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Novel 1,3,4-Thiadiazolethiosemicarbazones Derivatives and Their Divalent Cobalt-Complexes: Synthesis, Characterization and Their Efficiencies for Acidic Corrosion Inhibition of Carbon Steel

  • Tahani M. Bawazeer
  • Hoda A. El-GhamryEmail author
  • Thoraya A. Farghaly
  • Ahmed Fawzy
Article

Abstract

Two newly synthesized ligands based on 1,3,4-thiadiazolethiosemicarbazone have been isolated by the condensation reaction of 2,3-disubstituted-5-acetyl-1,3,4-thiadiazole derivatives with thiosemicarbazide in acidic medium in addition to their Co(II) chelates. The synthesized cobalt chelates that have been obtained by the reaction of each ligand with cobalt acetate were confirmed to have the formulae [(LM)Co(OAc)(H2O)2]H2O (LM–Co) and [(LN)Co(OAc)(H2O)2]0.5CH3OH (LN–Co); where LM and LN are 1,3,4-thiadiazolethiosemicarbazone ligands with methyl and nitro substituents, respectively. Comparison of the IR spectrum of each ligand with that of its cobalt complex implied that both ligands acted as monobasic tridentate connecting to the cobalt ion through N atoms of both azomethine group and thiadiazole ring and S atom of deprotonated SH group as well. The two complexes have been proved to have octahedral geometrical structures. The synthesized compounds were studied as corrosion inhibitors for carbon steel in molar hydrochloric acid solution using several chemical and electrochemical techniques. The investigational outcomes displayed that the inhibition efficiencies of the examined compounds were found to augment as the concentrations of such compounds raised. At comparable inhibitors concentration, the inhibition efficiency was a little increased following the order: LM > LM–Co > LN > LN–Co. The acquired high inhibition efficiencies of the explored compounds were ascribed to the potent adsorption of the molecules on the steel surface and construction of adherent layers. Such adsorption was found to accord with Langmuir adsorption isotherm. There is a good correlation in the results obtained from the different measurements used.

