Abstract
Two imidazopyridine derivatives 6-chloro-2-(4-chlorophenyl) imidazo [1,2-a]pyridine (IPCl1) and 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbal-dehyde (IPCl2) were investigated as corrosion inhibitors of mild steel in 1.0M HCl medium using potentiodynamic polarization curves and electrochemical impedance spectroscopy. The concentrations used in this work ranged between 1.0 × 10–6 and 1.0 × 10–3 M. Those compounds were found to be good inhibitors. In addition, their adsorption on the mild steel surface obeyed the Langmuir adsorption isotherm. A quantum chemical calculation was computed using Gaussian 09 based on the density-functional theory method at B3LYP/6-31G (d, p) in order to relate some electronic properties of the studied compounds to the inhibition efficiencies achieved experimentally. The Fukui functions were calculated to estimate the most reactive sites of nucleophilic and electrophilic attacks. Finally, the molecular dynamics simulation was implemented to search for the equilibrium configurations of IPCl1 and IPCl2/Fe(110) adsorption systems in a hydrochloric acid solution at various temperatures. The theoretical and experimental results obtained were in good correlation.
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REFERENCES
Yildiz, R., An electrochemical and theoretical evaluation of 4,6-diamino-2-pyrimidinethiol as a corrosion inhibitor for mild steel in HCl solutions, Corros. Sci., 2015, vol. 90, p. 544.
Galai, M., Rbaa, M., El Kacimi, Y., Ouakki, M., et al., Anti-corrosion properties of some triphenylimidazole substituted compounds in corrosion inhibition of carbon steel in 1.0 M hydrochloric acid solution, Anal. Bioanal. Electrochem., 2017, vol. 9, no. 1, p. 80.
Shaban, S.M., Abd-Elaal, A.A., and Tawfik, S.M., Gravimetric and electrochemical evaluation of three nonionic dithiol surfactants as corrosion inhibitors for mild steel in 1 M HCl solution, J. Mol. Liq., 2016, vol. 216, p. 392.
Zarrok, H., Al-Deyab, S.S., Zarrouk, A., Salghi, R., et al., Thermodynamic characterisation and density functional theory investigation of 1,1',5,5'-tetramethyl-1H,1'H-3,3-bipyrazole as corrosion inhibitor of C38 steel corrosion in HCl, Int. J. Electrochem. Sci., 2012, vol. 7, p. 4047.
Hu, Q., Qiu, Y., Zhang, G., and Guo, X., Capsella bursa-pastoris extract as an eco-friendly inhibitor on the corrosion of Q235 carbon steels in 1 mol L−1 hydrochloric acid, Chin. J. Chem. Eng., 2015, vol. 23, p. 1408.
Hayaoui, M., Drissi, M., Fahim, M., Salim, R., et al., Benzenamine derivative as corrosion inhibitor of carbon steel in hydrochloric acid solution: electrochemical and theoretical studies, J. Mater. Environ. Sci., 2017, vol. 8, no. 5, p. 1877.
Shahabi, S., Norouzi, P., and Ganjali, M.R., Theoretical and electrochemical study of carbon steel corrosion inhibition in the presence of two synthesized Schiff base inhibitors: Application of fast Fourier transform continuous cyclic voltammetry to study the adsorption behavior, Int. J. Electrochem. Sci., 2015, vol. 10, p. 2646.
Nazeer, A.A. and Madkour, M., Potential use of smart coatings for corrosion protection of metals and alloys: a review, J. Mol. Liq., 2018, vol. 253, p. 11.
Bouoidina, A., Chaouch, M., Abdellaoui, A., Lahkimi, A., et al., Essential oil of “Foeniculum vulgare”: Antioxidant and corrosion inhibitor on mild steel immersed in hydrochloric medium, Anti-Corros. Methods Mater., 2017, vol. 64, no. 5, p. 563.
