Synthesis, Corrosion Inhibition Efficiency in Acidic Media, and Quantum Chemical Studies of Some Hydrazine Derivatives
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Keywords:
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Hydrazone, MOE, Tafel Plot, Dipole Moment
Abstract
In this work, four hydrazone Schiff base derivatives N-(2,4-Dinitro-phenyl)-N’-(1H-pyrrol-2-ylmethylene)-hydrazine (1a), N-Benzo [1,3] dioxol-5-ylmethylene-N’-(2,4-dinitro-phenyl)-hydrazine (1b), (E)-5-((2-(2,4-dinitrophenyl)hydrazono)methyl)-2-hydroxybenzoic acid (1c) and (E)-1-(2,4-dinitrophenyl)-2-(2-methoxybenzylidene)hydrazine (1d) were synthesized by reaction of four aldehydes namely pyrrole-2-carboxaldehyde, piperonal, 5-formylsalicylic acid, and o-vanillin with 2,4-dinitrophenyl hydrazine to produce the final compounds 1a, 1b, 1c, and 1d, respectively. These four compounds were investigated as corrosion inhibitors in aqueous mild acidic static solution. FTIR, HNMR, and elemental analysis were used to elucidate the chemical structure of the synthesized inhibitors. Using potential dynamic polarization measurements, these inhibitors’ efficiency in preventing C-steel corrosion in 1.00 M HCl was studied. The results of the experiments revealed that 1×10−3 M is the ideal concentration for 1a, 1b, 1c, and 1d, and that the corresponding inhibition efficiencies for these subunits were 80.70%, 91.30%, 91.34, and 88.80%, respectively. The best corrosion inhibitors were compounds 1b and 1c. Furthermore, studies suggested that these substances are mixed-type inhibitors and that the efficiency of the inhibition is strongly correlated with their quantity. Quantum paraments included Dipole moment, energy band gap (ΔE), value of energy of lowermost unoccupied molecular orbital (ELUMO), and energy of high most occupied molecular orbital (EHOMO) using Molecular Operating Environment MOE, Gaussian, and HyperChem software packages were determined which demonstrated strong agreement between algorithmic and practical findings.
References
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Gomathi, V. and R. Selvameena (2022). Synthesis, Structural Analysis and Antimicrobial Screening of Mn (II) Complexes of Schiff Bases. Journal of the Mexican Chemical Society, 66(1); 70–78
Guo, X., J. Wang, L. Huang, Y. Wang, L. Ma, D. Zhang, and L. Ma (2022). Corrosion Inhibition and Adsorption Process of 3-Amino-5-Mercapto-1, 2, 4-Triazole on Aluminium Alloy: Experimental and Theoretical Studies. Frontiers in Materials, 9; 874899
Hassan, A., M. S. Numin, K. Jumbri, K. E. Kee, N. Borhan, N. M. R. Nik Mohamed Daud, A. Mohammed Nor, M. F. Suhor, and R. Abdul Wahab (2023). Density Functional Theory Studies on New Possible Biobased Gemini Corrosion Inhibitors Derived from Fatty Hydrazide Derivatives. ACS Omega, 8(26); 23945–23952
Jabeen, M. (2022). A Comprehensive Review on Analytical Applications of Hydrazone Derivatives. Journal of the Turkish Chemical Society Section A: Chemistry, 9(3); 663–698
Jasim, E. Q., E. A. Alasadi, R. H. Fayadh, and M. A. Muhamman-Ali (2020). Synthesis and Antibacterial Evaluation of Some Azo-Schiff Base Ligands and Estimation the Cadmium Metal by Complexation. Systematic Reviews in Pharmacy, 11(6); 677–687
Jasim, E. Q., M. A. Ma, and R. H. Fayadh (2017). Synthesis and Characterization of Some Thiadiazole Compounds as New Corrosion Inhibitors for Mild Steel in Cooling Water. Asian Journal of Chemistry, 29(11); 2361–2365
Jasim, E. Q., M. A. Muhammad-Ali, and A. Almakki (2023). Synthesis, Characterization, and Antibacterial Activity of Some Mesalazine Derivatives. Science and Technology Indonesia, 8(3); 338–343
Kuraimid, Z. K., D. S. Abid, and A. E.-A. S. Fouda (2023). Synthesis and Characterization of a Novel Quaternary Ammonium Salt as a Corrosion Inhibitor for Oil-Well Acidizing Processes. ACS Omega, 8(30); 27079–27091
Lgaz, H., A. Chaouiki, M. R. Albayati, R. Salghi, Y. El Aoufir, I. H. Ali, M. I. Khan, S. K. Mohamed, and I.-M. Chung (2019). Synthesis and Evaluation of Some New Hydrazones As Corrosion Inhibitors for Mild Steel in Acidic Media. Research on Chemical Intermediates, 45; 2269–2286
Maniak, H., M. Talma, and M. Giurg (2021). Inhibitory Potential of New Phenolic Hydrazide Hydrazones with a Decoy Substrate Fragment Towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies. International Journal of Molecular Sciences, 22(22); 12307
