Theoretical Evaluation of the Corrosion Inhibition Performance of an Organic Heterocyclic Compound
Keywords:5-Chloroisatin derivative, Corrosion inhibitor, DFT, Fukui function, Experiment, Theoretical studies
The corrosion inhibition performance of a corrosion inhibitor on mild steel in phosphoric acid, namely 5-chloro-1-(2-(dimethylamino) ethyl) indoline-2,3-dione (TZCDI), was theoretically evaluated using density functional theory (DFT) at the B3LYP/6-31G+(d,p) level for all atoms by Gaussian 09W program. The quantum chemical properties, such as highest occupied molecular orbital energy (EHOMO), lowest unoccupied molecular orbital energy (ELUMO) energy gap (∆Egap), dipole moment (μ), total hardness (η), and electronegativity (χ), were studied, and these descriptors were discussed in connection to the experimental inhibitory efficiency. The local reactivity was analyzed through the Fukui function in order to compare the possible sites for nucleophilic and electrophilic attacks. Accordingly, all data obtained using various theoretical calculation techniques were consistent with experiments.
T Liu, Z Guo, Z Zeng, N Guo, Y Lei, T Liu, S Sun, X Chang, Y Yin and X Wang. Marine bacteria provide lasting anticorrosion activity for steel via biofilm-induced mineralization. ACS Appl. Mater. Interfaces 2018; 10, 40317-27.
Z Tribak, MK Skalli and O Senhaji. Anticorrosion activity for some 5-Chloroisatin derivatives. Éditions Universitaires Européennes. German, 2017, p. 1-46.
K Babić-Samardžija, KF Khaled and N Hackerman. N-heterocyclic amines and derivatives as corrosion inhibitors for iron in perchloric acid. Anti Corros. Method. Mater. 2005; 52, 11-21.
Z Tribak, YK Rodi, H Elmsellem, I Abdel-Rahman, A Haoudi, MK Skalli, Y Kadmi, B Hammouti, MA Shariati and EM Essassi. 5-chloro-1-octylindoline-2,3-dione as a new corrosion inhibitor for mild steel in hydrochloric acid solution. J. Mater. Environ. Sci. 2017; 8, 1116-27.
Z Tribak, Y Kharbach, A Haoudi, MK Skalli, YK Rodi, ME Azzouzi, A Aouniti, B Hammouti and O Senhaji. Study of new 5-chloro-isatin derivatives as efficient organic inhibitors of corrosion in 1M HCl medium: Electrochemical and SEM studies. J. Mater. Environ. Sci. 2016; 7, 2006-20.
SK Bhati and A Kumar. Synthesis of new substituted azetidinoyl and thiazolidinoyl-1,3,4-thiadiazino (6,5-b) indoles as promising anti-inflammatory agents. Eur. J. Med. Chem. 2008; 43 2323-30.
Y Zhou, J Liu, M Zheng, S Zheng, C Jiang, X Zhou, D Zhang, J Zhao, D Ye, M Zheng, H Jiang, D Liu, J Cheng and H Liu. Structural optimization and biological evaluation of 1,5-disubstituted pyrazole-3-carboxamines as potent inhibitors of human 5-lipoxygenase. Acta Pharm. Sin. B 2016; 6 32-45.
K Bettayeb, OM Tirado, S Marionneau-Lambot, Y Ferandin, O Lozach, JC Morris, S Mateo-Lozano, P Drueckes, C Schächtele, MHG Kubbutat, F Liger, B Marquet, B Joseph, A Echalier, JA Endicott, V Notario and L Meijer. Meriolins, a new class of cell death-inducing kinase inhibitors with enhanced selectivity for cyclin-dependent kinases. Cancer Res. 2007; 67, 8325-34.
Z Tribak, OE Amin, MK Skalli, O Senhaji, YK Rodi and M Iraqui. N-alkylation methods, characterization and evaluation of antibacterial activity of some novel 5-chloroisatin derivatives. Int. J. Eng. Res. Appl. 2017; 7, 21-4.