Li, G.Y., Jung, K.H., Lee, H., Son, M.K., et al., A novel imidazopyridine derivative, HS-106, induces apoptosis of breast cancer cells and represses angiogenesis by targeting the PI3K/mTOR pathway, Cancer Lett., 2013, vol. 329, p. 59.
Yun, S.M., Jung, K.H., Lee, H., Son, M.K., et al., Synergistic anticancer activity of HS-173, a novel PI3K inhibitor in combination with Sorafenib against pancreatic cancer cells, Cancer Lett., 2013, vol. 331, p. 250.
Poorfreidoni, A. and Ranjbar-Karimi, R., Synthesis of substituted imidazopyridines from perfluorinated pyridine derivatives, Tetrahedron Lett., 2016, vol. 57, p. 5781.
Liu, C., Chen, Q., Yang, M., and Schneller, S.W., C-3 halo and 3-methyl substituted 5'-nor-3-deazaaristeromycins: synthesis and antiviral properties, Bioorg. Med. Chem., 2013, vol. 21, p. 359.
Jose, G., Suresha Kumara, T.H., Nagendrappa, G., Sowmya, H.B.V., Jasinski, J.P., Millikan, S.P., Chandrika, N., More, S.S., and Harish, B.G., New polyfunctional imidazo[4,5-C]pyridine motifs: Synthesis, crystal studies, docking studies and antimicrobial evaluation, Eur. J. Med. Chem., 2014, vol. 77, p. 288.
Li, C., Chen, L., Steinhuebel, D., and Goodman, A., Rapid construction of imidazopyridines from ortho-haloaminopyridines, Tetrahedron Lett., 2016, vol. 57, p. 2708.
Grädler, U., Fuchß, T., Ulrich, W.R., Boer, R., Strub, A., Hesslinger, C., Anézo, C., Diederichs, K., and Zaliani, A., Novel nanomolar imidazo[4,5-b]pyridines as selective nitric oxide synthase (iNOS) inhibitors: SAR and structural insights, Bioorg. Med. Chem. Lett., 2011, vol. 21, no. 14, p. 4228.
Domingues, M., Casaril, A.M., Birmann, P.T., Lourenco, D.A., et al., Selanylimidazopyridine prevents lipopolysaccharide-induced depressive-like behavior in mice by targeting neurotrophins and inflammatory/oxidative mediators, Front. Neurosci., 2018, vol. 12, p. 486.
Devi, N., Jana, A.K., and Singh, V., Assessment of novel pyrazolopyridinone fused imidazopyridines as potential antimicrobial agents, Karbala Int. J. Mod. Sci., 2018, vol. 4, no. 1, p. 164.
Ghazoui, A., Saddik, R., Hammouti, B., Zarrouk, A., et al., Inhibitive effect of imidazopyridine derivative towards corrosion of C38 steel in hydrochloric acid solution, Res. Chem. Intermed., 2013, vol. 39, p. 2369.
Salghi, R., Anejjar, A., Benali, O., Al-Deyab, S.S., et al., Inhibition effect of 3-bromo-2-phenylimidazol[1,2-α]pyridine towards C38 steel corrosion in 0.5 M H2SO4 solution, Int. J. Electrochem. Sci., 2014, vol. 9, p. 3087.
Yadav, M., Behera, D., and Kumar, S., Experimental and theoretical investigation on adsorption and corrosion inhibition properties of imidazopyridine derivatives on mild steel in hydrochloric acid solution, Surf. Interface Anal., 2014, vol. 46, no. 9, p. 640.
Salim, R., Elaatiaoui, A., Benchat, N., Ech-chihbi, E., et al., Corrosion behavior of a smart inhibitor in hydrochloric acid molar: experimental and theoretical studies, J. Mater. Environ. Sci., 2017, vol. 8, no. 10, p. 3747.
