A theoretical approach to the inhibitive effect of two new Schiff base compounds

Year 2022, Volume: 64 Issue: 1, 1 - 19, 18.07.2022

Burçin Çakır Kaan Cebesoy Emregül

Abstract

The corrosion inhibition of mild steel was investigated using theoretical calculations in 2,2-[2,2-{2-hidroxy propane-1,3diyl}bis(oxy)bis(2,1-phenylene)]bis(methane-l-yl-l-ylidene ) bis(azan-l-yl-l-ylidene)diphenol (DF1) and 2,2-[2,2-{ethane-1,2diylbis(oxy)}bis(2,1-phenylene)]bis(methane-l-yl-l-ylidene)bis(azan-l-yl-l-yl-idene) diphenol (DF2). Various quantum chemical descriptors like E_HOMO, E_LUMO, ΔE, chemical hardness were calculated and discussed.

Keywords

Quantum chemical calculations, DFT, electrochemical impedance spectroscopy (EIS), mild steel, adsorption

Project Number

15B0430001

References

• [1] Natarajan, K.A., K. A. Natarajan, Advances in Corrosion Engineering, Lecture 1, IISc Bangalore, 2017.
• [2] Fouda, A.S., Hassan, A.F., Elmorsi, M.A., Fayed, T.A., Abdelhakim, A., Chalcones as environmentally-friendly corrosion inhibitors for stainless steel type 304 in 1 M HCl solutions, International Journal of Electrochemical Science, 9 (2014), 1298 - 1320.
• [3] Verma, C.B., Reddy, M.J., Quraishi, M.A., Ultrasound assisted green synthesis of 3-(4-(Dimethylamino) Phenyl)-1-Phenylprop-2-En-1-One and its heterocyclics derived from Hydrazine, Urea and Thiourea as Corrosion Inhibitor for mild steel in 1M HCl, Analytical and Bioanalytical Electrochemistry, 6 (5) (2014), 515-534.
• [4] Subasri, R., Shinohara, T., Mori, K., Modified TiO2 coatings for cathodic protection applications, in: Science and Technology of Advanced Materials, 6 (2005),501-507. https://doi.org/10.1016/j.stam.2005.01.003. [5] Kim, D.K., Muralidharan, S., Ha, T.H., Bae, J.H., Ha, Y.C., Lee, H.G., Scantlebury, J.D., Electrochemical studies on the alternating current corrosion of mild steel under cathodic protection condition in marine environments, Electrochimica Acta, 51 (25) (2006), 5259-5267. https://doi.org/10.1016/j.electacta.2006.01.054.
• [6] Cecchetto, L., Delabouglise, D., Petit, J.P., On the mechanism of the anodic protection of aluminium alloy AA5182 by emeraldine base coatings. Evidences of a galvanic coupling, Electrochimica Acta, 52 (11) (2007), 3485-3492. https://doi.org/10.1016/j.electacta.2006.10.009.
• [7] Praveen, B.M., Venkatesha, T. V., Arthoba Naik, Y., Prashantha, K., Corrosion studies of carbon nanotubes-Zn composite coating, Surface and Coatings Technology, 201 (12) (2007),5836-5842. https://doi.org/10.1016/j.surfcoat.2006.10.034.
• [8] Zhang, F., Tang, Y., Cao, Z., Jing, W., Wu, Z., Chen, Y., Performance and theoretical study on corrosion inhibition of 2-(4-pyridyl)-benzimidazole for mild steel in hydrochloric acid, Corrosion Science, 61 (2012), 1-9. https://doi.org/10.1016/j.corsci.2012.03.045.
• [9] Dohare, P., Quraishi, M.A., Obot, I.B., A combined electrochemical and theoretical study of pyridine-based Schiff bases as novel corrosion inhibitors for mild steel in hydrochloric acid medium, Journal of Chemical Sciences, 130 (1) (2018), 1–19. https://doi.org/10.1007/s12039-017-1408-x.
• [10] Da Silva, C.M., Da Silva, D.L., Modolo, L. V., Alves, R.B., De Resende, M.A., Martins, C.V.B., De Fátima, Â., Schiff bases: A short review of their antimicrobial activities, Journal of Advanced Research, 2 (1) (2011), 1-8. https://doi.org/10.1016/j.jare.2010.05.004.
• [11] Silku, P., Özkinali, S., Öztürk, Z., Asan, A., Köse, D.A., Synthesis of novel Schiff Bases containing acryloyl moiety and the investigation of spectroscopic and electrochemical properties, Journal of Molecular Structure, 1116 (2016), 72-83. https://doi.org/10.1016/j.molstruc.2016.03.028.
• [12] Small, B.L., Brookhart, M., Bennett, A.M.A., Highly active iron and cobalt catalysts for the polymerization of ethylene, Journal of the American Chemical Society, 120 (16) (1998), 4049–4050. https://doi.org/10.1021/ja9802100.
• [13] Ulusoy, M., Birel, Ö., Ahin, O., Büyükgüngör, O., Cetinkaya, B., Structural, spectral, electrochemical and catalytic reactivity studies of a series of N 2O 2 chelated palladium(II) complexes, Polyhedron, 38 (1) (2012), 141–148. https://doi.org/10.1016/j.poly.2012.02.035.
