Cover Image

Copper corrosion inhibition in nitric acid solution by 2-(1,3-dihydrobenzimidazol-2-ylidene) -3-oxo-3-(pyridin-3-yl) propanenitrile: Gravimetric, Quantum chemical and QSPR studies

Tigori Mougo André, Aboudramane Koné, Koua N’zebo René, Mamadou Yeo, Paulin Marius Niamien

Abstract


The metal corrosion threat in the metallurgical industry is becoming increasingly important. So in this work, the inhibition properties of 2-(1,3-dihydrobenzimidazol-2-ylidene)-3-oxo-3-(pyridin-3-yl) propanenitrile for copper corrosion in 1 M nitric acid medium were evaluated by mass loss technique, density functional theory (DFT) and quantitative structure-property relationship (QSPR) model. The results show that this compound was excellent anticorrosive properties with a maximum inhibition efficiency of 89.39 % for a concentration of 0.2 mM at 323 K. The inhibition efficiency increases with increasing temperature and inhibitor concentration. Adsorption isotherms reported that the molecule adsorbs on copper surface according to Langmuir isotherm. Thermodynamic adsorption and activation parameters were determined and analyzed. They revealed spontaneous adsorption and a strong interaction between the molecule and copper surface. DFT calculations at the B3LYP level with 6-31G(d,p) and 6-311G(d,p) basis set permitted to explain the electronic exchanges between molecule and copper, thus justifying the experimentally obtained inhibition efficiency values. A local reactivity study of molecules indicated that N (29) and C (7) atoms are the likely sites for nucleophilic and electrophilic attacks, respectively. In addition, QSPR model was used to correlate experimental inhibition efficiency with the descriptor parameters of the studied molecule, and it is found that the calculated inhibition efficiencies are close to experimental inhibition efficiencies. Finally, this study showed a good correlation between theoretical and experimental data.

Full Text:

PDF

References


- L. Zhou, S. Zhang, B. Tan, L. Feng, B. Xiang, F. Chen, W. Li, B. Xiong, T. Song, Phenothiazine drugs as novel and eco-friendly corrosion inhibitors for copper in sulfuric acid solution, Journal of the Taiwan Institute of Chemical Engineers, 2020, 113, 253–263.

- J. Zhang, L. Zhang, G. Tao, A novel and high-efficiency inhibitor of 5-(4-methoxyphenyl)-3h-1,2-dithiole-3-thione for copper corrosion inhibition in sulfuric acid at different temperatures, Journal of Molecular Liquids, 2018, 272, 369-379.

- A. Hedin, J. Johansson, F. King, Comment on Corrosion-induced microstructure degradation of copper in sulfide-containing simulated anoxic groundwater studied by synchrotron high-energy X-ray diffraction and ab-initio density functional theory calculation, Corrosion Science, 2022, 199, 110182.

- A. Jmiai, A. Tara, S. El Issami, M. Hilali, O. Jbara, L. Bazzi, A new trend in corrosion protection of copper in acidic medium by using Jujube shell extract as an effective green and environmentally safe corrosion inhibitor: Experimental, quantum chemistry approach and Monte Carlo simulation study, Journal of Molecular Liquids, 2021, 322, 114509, 1-36.

- S. Echihi, N. Benzbiri, M. E. Belghiti, M. ElFal, M. Boudali, E. M. Essassi, A. Guenbour, A. Bellaouchou, M. Tabyaoui, M. Azzib, Corrosion inhibition of copper by pyrazole pyrimidine derivative in synthetic seawater: Experimental and theoretical studies, Materialstoday Proceedings, 2021, 37(2), 3958-3966.

- R. Laggoun, M. Ferhat, B. Saidat, A. Benghia, A. Chaabani, Effect of p-toluenesulfonyl hydrazide on copper corrosion in hydrochloric acid solution. Corrosion Science, 2020, 165, 108363.

- L. Guo, B. Tan, X. Zuo, W. Li, S. Leng, X. Zheng, Eco-friendly food spice 2- Furfurylthio-3-methylpyrazine as an excellent inhibitor for copper corrosion in sulfuric acid medium, Journal of Molecular Liquids, 2020, 317, 113915.