Salim, R., Ech-chihbi, E., Oudda, H., El Hajjaji, F., Taleb, M., and Jodeh, S., A review on the assessment of imidazo[1,2-α]pyridines as corrosion inhibitor of metals, J. Bio- Tribo-Corros., 2019, vol. 5, p. 14. https://doi.org/10.1007/s40735-018-0207-3
Nahle, A., El-Hajjaji, F., Ghazoui, A., Benchat, N., Taleb, M., Saddik, R., Elaatiaoui, A., Koudad, M., and Hammouti, B., Effect of substituted methyl group by phenyl group in pyridazine ring on the corrosion inhibition of mild steel in 1.0 M HCl, Anti-Corros. Methods Mater., 2018, vol. 65, no. 1, p. 87.
Zarrouk, A., Zarrok, H., Ramli, Y., Bouachrine, M., et al., Inhibitive properties, adsorption and theoretical study of 3,7-dimethyl-1-(prop-2-yn-1-yl)quinoxalin-2(1H)-one as efficient corrosion inhibitor for carbon steel in hydrochloric acid solution, J. Mol. Liq., 2016, vol. 222, p. 239.
Zarrouk, A., Hammouti, B., Dafali, A., Bouachrine, M., et al., A theoretical study on the inhibition efficiencies of some quinoxalines as corrosion inhibitors of copper in nitric acid, J. Saudi Chem. Soc., 2014, vol. 18, p. 450.
El Faydy, M., Touir, R., Ebn Touhami, M., Zarrouk, A., et al., Corrosion inhibition performance of newly synthesized 5-alkoxymethyl-8-hydroxyquinoline derivatives for carbon steel in 1 M HCl solution: Experimental, DFT and Monte Carlo simulation studies, Phys. Chem. Chem. Phys., 2018, vol. 20, no. 30, p. 20167.
Singh, A., Ansari, K.R., Kumar, A., Liu, W., et al., Electrochemical, surface and quantum chemical studies of novel imidazole derivatives as corrosion inhibitors for J55 steel in sweet corrosive environment, J. Alloys Compd., 2017, vol. 712, p. 121.
Alaoui, K., Touir, R., Galai, M., Serrar, H., et al., Electrochemical and computational studies of some triazepine carboxylate compounds as acid corrosion inhibitors for mild steel, J. Bio- Tribo-Corros., 2018, vol. 4, p. 37.
Materials Studio, Revision 8.0, San Diego: Accelrys, 2016.
Khaled, K.F. and Amin, M.A., Corrosion monitoring of mild steel in sulphuric acid solutions in presence of some thiazole derivatives—Molecular dynamics, chemical and electrochemical studies, Corros. Sci., 2009, vol. 51, p. 1964.
Rbaa, M., Benhiba, F., Obot, I.B., Oudda, H., et al., Two new 8-hydroxyquinoline derivatives as an efficient corrosion inhibitors for mild steel in hydrochloric acid: synthesis, electrochemical, surface morphological, UV-visible and theoretical studies, J. Mol. Liq., 2019, vol. 276, p. 120.
Sun, H., COMPASS: An ab initio force-field optimized for condensed-phase applications—Overview with details on alkane and benzene compounds, J. Phys. Chem. B, 1998, vol. 102, p. 7338.
Saha, S.K., Ghosh, P., Hens, A., Murmu, N.C., et al., Density functional theory and molecular dynamics simulation study on corrosion inhibition performance of mild steel by mercapto-quinoline Schiff base corrosion inhibitor, Phys. E (Amsterdam), 2015, vol. 66, p. 332.
Ech-chihbi, E., Belghiti, M.E., Salim, R., Oudda, H., et al., Experimental and computational studies on the inhibition performance of the organic compound “2-phenylimidazo [1,2-a]pyrimidine-3-carbaldehyde” against the corrosion of carbon steel in 1.0 M HCl solution, Surf. Interfaces, 2017, vol. 9, p. 206.