• [14] Kumar, R., Kim, H., Singh, G., Experimental and theoretical investigations of a newly synthesized azomethine compound as inhibitor for mild steel corrosion in aggressive media: A comprehensive study, Journal of Molecular Liquids, 259 (2018), 199–208. https://doi.org/10.1016/j.molliq.2018.02.123.
• [15] Vikneshvaran, S., Velmathi, S., Adsorption of L-Tryptophan-derived chiral Schiff bases on stainless steel surface for the prevention of corrosion in acidic environment: Experimental, theoretical and surface studies, Surfaces and Interfaces, 6 (2017), 134-142. https://doi.org/10.1016/j.surfin.2017.01.001.
• [16] Gece, G., The use of quantum chemical methods in corrosion inhibitor studies, Corrosion Science, 50 (11) (2008), 2981-2992. https://doi.org/10.1016/j.corsci.2008.08.043.
• [17] Guo, L., Kaya, S., Obot, I.B., Zheng, X., Qiang, Y., Toward understanding the anticorrosive mechanism of some thiourea derivatives for carbon steel corrosion: A combined DFT and molecular dynamics investigation, Journal of Colloid and Interface Science, 506 (2017), 478–485. https://doi.org/10.1016/j.jcis.2017.07.082.
• [18] Obot, I.B., Macdonald, D.D., Gasem, Z.M., Density functional theory (DFT) as a powerful tool for designing new organic corrosion inhibitors: Part 1: An overview, Corrosion Science, 99 (2015), 1–30. https://doi.org/10.1016/j.corsci.2015.01.037.
• [19] Leçe, H.D., Determination Of The Inhibitor Effect Of Some Macrocyclic Aromatic Schiff Base Compounds For The Corrosion Of Steel In Acidic Media, Ankara University, 2008.
• [20] Madkour, L.H., Kaya, S., Obot, I.B., Computational, Monte Carlo simulation and experimental studies of some arylazotriazoles (AATR) and their copper complexes in corrosion inhibition process, Journal of Molecular Liquids, 260 (2018), 351–374. https://doi.org/10.1016/j.molliq.2018.01.055.
• [21] Zhang, S.G., Lei, W., Xia, M.Z., Wang, F.Y., QSAR study on N-containing corrosion inhibitors: Quantum chemical approach assisted by topological index, Journal of Molecular Structure: THEOCHEM, 732 (1-3) (2005),173-182. https://doi.org/10.1016/j.theochem.2005.02.091.
• [22] Lashgari, M., Arshadi, M.R., Parsafar, G.A., A simple and fast method for comparison of corrosion inhibition powers between pairs of pyridine derivative molecules, Corrosion, 61 (8) (2005), 778–783. https://doi.org/10.5006/1.3278212.
• [23] Bhawsar, J., Jain, P., Valladares-Cisneros, M.G., Cuevas-Arteaga, C., Bhawsar, M.R., Quantum chemical assessment of two natural compounds: Vasicine and Vasicinone as Green Corrosion inhibitors, International Journal of Electrochemical Science, 13 (4) (2018), 3200–3209. https://doi.org/10.20964/2018.04.57.
• [24] Margrave, J.L., Electronegativity, Journal of the Chemical Society C: Organic, 83 (4) (1961), 3547-3551. https://doi.org/10.1039/j3970000x001.
• [25] Rajak, S.K., Islam, N., Ghosh, D.C., Modeling of the Chemico-Physical Process of Protonation of Molecules Entailing Some Quantum Chemical Descriptors, Journal of Quantum Information Science, 1 (2) (2011), 87-95. https://doi.org/10.4236/jqis.2011.12012.
• [26] Janak, J.F., Proof that ∂E/∂ni= in density-functional theory, Phys. Rev. B, 18 (12-15) (1978), 7165. https://doi.org/10.1103/PhysRevB.18.7165.
• [27] Von Szentpály, L., Studies on electronegativity equalization. Part 1. Consistent diatomic partial charges, Journal of Molecular Structure: THEOCHEM, 233, (6) (1991), 71-81. https://doi.org/10.1016/0166-1280(91)85055-C.
• [28] Yang, W., Parr, R.G., Hardness, softness, and the fukui function in the electronic theory of metals and catalysis, Proceedings of the National Academy of Sciences of the United States of America, 82 (20) (1985), 6723-6726. https://doi.org/10.1073/pnas.82.20.6723.
• [29] Parr, R.G., Szentpály, L. V., Liu, S., Electrophilicity index, Journal of the American Chemical Society,121, (9) (1999), 1922–1924. https://doi.org/10.1021/ja983494x.
• [30] Roy, D.R., Parthasarathi, R., Padmanabhan, J., Sarkar, U., Subramanian, V., Chattaraj, P.K., Careful scrutiny of the philicity concept, Journal of Physical Chemistry A, 110 (3) (2006), 1084–1093. https://doi.org/10.1021/jp053641v.