Keywords

Thiadiazoles Thiosemicarbazone Cobalt chelates Acidic corrosion Inhibition 

Notes

References

  1. 1.
    D. Karcz, A. Matwijczuk, B. Boron, B. Creaven, L. Fiedor, A. Niewiadomy, M. Gagos, Isolation and spectroscopic characterization of Zn(II), Cu(II), and Pd(II) complexes of 1,3,4-thiadiazole-derived ligand. J. Mol. Struct. 1128, 44–50 (2017)CrossRefGoogle Scholar
  2. 2.
    L.M.T. Frija, A.J.L. Pombeiro, M.N. Kopylovich, Coordination chemistry of thiazoles, isothiazoles and thiadiazoles. Coord. Chem. Rev. 308, 32–55 (2016)CrossRefGoogle Scholar
  3. 3.
    K. Zhang, H. Zheng, C. Hua, M. Xin, J. Gao, Y. Li, Novel fluorescent N,O-chelated fluorine-boron benzamide complexes containing thiadiazoles: synthesis and fluorescence characteristics. Tetrahedron 74, 4161–4167 (2018)CrossRefGoogle Scholar
  4. 4.
    C. Richardson, P.J. Steel, D.M. D’Alessandro, P.C. Junk, F.R. Keene, Mono- and di-nuclear complexes of the ligands 3,4-di(2-pyridyl)-1,2,5-oxadiazole and 3,4-di(2-pyridyl)-1,2,5-thiadiazole; new bridges allowing unusually strong metal–metal interactions. J. Chem. Soc. Dalton Trans. (2002).  https://doi.org/10.1039/B202954E Google Scholar
  5. 5.
    G.-L. Wen, Y.-Y. Wang, P. Liu, C.-Y. Guo, W.-H. Zhang, Q.-Z. Shi, A series of 1-D to 3-D metal–organic coordination architectures assembled with V-shaped bis(pyridyl)thiadiazole under co-ligand intervention. Inorg. Chim. Acta 362, 1730–1738 (2009)CrossRefGoogle Scholar
  6. 6.
    B. Ardan, Y. Slyvka, E. Goreshnik, M. Myskiv, First N-allyl-aminothiadiazole copper(i) π-complexes: synthesis and structural peculiarities of Cu(L)CF3SO3] and [Cu2(L)2(H2O)2](SiF6) · 2.5H2O compounds (L = 2-(allyl)-amino-5-methyl-1,3,4-thiadiazole). Acta Chim. Slov. 60, 484–490 (2013)Google Scholar
  7. 7.
    S. Chandra, S. Gautam, A. Kumar, M. Madan, Coordination mode of pentadentate ligand derivative of 5-amino-1,3,4-thiadiazole-2-thiol with nickel(II) and copper(II) metal ions: synthesis, spectroscopic characterization, molecular modeling and fungicidal study. Spectrochim. Acta A 136, 672–681 (2015)CrossRefGoogle Scholar
  8. 8.
    A. Smaili, L.A. Rifai, S. Esserti, T. Koussa, F. Bentiss, S. Guesmi, A. Laachir, M. Faize, Copper complexes of the 1,3,4-thiadiazole derivatives modulate antioxidant defense responses and resistance in tomato plants against fungal and bacterial diseases. Pestic. Biochem. Physiol. 143, 26–32 (2017)CrossRefGoogle Scholar
  9. 9.
    H. Zine, L.A. Rifai, T. Koussa, F. Bentiss, S. Guesmi, A. Laachir, K. Makroum, M. Belfaiza, M. Faize, The mononuclear nickel (II) complex bis(azido-kN)bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ2N2, N3]nickel(II) protects tomato from Verticillium dahliae by inhibiting the fungal growth and activating plant defenses. Pest Manag. Sci. 73, 188–197 (2017)CrossRefGoogle Scholar
  10. 10.
    M. El Azhar, B. Mernari, M. Traisnel, F. Bentiss, M. Lagrenée, Corrosion inhibition of mild steel by the new class of inhibitors [2,5-bis(n-pyridyl)-1,3,4-thiadiazoles] in acidic media. Corrosion sci. 43, 2229–2238 (2001)CrossRefGoogle Scholar
  11. 11.
    F. Bentiss, M. Lebrini, H. Vezin, M. Lagrené, Experimental and theoretical study of 3-pyridyl-substituted 1,2,4-thiadiazole and 1,3,4-thiadiazole as corrosion inhibitors of mild steel in acidic media. Mater. Chem. Phys. 87, 18–23 (2004)CrossRefGoogle Scholar
  12. 12.
    F. Bentiss, M. Traisnel, M. Lagrenee, Influence of 2,5-bis(4-dimethylaminophenyl)-1,3,4-thiadiazole on corrosion inhibition of mild steel in acidic media. J. Appl. Electrochem. 31, 41–48 (2001)CrossRefGoogle Scholar
  13. 13.
    M.A. Arenos, M. Bethencourt, F.G. Botana, J. Domborenena, M. Marcos, Inhibition of 5083 aluminium alloy and galvanised steel by lanthanide salts. Corros. Sci. 43, 157–170 (2001)CrossRefGoogle Scholar
  14. 14.
    D. Gustincic, A. Kokalj, DFT study of azole corrosion inhibitors on Cu2O model of oxidized copper surfaces: I. Molecule–surface and Cl–surface bonding. Metals 8, 311–338 (2018)CrossRefGoogle Scholar