- L. Zhou, S. Zhang, B. Tan, Li Feng, B. Xiang, F. Chen, Weining Li, B. Xiong, T. Song, Phenothiazine drugs as novel and eco-friendly corrosion inhibitors for copper in sulfuric acid solution, Journal of the Taiwan Institute of Chemical Engineers, 2020, 113, 253-263.

- A. K. Singh, S. Mohapatra, B. Pani, Corrosion Inhibition Effect of Aloe Vera gel: Gravimetric and Electrochemical Study, Journal of Industrial and Engineering Chemistry, 2016, 25, 288-297.

- M. A. Deyab, Egyptian Licorice Extract as a Green Corrosion Inhibitor for Copper in Hydrochloric Acid Solution, Journal of Industrial and Engineering Chemistry, 2015, 25, 384-389.

- B. S. Mahdi, H. S. S. Aljibori, M. K. Abbass, W. K. Al-Azzawi, A. H. Kadhum, M. M. Hanoon, W. N. R. W. Isahak, A. A. Al-Amiery, H. Sh. Majdi, Gravimetric analysis and quantum chemical assessment of

-aminoantipyrine derivatives as corrosion inhibitors, International Journal of Corrosion and Scale Inhibition, 2022, 11(3), 1191–1213

- K. El Mouaden, D. S. Chauhan, M. A. Quraishi, L. Bazzi, M. Hilali, Cinnamaldehyde-modified chitosan as a bio-derived corrosion inhibitor for acid pickling of copper: Microwave synthesis, experimental and computational study, International Journal of Biological Macromolecules, 2020, 164, 3709–3717.

- S. Smagill, C. Shields, C. L. Sears, M. Choti, W. G. Merz, Résistance croisée aux dérivés triazolés chez Candida sp. : Observation, fréquence dans les isolats sanguins et implications pour les traitements antifongiques Journal de mycologie médicale, 2007, 17 (1), S1-S10.

- V. Djohan, K. E. Angora, A. H. Vanga-Bosson, A. Konaté, F. K. Kassi, W. Yavo, P. C. Kiki Barro, In vitro susceptibility of vaginal Candida albicans to antifungal drugs in Abidjan (Ivory Coast), Journal de Mycologie Médicale, 2012, 22 (2), 129-133.

- H.J. Al-Fahemi, M.Abdallah, Elshafie A.M.Gad, B.A.A.L.Jahdaly, Experimental and theoretical approach studies for melatonin drug as safely corrosion inhibitors for carbon steel using DFT, Journal of Molecular Liquids,2016,222, 1157-1163

- M. Abdallah, A. Al Bahira, H. M. Altass, A. Fawzy, N. El Guesmi, A. S. Al-Gorair, F. B.Warad, A. Zarrouk, Anticorrosion and adsorption performance of expired antibacterial drugs on Sabic iron corrosion in HCl solution: Chemical, electrochemical and theoretical approach, Journal of Molecular Liquids, 2021, 330, 115702, 1-15.

- H. A. Almashhadani, M. K. Alshujery, M. Khalil, M. M. Kadhemd, A. A. Khadom Corrosion inhibition behavior of expired diclofenac Sodium drug for Al 6061 alloy in aqueous media: Electrochemical, morphological, and theoretical investigations, Journal of Molecular Liquids, 2021, 117656

- M. A. Tigori, A. Kouyaté, V. Kouakou, P. M. Niamien, A. Trokourey, Computational approach for predicting the adsorption properties and inhibition of some antiretroviral drugs on copper corrosion in HNO3, European Journal of Chemistry, 2020, 11(3), 235-244.

- M. A. Tigori, A. Kouyaté, V. Kouakou, P. M. Niamien, A. Trokourey, Inhibition Performance of Some Sulfonylurea on Copper Corrosion in Nitric Acid Solution, Evaluated Theoretically by DFT Calculations, Open Journal of Physical Chemistry, 2020,10(3),139-157.