• [31] Pearson, D., Copeland, C.S., Benson, S.W., The Electrical Conductance of Aqueous Hydrochloric Acid in the Range 300 to 383°, Journal of the American Chemical Society, 85 (8) (1963), 1047–1049. https://doi.org/10.1021/ja00891a006.
• [32] Khadom, A.A., Quantum chemical calculations of some amines corrosion inhibitors/ copper alloy interaction in hydrochloric acid, Journal of Materials and Environmental Science, 8 (4) (2017), 1153–1160.
• [33] Messali, M., Larouj, M., Lgaz, H., Rezki, N., Al-Blewi, F.F., Aouad, M.R., Chaouiki, A., Salghi, R., Chung, I.M., A new schiff base derivative as an effective corrosion inhibitor for mild steel in acidic media: Experimental and computer simulations studies, Journal of Molecular Structure, 1168 (2018), 39–48. https://doi.org/10.1016/j.molstruc.2018.05.018.
• [34] Hamani, H., Douadi, T., Al-Noaimi, M., Issaadi, S., Daoud, D., Chafaa, S., Electrochemical and quantum chemical studies of some azomethine compounds as corrosion inhibitors for mild steel in 1M hydrochloric acid, Corrosion Science, 88 (2014),234-245. https://doi.org/10.1016/j.corsci.2014.07.044.
• [35] Zhang, K., Yang, W., Chen, Y., Xu, B., Yin, X., Liu, Y., Zuo, H., Enhanced inhibitive performance of fluoro-substituted imidazolium-based ionic liquid for mild steel corrosion in hydrochloric acid at elevated temperature, Journal of Materials Science, 53 (20) (2018), 14666–14680. https://doi.org/10.1007/s10853-018-2616-6.
• [36] Lukovits, I., Kálmán, E., Zucchi, F., Corrosion inhibitors - Correlation between electronic structure and efficiency, Corrosion, 57 (1) (2001), 3-8. https://doi.org/10.5006/1.3290328.
• [37] Fitoz, A., Nazır, H., Özgür (nee Yakut), M., Emregül, E., Emregül, K.C., An experimental and theoretical approach towards understanding the inhibitive behavior of a nitrile substituted coumarin compound as an effective acidic media inhibitor, Corrosion Science, 133 (2018), 451–464. https://doi.org/10.1016/j.corsci.2017.10.004.
• [38] Qiang, Y., Zhang, S., Xu, S., Li, W., Experimental and theoretical studies on the corrosion inhibition of copper by two indazole derivatives in 3.0% NaCl solution, Journal of Colloid and Interface Science, 472 (2016), 52-59. https://doi.org/10.1016/j.jcis.2016.03.023.
• [39] Obot, I.B., Obi-Egbedi, N.O., Theoretical study of benzimidazole and its derivatives and their potential activity as corrosion inhibitors, Corrosion Science, 52 (2) (2010), 657-660. https://doi.org/10.1016/j.corsci.2009.10.017.
• [40] Verma, C., Quraishi, M.A., Singh, A., 5-Substituted 1H-tetrazoles as effective corrosion inhibitors for mild steel in 1 M hydrochloric acid, Journal of Taibah University for Science, 10 (5) (2016), 718–733. https://doi.org/10.1016/j.jtusci.2015.10.005.
• [41] Abd El-Lateef, H.M., Experimental and computational investigation on the corrosion inhibition characteristics of mild steel by some novel synthesized imines in hydrochloric acid solutions, Corrosion Science, 92 (2015),104-117. https://doi.org/10.1016/j.corsci.2014.11.040.
• [42] Obot, I.B., Gasem, Z.M., Theoretical evaluation of corrosion inhibition performance of some pyrazine derivatives, Corrosion Science, 83 (2014), 359-366. https://doi.org/10.1016/j.corsci.2014.03.008.
• [43] Pearson, J.C., Lemons, D., McGinnis, W., Modulating Hox gene functions during animal body patterning, Nature Reviews Genetics, 6 (2005), 893–904. https://doi.org/10.1038/nrg1726.
• [44] Chattaraj, P.K., Sarkar, U., Roy, D.R., Electrophilicity index, Chemical Reviews, 106 (6) (2006), 2065–2091. https://doi.org/10.1021/cr040109f.
• [45] Wazzan, N., Al-mhyawi, S., Application of newly quiniline-3-carbonitriles as corrosion inhibitors on mild steel in 1.0 M HCl: Electrochemical measurements, HF and DFT/B3LYP calculations, International Journal of Electrochemical Science, 12 (2017) 9812 – 9828. https://doi.org/10.20964/2017.10.81.
• [46] Zhang, W., Li, H.J., Wang, Y., Liu, Y., Gu, Q.Z., Wu, Y.C., Gravimetric, electrochemical and surface studies on the anticorrosive properties of 1-(2-pyridyl)-2-thiourea and 2-(imidazol-2-yl)-pyridine for mild steel in hydrochloric acid, New Journal of Chemistry, 42 (2018), 12649-12665. https://doi.org/10.1039/c8nj01762j.