Markhali B.P., Naderi R., Mahdavian M., Sayebani M., et al., Electrochemical impedance spectroscopy and electrochemical noise measurements as tools to evaluate corrosion inhibition of azole compounds on stainless steel in acidic media, Corros. Sci., 2013, vol. 75, p. 269.
Khattabi, M., Benhiba, F., Tabti, S., Djedouani, A., et al., Performance and computational studies of two soluble pyran derivatives as corrosion inhibitors for mild steel in HCl, J. Mol. Struct., 2018, vol. 1196, p. 231.
El-Hajjaji, F., Messali, F.M., Aljuhani, A., Aouad, M.R., Hammouti, B., Belghiti, M.E., Chauhan, D.S., and Quraishi, M.A., Pyridazinium-based ionic liquids as novel and green corrosion inhibitors of carbon steel in acid medium: Electrochemical and molecular dynamics simulation studies, J. Mol. Liq., 2018, vol. 249, p. 997.
Ribeiro, D.V., and Abrantes, J.C.C., Application of electrochemical impedance spectroscopy (EIS) to monitor the corrosion of reinforced concrete: A new approach, Constr. Build. Mater., 2016, vol. 111, p. 98.
Haruna, K., Saleh, T.A., Obot, I.B., and Umoren, S.A., Cyclodextrin-based functionalized graphene oxide as an effective corrosion inhibitor for carbon steel in acidic environment, Prog. Org. Coat., 2019, vol. 128, p. 157.
Galai, M., El Faydy, M., El Kacimi, Y., Dahmani, K., et al., Synthesis, characterization and anti-corrosion properties of novel quinolinol on C-steel in a molar hydrochloric acid solution, Port. Electrochim. Acta, 2017, vol. 35, no. 4, p. 233.
Verma, C., Quraishi, M.A., Obot, I.B., and Ebenso, E.E., Effect of substituent dependent molecular structure on anti-corrosive behavior of one-pot multicomponent synthesized pyrimido [2,1-B] benzothiazoles: Computer modeling supported experimental studies, J. Mol. Liq., 2019, vol. 287, p. 110972.
Hamani, H., Douadi, T., Al-Noaimi, M., Issaadi, S., et al., Electrochemical and quantum chemical studies of some azomethine compounds as corrosion inhibitors for mild steel in 1 M hydrochloric acid, Corros. Sci., 2014, vol. 88, p. 234.
Wang, C., Chen, J., Han, J., Wang, C., and Hu, B., Enhanced corrosion inhibition performance of novel modified polyaspartic acid on carbon steel in HCl solution, J. Alloys Compd., 2019, vol. 771, p. 736.
Verma, C., Quraishi, M.A., and Singh, A., 5-Substituted 1H-tetrazoles as effective corrosion inhibitors for mild steel in 1 M hydrochloric acid, J. Taibah Univ. Sci., 2016, vol. 10, p. 718.
El Faydy, M., Galai, M., El Assyry, A., Tazouti, A., et al., Experimental investigation on the corrosion inhibition of carbon steel by 5-(chloromethyl)-8-quinolinol hydrochloride in hydrochloric acid solution, J. Mol. Liq., 2016, vol. 219, p. 396.
Tayebi, H., Bourazmi, H., Himmi, B., El Assyry, A., et al., An electrochemical and theoretical evaluation of new quinoline derivative as a corrosion inhibitor for carbon steel in HCl solutions, Pharm. Lett., 2014, vol. 6, no. 6, p. 20.
Ozdemir, C.S. and Onal, Y., Study to observe the applicability of the adsorption isotherms used for the adsorption of medicine organics onto activated carbon, Part. Sci. Technol., 2016, vol. 36, no. 2, p. 254.
Rahiman, A.F.S.A. and Sethumanickam, S., Corrosion inhibition, adsorption and thermodynamic properties of poly (vinyl alcohol-cysteine) in molar HCl, Arab. J. Chem., 2017, vol. 10, p. 53358.