- F. J. Rodríguez-Gómez, M. P. Valdelamar, A. E. Vazquez, P. D. Valle Perez, R. Mata, A. Miralrio, M. Castro, Mycophenolic acid as a corrosion inhibitor of carbon steel in 3% wt. NaCl solution. An experimental and theoretical study, Journal of Molecular Structure, 2019, 1183, 168-181.

- L. Guo, S. Zhu, S. Zhang, Q. He, W. Li, Theoretical studies of three triazole derivatives as corrosion inhibitors for mild steel in acidic medium, Corrosion Science, 2014, 87, 366-375.

- J. A. Van Allan, B. D. Deagon, Organic Syntheses Collect, John Wiley & Sons, New York, NY, USA, 4, 1963.

- N. Perin, L. Uzelac, I. Piantanida, G. Karminski-Zamola, M. Kralj, M. Hranjec, Novel biologically active nitro and amino substituted benzimidazo[1,2-a]quinolines Bioorganic & Medicinal Chemistry, 2011,19 (21), 6329-6339

- M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V.Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J.Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T.Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M.Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi,

J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox,

J. B.Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi,C. Pomelli, J. W. Ochterski,

R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J.Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and A. D. J. Fox,Gaussian, Inc., Wallingford, 09.2009

- A. D. Becke, Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction, The Journal of Chemical Physics, 1992, 96, 2155-2160.

- C. Lee, W. Yang, R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review B., 1988, 37, 785-789.

- H. Allal, Y. Belhocine, E. Zouaoui, Computational study of some thiophene derivatives as aluminium corrosion inhibitors, Journal of Molecular Liquids, 2018, 265, 668–678.

- T. Koopmans, Uber die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms, Physica

A: Statistical Mechanics and its Applications, 1934, 1(1–6), 104–113.

- H. Al-Fahemi, M. Abdallah, E. A. M. Gad, B. A. A. L. Jahdaly, Experimental and theoretical approach studies for melatonin drug as safely corrosion inhibitors for carbon steel using DFT, Journal of Molecular Liquids, 2016, 222, 1157–1163.

- R. G. Pearson, "Hard and soft acids and bases-the evolution of a chemical concept," Coordination Chemistry Reviews, 1990, 100, 403–425.

- H. B. Michaelson, The work function of the elements and its periodicity, Journal of Applied Physics, 1977, 48, 4729-4733.

- M. J. S.Dewar, E. G.Zoebisch, E. F. Healy, J. P. Stewart, Development and use of quantum mechanical molecular models, 76, AM1: a new general-purpose quantum mechanical molecular model, Journal of the American Chemical Society, 1985, 107(13), 3902-3909.

- R. G. Parr, L. V. Szentpaly, S. Liu, Electrophilicity index,' Journal of the American Chemical Society, 1999, 121(9), 1922–1924.

- J. L. Gazquez, A. Cedillo, A. Vela, Electrodonating and electroaccepting powers, The Journal of Physical Chemistry, 2007, 111, 1966-1970.

- A. Berrissoul, A. Ouarhach, F. Benhiba, A. Romane, A. Zarrouk, A. Guenbour, B. Dikici, A. Dafali, Evaluation of Lavandula mairei extract as green inhibitor for mild steel corrosion in 1 M HCl solution. Experimental and theoretical approach, Journal of Molecular Liquids, 2020, 313, 113493.

- C. Morell, A. Grand, A. Toro-Labbé, New Dual Descriptor for Chemical Reactivity, Journal of Physical Chemistry. A, 2005, 109, 205-212.

- J. I. Martínez-Araya, Why Is the Dual Descriptor a More Accurate Local Reactivity Descriptor than Fukui Functions, Journal of Mathematical Chemistry, 2015, 5, 451-465.

- N. O. Obi-Egbedi, I. B. Obot, M. I. El-Khaiary, S. A. Umoren, E. E. Ebenso, Computational Simulation and Statistical Analysis on the Relationship Between Corrosion Inhibition Efficiency and Molecular Structure of Some Phenanthroline Derivatives on Mild Steel Surface, International Journal of electrochemical science, 2011, 6, 5649 – 5675.

- I. Lukovits, E. F. Kalman, Corrosion Inhibitors—Correlation between Electronic Structure and Efficiency, Corrosion, 2001, 57(1), 3-8.