Z Tribak, OE Amin, MK Skalli, O Senhaji, YK Rodi and MH Iraqui. Synthesis, characterization, and antibacterial activity of some novel 5-chloroisatin derivatives. Int. J. Eng. Res. Appl. 2017; 7, 66-70.
Z Tribak, MK Skalli, A Haoudi, YK Rodi, O Senhaji and EM Essassi. Cyclocondensation, characterization and antibacterial activities of novel 5-chloro-1HIndole-2,3-dione derivatives. J. Appl. Microbiol. Biochem. 2018; 2, 1-4.
Z Tribak, A Chda, MK Skalli, A Haoudi, YK Rodi, O Senhaji, EM Essassi, R Bencheikh and KE Abida. Theoretical approach using DFT and muscle relaxant effects of 5-chloroisatin derivatives. Int. J. Chem. Technol. 2018; 2, 105-15.
ER El-Sawy, AH Mandour, SM El-Hallouty, KH Shaker and HM Abo-Salem. Synthesis, antimicrobial and anticancer activities of some new N-methylsulphonyl and N-benzenesulphonyl-3-indolyl heterocycles: 1st Cancer Update. Arab. J. Chem. 2013; 6, 67-78.
Z Tribak, R Ghibate, MK Shalli, YK Rodi and O Senhaji. Experimental and theoretical study for corrosion inhibition in 1M HCl solution by new 5-chloroisatin derivative. Int. J. sci. Technol. Eng. 2016; 3, 257-62.
Z Tribak, MK Skalli, A Haoudi, YK Rodi and O Senhaji. DFT, quantum chemical study and biological effects of a heterocyclic molecular. J. Biotech. Biores. 2019; 1, 1-5.
Z Tribak, MK Skalli, A Haoudi, YK Rodi and O Senhaji. Experimental approach, computational DFT investigation and a biological activity in the study of an organic heterocyclic compound. Arc. Org. Inorg. Chem. Sci. 2019; 4, 458-64.
Z Tribak, A Haoudi, YK Rodi, H Elmsellem, MK Skalli, Y Ouzidan, A Mazzah and EM Essassi. Synthesis and reactivity of new heterocyclic systems derived from 5-chloro-1H-indole-2,3-dione. Moroccan J. Chem. 2016; 4, 1157-63.
Z Tribak, A Haoudi, MK Skalli, KY Rodi, ME Azzouzi, A Aouniti, B Hammouti and O Senhaji. 5-Chloro-1H-indole-2,3-dione derivative as corrosion inhibitor for mild steel in 1M H3PO4: Weight loss, electrochemical and SEM studies. J. Mater. Environ. Sci. 2017; 8, 299-309.
M Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, G Scalmani, V Barone and B Mennucci. Ga Petersson, Gaussian 09, revision a. 02, gaussian, Wallingford, CT. 200, 2009.
J Poater, M Duran and Miquel Solà. Parametrization of the Becke3-LYP hybrid functional for a series of small molecules using quantum molecular similarity techniques. J. Comput. Chem. 2001; 22, 1666-78.
Z Tribak, MK Skalli, O Senhaji and YK Rodi. Experimental and theoretical DFT study on synthesis of novel 5-chloroisatin derivatives via 1,3-dipolar cycloaddition reactions between allyl-5-chloroindoline-2,3-dione and 4-chlorobenzaldoxime. Int. J. Appl. Chem. 2017; 4, 1-6.
Z Tribak, MK Skalli, O Senhaji and YK Rodi. Synthesis, structural characterization and comparison of experimental and theoretical results by DFT level of molecular structures of 1,2,3-triazoles derived from 5-chloroisatin. Int. J. Adv. Chem. 2017; 5, 91-5.
T Fievez, N Sablon, FD Proft, PW Ayers and P Geerlings. Calculation of Fukui functions without differentiating to the Number of electrons. 3. local Fukui function and dual descriptor. J. Chem. Theor. Comput. 2008; 1, 1065-72.