El-Hajjaji, F., Messali, M., Martínez de Yuso, M.V., Rodríguez-Castellón, E., Almutairi, S., Bandosz Teresa, J., and Algarra, M., Effect of 1-(3-phenoxypropyl) pyridazin-1-ium bromide on steel corrosion inhibition in acidic medium, J. Colloid Interface Sci., 2019, vol. 541, p. 418.
Ismaily, A.K., Ouazzani, F., Kandrirodi, Y., Azaroual, A.M., et al., Effect of some benzimidazolone compounds on C38 steel corrosion in hydrochloric acid solution, J. Mater. Environ. Sci., 2016, vol. 7, no. 1, p. 244.
Deyab, M.A. and Abd El-Rehim, S.S., Influence of polyethylene glycols on the corrosion inhibition of carbon steel in butyric acid solution: weight loss, EIS and theoretical studies, Int. J. Electrochem. Sci., 2013, vol. 8, no. 12, p. 12613.
El Hajjaji, F., Abrigach, F., Hamed, O., Hasan, A.R., et al., Corrosion resistance of mild steel coated with organic material containing pyrazol moiety, Coatings, 2018, vol. 8, no. 10, p. 330.
ElBelghiti, M., Karzazi, Y., Dafali, A., Hammouti, B., et al., Experimental, quantum chemical and Monte Carlo simulation studies of 3,5-disubstituted-4-amino-1,2,4-triazoles as corrosion inhibitors on mild steel in acidic medium, J. Mol. Liq., 2016, vol. 218, p. 281.
Ouakki, M., Rbaa, M., Galai, M., Lakhrissi, B., Rifi, E.H., and Cherkaoui, M., Experimental and quantum chemical investigation of imidazole derivatives as corrosion inhibitors on mild steel in 1.0 M hydrochloric acid, J. Bio- Tribo-Corros., 2018, vol. 4, p. 35.
Ech-chihbi, E., Nahle, N., Salim, R., Oudda, H., et al., An investigation into quantum chemistry and experimental evaluation of imidazopyridine derivatives as corrosion inhibitors for C-steel in acidic media, J. Bio- Tribo-Corros., 2019, vol. 5, p. 24.
Saady, A., El-Hajjaji, F., Taleb, M., Ismaily Alaoui, K., et al., Experimental and theoretical tools for corrosion inhibition study of mild steel in aqueous hydrochloric acid solution by new Indanones derivatives, Mater. Discovery, 2019, vol. 12, p. 30.
Bedair, M.A., The effect of structure parameters on the corrosion inhibition effect of some heterocyclic nitrogen organic compounds, J. Mol. Liq., 2016, vol. 219, p. 128.
Armakovic, S., Armakovic, S.J., Vranes, M., Tot, A., and Gadzuric, S., Determination of reactive properties of 1-butyl-3-methylimidazolium taurate ionic liquid employing DFT calculations, J. Mol. Liq., 2016, vol. 222, p. 796.
van Gunsteren, W.F. and Berendsen, H.J.C., Computer simulation of molecular dynamics: Methodology, applications, and perspectives in chemistry, Angew. Chem., Int. Ed., 1990, vol. 29, p. 992.
Hsissou, R., Dagdag, O., About, S., Benhiba, F., et al., Novel derivative epoxy resin TGETET as a corrosion inhibition of E24 carbon steel in 1.0 M HCl solution. Experimental and computational (DFT and MD simulations) methods, J. Mol. Liq., 2019, vol. 284, p. 182.
Rouifi, Z., Benhiba, F., El Faydy, M., Laabaissi, T., et al., Performance and computational studies of new soluble triazole as corrosion inhibitor for carbon steel in HCl, Chem. Data Collect., 2019, vol. 22, p. 100242.
