-6
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DOI: https://doi.org/10.1007/s11082-023-05651-6