A Dwivedi, V Baboo and A Bajpai. Fukui function analysis and optical, electronic, and vibrational properties of tetrahydrofuran and its derivatives: A complete quantum chemical study. J. Theor. Chem. 2015; 2015, 1-11.
Z Tribak, MK Skalli, O Senhaji, YK Rodi, A Haoudi and EM Essassi. A Review on recent advances and applications of 5-chloroisatin and its derivatives in design and synthesis of new organic compounds. Am. Int. J. Res. Formal Appl. Nat. Sci. 2017; 19, 41-50.
Z Tribak, YK Rodi, A Haoudi, EM Essassi, F Capet and H Zouihri. 5-chloro-1-methylindoline-2, 3-dione. IUCrData 2016; 1, 1-3.
Z Tribak, YK Rodi, A Haoudi, EM Essassi, F Capet and H Zouihri. 1-allyl-5-chloroindoline-2, 3-dione. IUCrData 2016; 1, 1-2.
Z Tribak, YK Rodi, A Haoudi, EM Essassi, F Capet and H Zouihri. 1-(12-Bromododecyl)-5-chloroindoline-2,3-dione. IUCrData 2016; 1, 1-2.
Z Tribak, YK Rodi, A Haoudi, EM Essassi, F Capet and H Zouihri. 1-Benzyl-5-chloroindoline-2, 3-dione. IUCrData 2016; 1, 1-2.
V Sivakumar, K Velumani and S Rameshkumar. Colocid dye - a potential corrosion inhibitor for the corrosion of mild steel in acid media. Mater. Res. 2018; 21, 1-10.
Z Tribak, YK Rodi, H Elmsellem, A Haoudi, MK Skalli, Y Ouzidan, O Senhaji, NK Sebbar, EM Essassi and B Hammouti. The role of 1-allyl-5-chloro-indoline-2,3-dione on the corrosion inhibition of steel in HCL media. J. Mar. Chim. Heterocycl. 2017; 16, 157-65.
MO Abdulazeez, AK Oyebamiji and B Semire. DFT and QSAR study of corrosion inhibition on 3, 5-di-substituted pyrazole derivatives with heteroatom on position one. Leban. Sci. J. 2016; 17, 217-32.
L Guo, S Kaya, IB Obot, X Zheng and Y Qiang. Toward understanding the anticorrosive mechanism of some thiourea derivatives for carbon steel corrosion: A combined DFT and molecular dynamics investigation. J. Colloid Interface Sci. 2017; 15, 478-85.
GM Al-Mazaideh, TS Ababneh, KH Abu-Shandi, RMAQ Jamhour, HJA Salman, AM Al-Msiedeen and SM Khalil. DFT calculations of Mesembryanthemum nodiflorum compounds as corrosion inhibitors of aluminum. Phys. Sci. Int. J. 2016; 12, 1-7.
J Bhawsar, PK Jain, P Jain and MR Bhawsar. Computational study of corrosion potential of Ciprofloxacin drug: DFT approach. Asian J. Res. Chem. 2014; 7, 386-9.
EE Elemike, DC Onwudiwe, HU Nwankwo and EC Hosten. Synthesis, crystal structure, electrochemical and anti-corrosion studies of Schiff base derived from o-toluidine and o-chlorobenzaldehyde. J. Mol. Struct. 2017; 1136, 253-62.
S Gosav, N Paduraru, D Maftei, ML Birsa and M Praisler. Quantum chemical study of a derivative of 3-substituted dithiocarbamic flavanone, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2017; 172, 115-25.
B Gómez, NV Likhanova, MA Domínguez-Aguilar, R Martínez-Palou, A Vela and L Ga. Quantum chemical study of the inhibitive properties of 2-pyridyl-azoles. J. Phys. Chem. B 2006; 110, 8928-34.
How to Cite
Copyright (c) 2020 Walailak University
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.