- Z. Žaklina, B. TasićMarija, P. Mihajlović, M. B. Radovanović, A. T. Simonović, M. M. Antonijević, Experimental and theoretical studies of paracetamol as a copper corrosion inhibitor, Journal of Molecular Liquids, 2021, 327, 114817, 1-9.

- A. Fawzy, I. A. Zaafarany, H. M. Ali, M. Abdallah, New synthesized amino acids-based surfactants as efficient inhibitors for corrosion of mild steel in hydrochloric acid medium: kinetics and thermodynamic approach, International Journal of electrochemical science, 2018, 13, 4575–4600.

- N. Benzbiria, S. Echihi, M. E. Belghiti, A. Thoume, A. Elmakssoudi, A. Zarrouk, M. Zertoubi, M. Azzi Novel synthesized benzodiazepine as efficient corrosion inhibitor for copper in 3.5% NaCl solution, Materials Today: Proceedings, 2021, 37(3), 3932-3939.

- H. Huang, X. Guo, The relationship between the inhibition performances of three benzo derivatives and their structures on the corrosion of copper in 3.5 wt.% NaCl solution, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2020, 598, 124809.

- R. Farahati, H. Behzadi, S. M. Mousavi-Khoshdel, A. Ghaffarinejad, Evaluation of corrosion inhibition of 4-(pyridin-3-yl) thiazol-2-amine for copper in HCl by experimental and theoretical studies, Journal of Molecular Structure, 2020, 1205, 127658.

- S. O. Adejo, M. M. Ekwenchi, Resolution of adsorption characterization ambiguity through the Adejo-Ekwenchi adsorption isotherm: a case study of leaf extract of Hyptis suaveolen point as green corrosion inhibitor of corrosion of mild steel in 2 M HCl, Journal of Emerging Trends in Engineering and Applied Sciences, 2014, 5, 201- 205.

- M. Abdallah, A. Fawzy, A. Al Bahir, The effect of expired acyclovir and omeprazole drugs on the inhibition of Sabic Iron corrosion in HCl solution, International Journal of electrochemical science15, 2020, 15, 4739–4753.

- Y. Qiang, S. Zhangao, S. Yan, X. Zou, S. Chen, Three indazole derivatives as corrosion inhibitors of copper in a neutral chloride solution, Corrosion Science, 2017, 126, 295-304.

- M. Khattabi, F. Benhiba, S. Tabti, A. Djedouani, A. El Assyry, R. Touzani, I. Warad, H. Oudda, A. Zarrouk, Performance and computational studies of two soluble pyran derivatives as corrosion inhibitors for mild steel in HCl, Journal of Molecular Structure, 2019, 1196, 231-244

- A Singh, K. R Ansari, A. Kumar, W. Liu, C. Songsong, Y. Liu, Electrochemical, surface and quantum chemical studies of novel imidazole derivatives as corrosion inhibitors for J55 steel in a sweet corrosive environment, Journal of Alloys and Compounds, 2017, 712, 121-133.

- R. Padash, M. Rahimi Nasrabadi, A. Shokuhi Rad, A. Sobhani Nasab, T. Jesionowski, H. Ehrlich, A theoretical study of two novel Schiff bases as inhibitors of carbon steel corrosion in acidic medium, Applied Physics A, 2019,125,1-11

- Z. Z. Tasić, M. B. Petrović Mihajlović, A. T. Simonović, M. B. Radovanović, M. M. Antonijević, Ibuprofen as a corrosion inhibitor for copper in synthetic acid rain solution, Scientific Reports, 2019, 9(1), 14710.

- B. Hamrahi, A. Khanlarkhani, S. Morteza Madani, A. Fattah alhosseini, S. O. Gashti, Evaluation of Henna Extract Performance on Corrosion Inhibition of API 5L Steel in H2S Containing Medium and DFT Quantum Computing of Its Constituents, Metals and Materials International, 2021, 27, 4463–4476.




DOI: http://dx.doi.org/10.13171/mjc02209131649tigori

Copyright (c) 2022 Mediterranean Journal of Chemistry