Tang, Y., Yang, X., Yang, W., Chen, Y., et al., Experimental and molecular dynamics studies on corrosion inhibition of mild steel by 2-amino-5-phenyl-1,3,4-thiadiazole, Corros. Sci., 2010, vol. 52, p. 242.
Obot, I., Obi-Egbedi, N., Ebenso, E.E., Afolabi, A., et al., Experimental, quantum chemical calculations, and molecular dynamic simulations insight into the corrosion inhibition properties of 2-(6-methylpyridin-2-yl)oxazolo [5,4-f][1,10]phenanthroline on mild steel, Res. Chem. Intermed., 2013, vol. 39, p. 1927.
Kaya, S., Guo, L., Kaya, C., Tuzun, B., Obot, I.B., Touir, R., and Islam, N., Quantum chemical and molecular dynamic simulation studies for the prediction of inhibition efficiencies of some piperidine derivatives on the corrosion of iron, J. Taiwan Inst. Chem. Eng., 2016, vol. 65, p. 522.
Salarvand, Z., Amirnasr, M., Talebian, M., Raeissi, K., et al., Enhanced corrosion resistance of mild steel in 1 M HCl solution by trace amount of 2-phenyl-benzothiazole derivatives: experimental, quantum chemical calculations and molecular dynamics (MD) simulation studies, Corros. Sci., 2017, vol. 114, p. 133.
Kokalj, A., Comments on the “Reply to comments on the paper ‘On the nature of inhibition performance of imidazole on iron surface’” by J.O. Mendes and A.B. Rocha, Corros. Sci., 2013, vol. 70, p. 294.
Liu, A., Ren, X., Zhang, J., Wang, C., et al., Theoretical and experimental studies of the corrosion inhibition effect of nitrotetrazolium blue chloride on copper in 0.1 M H2SO4, RSC Adv., 2014, vol. 4, p. 40606.
Zhang, D., Tang, Y., Qi, S., Dong, D., et al., The inhibition performance of long-chain alkyl-substituted benzimidazole derivatives for corrosion of mild steel in HCl, Corros. Sci., 2016, vol. 102, p. 517.
Naeiji, P., Varaminian, F., and Rahmati, M., Comparison of the thermodynamic, structural and dynamical properties of methane/water and methane/water/hydrate systems using molecular dynamic simulations, J. Nat. Gas Sci. Eng., 2017, vol. 44, p. 122.
Bhaskar, V., Chowdary, R., Dixit, S.R., and Joshi, S.D., Synthesis, molecular modeling and BACE-1 inhibitory study of tetrahydrobenzo[b]pyran derivatives, Bioorg. Chem., 2019, vol. 84, p. 202.
Xie, S.W., Liu, Z., Han, G.C., Li, W., et al., Molecular dynamics simulation of inhibition mechanism of 3,5-dibromo salicylaldehyde Schiff’s base, Comput. Theor. Chem., 2015, vol. 1063, p. 50.
Guo, A., Duan, G., He, K., Sun, B., et al., Synergistic effect between 2-oleyl-1-oleylamidoethyl imidazoline ammonium methylsulfate and halide ion by molecular dynamics simulation, Comput. Theor. Chem., 2013, vol. 1015, p. 21.
El Faydy, M., Benhiba, F., Lakhrissi, B., Ebn Touhami, M., et al., The inhibitive impact of both kinds of 5-isothiocyanatomethyl-8-hydroxyquinoline derivatives on the corrosion of carbon steel in acidic electrolyte, J. Mol. Liq., 2019, vol. 295, p. 111629.
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Salim, R., Nahlé, A., El-Hajjaji, F. et al. Experimental, Density Functional Theory, and Dynamic Molecular Studies of Imidazopyridine Derivatives as Corrosion Inhibitors for Mild Steel in Hydrochloric Acid. Surf. Engin. Appl.Electrochem. 57, 233–254 (2021). https://doi.org/10.3103/S1068375521020083
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DOI: https://doi.org/10.3103/S1068375521020083