  15. 15.
    I.A. Arkhipushkin, K.S. Shikhaliev, A.Y. Potapov, L.V. Sapronova, L.P. Kazansky, Inhibition of brass (80/20) by 5-mercaptopentyl-3-amino-1,2,4-triazole in neutral solutions. Metals 7, 488–500 (2017)CrossRefGoogle Scholar
  16. 16.
    A. Fawzy, M. Abdallah, I.A. Zaafarany, S.A. Ahmed, I.I. Althagafi, Thermodynamic, kinetic and mechanistic approach to the corrosion inhibition of carbon steel by new synthesized amino acids-based surfactants as green inhibitors in neutral and alkaline aqueous media. J. Mol. Liq. 265, 276–291 (2018)CrossRefGoogle Scholar
  17. 17.
    A. Fawzy, I.A. Zaafarany, H.M. Ali, M. Abdallah, Corrosion inhibition performance of a novel cationic surfactant for protection of carbon steel pipeline in acidic media. Int. J. Electrochem. Sci. 13, 4575–6842 (2018)CrossRefGoogle Scholar
  18. 18.
    R.F. Godec, M.G. Pavlovic, Synergistic effect between non-ionic surfactant and halide ions in the forms of inorganic or organic salts for the corrosion inhibition of stainless-steel X4Cr13 in sulphuric acid. Corros. Sci. 58, 192–201 (2012)CrossRefGoogle Scholar
  19. 19.
    E. Khamis, M.A. Ameer, N.M. AlAndis, G. Al-Senani, Effect of thiosemicarbazones on corrosion of steel in phosphoric acid produced by wet process. Corrosion 56, 127–138 (2000)CrossRefGoogle Scholar
  20. 20.
    N. Karakus, K. Sayin, The investigation of corrosion inhibition efficiency on some benzaldehyde thiosemicarbazones and their thiole tautomers: computational study. J. Taiwan Inst. Chem. E. 48, 95–102 (2015)CrossRefGoogle Scholar
  21. 21.
    C. Verma, L.O. Olasunkanmi, E.E. Ebenso, M.A. Quraishi, Substituents effect on corrosion inhibition performance of organic compounds in aggressive ionic solutions: a review. J. Mol. Liq. 251, 100–118 (2018)CrossRefGoogle Scholar
  22. 22.
    M. Yadav, S. Kumar, I. Bahadur, D. Ramjugernath, Electrochemical and quantum chemical studies on synthesized phenylazopyrimidone dyes as corrosion inhibitors for mild steel in a 15% HCl solution. Int. J. Electrochem. Sci. 9, 3928–3950 (2014)Google Scholar
  23. 23.
    M.A. Hegazy, H.M. Ahmed, A.S. El-Tabei, Investigation of the inhibitive effect of p-substituted 4-(N,N,N-dimethyldodecylammonium bromide)benzylidene-benzene-2-yl-amine on corrosion of carbon steel pipelines in acidic medium. Corros. Sci. 53, 671–678 (2011)CrossRefGoogle Scholar
  24. 24.
    S.K. Saha, A. Dutta, P. Ghosh, D. Sukul, P. Banerjee, Novel Schiff-base molecules as efficient corrosion inhibitors for mild steel surface in 1 M HCl medium: experimental and theoretical approach. Phys. Chem. Chem. Phys. 18, 17898–17911 (2016)CrossRefGoogle Scholar
  25. 25.
    N.F. Eweiss, A.O. Osman, Synthesis of heterocycles. Part II. New routes to acetylthiadiazolines and alkylazothiazoles. J. Heterocycl. Chem. 17, 1713–1717 (1980)CrossRefGoogle Scholar
  26. 26.
    W.J. Geary, The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord. Chem. Rev. 7, 81–122 (1971)CrossRefGoogle Scholar
  27. 27.
    H. El-Ghamry, N. El-Wakiel, A. Khamis, Synthesis, structure, antiproliferative activity and molecular docking of divalent and trivalent metal complexes of 4H‐3,5‐diamino‐1,2,4‐triazole and α‐hydroxynaphthaldehyde Schiff base ligand. Appl. Organomet. Chem. 32, e4583 (2018)CrossRefGoogle Scholar
  28. 28.
    M.M. Alsharekh, I.I. Althagafi, M.R. Shaaban, T.A. Farghaly, Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities. Res. Chem. Intermed. 45, 127–154 (2019)CrossRefGoogle Scholar
  29. 29.
    H.A. El-Ghamry, M. Gaber, T.A. Farghaly, Synthesis, structural characterization, molecular modeling and DNA binding ability of CoII, NiII, CuII, ZnII, PdII and CdII complexes of benzocycloheptenone thiosemicarbazone ligand. Mini. Rev. Med. Chem. 19, 1068–1079 (2019)CrossRefGoogle Scholar
  30. 30.
    H.A. El-Ghamry, K. Sakai, S. Masaoka, K. El-Baradie, R. Issa, Synthesis and characterization of self-assembled coordination polymers of N-diaminomethylene-4-(3-formyl-4-hydroxy-phenylazo)-benzenesulfonamide. J. Coord. Chem. 65, 780–794 (2012)CrossRefGoogle Scholar
  31. 31.
    P.F. Rapheal, E. Manoj, M.R. PrathapachandraKurup, Copper(II) complexes of N(4)-substituted thiosemicarbazones derived from pyridine-2-carbaldehyde: crystal structure of a binuclear complex. Polyhedron 26, 818–828 (2007)CrossRefGoogle Scholar
  32. 32.
    K. Nakamoto (ed.), Infrared spectra of inorganic and coordination compounds (Wiley, New York, 1986)Google Scholar
  33. 33.
    D.-D. Yang, R. Wang, J.-L. Zhu, Q.-Y. Cao, J. Qin, H.-L. Zhu, Synthesis, crystal structures, molecular docking, in vitro monoamine oxidase-B inhibitory activity of transition metal complexes with 2-{4-[bis (4-fluorophenyl)methyl]piperazin-1-yl} acetic acid. J. Mol. Struct. 1128, 493–498 (2017)CrossRefGoogle Scholar
  34. 34.
    A.M. Gouda, H.A. El-Ghamry, T.M. Bawazeer, T.A. Farghaly, A.N. Abdalla, A. Aslam, Antitumor activity of pyrrolizines and their Cu(II) complexes: design, synthesis and cytotoxic screening with potential apoptosis-inducing activity. Eur. J. Med. Chem. 145, 350–359 (2018)CrossRefGoogle Scholar
  35. 35.
    M. Shakir, A. Abbasi, M. Azam, A.U. Khan, Synthesis, spectroscopic studies and crystal structure of the Schiff base ligand L derived from condensation of 2-thiophenecarboxaldehyde and 3,3′-diaminobenzidine and its complexes with Co(II), Ni(II), Cu(II), Cd(II) and Hg(II): comparative DNA binding studies of L and its Co(II), Ni(II) and Cu(II) complexes. Spectrochim. Acta A 79, 1866–1875 (2011)CrossRefGoogle Scholar
  36. 36.
    N.H. Yarkandi, H.A. El-Ghamry, M. Gaber, Synthesis, spectroscopic and DNA binding ability of CoII, NiII, CuII and ZnII complexes of Schiff base ligand (E)-1-(((1H-benzo[d]imidazol-2-yl)methylimino)methyl)naphthalen-2-ol. X-ray crystal structure determination of cobalt (II) complex. Mater. Sci. Eng., C 75, 1059–1067 (2017)CrossRefGoogle Scholar
  37. 37.
    A.B.P. Lever, Inorganic electronic spectroscopy, 2nd edn. (Elsevier, Amsterdam, 1984)Google Scholar
  38. 38.
    M. Pfaller, L. Burmeister, M.A. Bartlett, M.G. Rinaldi, Multicenter evaluation of four methods of yeast inoculum preparation. J. Clin. Microbiol. 26, 1437–1441 (1988)Google Scholar
  39. 39.
    L.B. Tang, G.N. Mu, G.H. Liu, The effect of neutral red on the corrosion inhibition of cold rolled steel in 1.0 M hydrochloric acid. Corros. Sci. 45, 2251–2262 (2003)CrossRefGoogle Scholar
  40. 40.
    P. Manjula, S. Manonmani, P. Jayaram, S. Rajendran, Corrosion behaviour of carbon steel in the presence of N-cetyl-N,N,N-trimethylammonium bromide, Zn2+ and calcium gluconate. Anti-Corros. Methods Mater. 48, 319–324 (2001)CrossRefGoogle Scholar
  41. 41.
    H. Ma, S. Chen, L. Niu, S. Zhao, S. Li, D. Li, Inhibition of copper corrosion by several Schiff bases in aerated halide solutions. J. Appl. Electrochem. 32, 65–72 (2002)CrossRefGoogle Scholar
  42. 42.
    M. Abdallah, H.M. Altass, B.A. Al Jahdaly, M.M. Salem, Some natural aqueous extracts of plants as green inhibitor for dissolution of carbon steel in 0.5 M sulfuric acid. Green Chem. Lett. Rev. 11, 189–196 (2018)CrossRefGoogle Scholar
  43. 43.
    M. Christov, A. Popova, Adsorption characteristics of corrosion inhibitors from corrosion rate measurements. Corros. Sci. 46, 1613–1620 (2004)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Tahani M. Bawazeer
    • 1
    • 2
  • Hoda A. El-Ghamry
    • 1
    • 3
    Email author
  • Thoraya A. Farghaly
    • 4
  • Ahmed Fawzy
    • 1
    • 5
  1. 1.Chemistry Department, Faculty of Applied ScienceUmm Al-Qura UniversityMakkahSaudi Arabia
  2. 2.Medical Applications of Nanobiotechnology Research Group, King Fahad Medical Research CenterKing Abdulaziz UniversityJeddahSaudi Arabia
  3. 3.Chemistry Department, Faculty of ScienceTanta UniversityTantaEgypt
  4. 4.Chemistry Department, Faculty of ScienceCairo UniversityGizaEgypt
  5. 5.Chemistry Department, Faculty of ScienceAssiut UniversityAssiutEgypt

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