Mazlan, N., K. Jumbri, M. A. Kassim, R. A. Wahab, and M. B. A. Rahman (2022). Density Functional Theory and Molecular Dynamics Simulation Studies of Bio-Based Fatty Hydrazide-Corrosion Inhibitors on Fe (1 1 0) in Acidic Media. Journal of Molecular Liquids, 347; 118321
Muhammad, A. A., T. A. Nyijime, and A. S. Muhammad (2020). Density Functional Theory and Molecular Dynamic Simulation Studies on the Corrosion Inhibition of Some Thiosemicarbazide Derivatives on Aluminum Metal. Journal of Applied Surfaces and Interfaces, 8(1-3); 7–14
Muhammad-Ali, M. A., E. Q. Jasim, and A. H. Al-Saadoon (2023). Synthesis, Antibacterial Evaluation, and Docking Studies of Some Azo Compounds and Schiff Bases Derived from Sulfonamide. Journal of Medicinal and Chemical Sciences, 6(9); 2128–2139
Njong, R. N., B. N. Ndosiri, E. N. Nfor, and O. E. Offiong (2018). Corrosion Inhibitory Studies of Novel Schiff Bases Derived from Hydralazine Hydrochloride on Mild Steel in Acidic Media. Open Journal of Physical Chemistry, 8(1); 15–32
Obot, I., A. A. Bahraq, and A. H. Alamri (2022). Density Functional Theory and Molecular Dynamics Simulation of the Corrosive Particle Diffusion in Pyrimidine and Its Derivatives Films. Computational Materials Science, 210; 111428
Oukhrib, R., Y. Abdellaoui, A. Berisha, H. Abou Oualid, J. Halili, K. Jusufi, M. Ait El Had, H. Bourzi, S. El Issami, and F. A. Asmary (2021). DFT, Monte Carlo and Molecular Dynamics Simulations for the Prediction of Corrosion Inhibition Efficiency of Novel Pyrazolylnucleosides on Cu (111) Surface in Acidic Media. Scientific Reports, 11(1); 3771
Oyeneyin, O. E., N. D. Ojo, N. Ipinloju, E. B. Agbaffa, and A. V. Emmanuel (2022). Investigation of the Corrosion Inhibition Potentials of Some 2-(4-(substituted) Arylidene)-1H-Indene-1, 3-Dione Derivatives: Density Functional Theory and Molecular Dynamics Simulation. Beni-Suef University Journal of Basic and Applied Sciences, 11(1); 1–14
Packialakshmi, P., P. Gobinath, D. Ali, S. Alarifi, R. Gurusamy, A. Idhayadhulla, and R. Surendrakumar (2022). New Chitosan Polymer Scaffold Schiff Bases As Potential Cytotoxic Activity: Synthesis, Molecular Docking, and Physiochemical Characterization. Frontiers in Chemistry, 9; 796599
Parvarinezhad, S. and M. Salehi (2021). Synthesis, Characterization, Anti-Proliferative Activity and Chemistry Computation of DFT Theoretical Methods of Hydrazine-Based Schiff Bases Derived from Methyl Acetoacetate and a-Hydroxyacetophenone. Journal of Molecular Structure, 1225;
129086
Raczuk, E., B. Dmochowska, J. Samaszko-Fiertek, and J. Madaj (2022). Different Schiff Bases-Structure, Importance and Classification. Molecules, 27(3); 787
Sharma, P., D. Sharma, A. Sharma, N. Saini, R. Goyal, M. Ola, R. Chawla, and V. Thakur (2020). Hydrazone Comprising Compounds As Promising Anti-Infective Agents: Chemistry and Structure-Property Relationship. Materials Today Chemistry, 18; 100349
Vhanale, B. T., N. J. Deshmukh, and A. T. Shinde (2019). Synthesis, Characterization, Spectroscopic Studies and Biological Evaluation of Schiff Bases Derived from 1–Hydroxy2-Acetonapthanone. Heliyon, 5(11); 1–19
Zhang, D., W. Zhao, Z. Feng, Y. Wu, C. Huo, L. He, and W. Lu (2019). Preparation of Polymer–Rare Earth Complexes Based on Schiff-Base-Containing Salicylic Aldehyde Groups Attached to the Polymer and Their Fluorescence Emission Properties. e-Polymers, 19(1); 15–22
Adam, M. S. S., O. S. Abdel-Rahman, and M. M. Makhlouf (2023). Metal Ion Induced Changes in the Structure of Schiff Base Hydrazone Chelates and Their Reactivity Effect on Catalytic Benzyl Alcohol Oxidation and Biological Assays. Journal of Molecular Structure, 1272; 134164
Adejoro, I., F. Ojo, and S. Obafemi (2015). Corrosion Inhibition Potentials of Ampicillin for Mild Steel in Hydrochloric Acid Solution. Journal of Taibah University for Science, 9(2); 196–202
Al-Amiery, A. A., W. N. R. W. Isahak, and W. K. Al-Azzawi (2023). Corrosion Inhibitors: Natural and Synthetic Organic Inhibitors. Lubricants, 11(4); 174
Argyropoulos, V., S. C. Boyatzis, M. Giannoulaki, E. Guilminot, and A. Zacharopoulou (2021). Organic Green Corrosion Inhibitors Derived from Natural And/or Biological Sources for Conservation of Metals Cultural Heritage. Microorganisms in the Deterioration and Preservation of Cultural Heritage, 5; 341
Bouchtart, A., M. Rguiti, K. E. Mouaden, A. Abourine, R. Salghi, and L. Bazzi (2019). Copper Corrosion Inhibition in Acetic Acid by Some Heteroatom Organic: Case of 1-Phenyl-5-Mercapto Tetrazole. Applied Journal of Environmental Engineering Science, 5(2); 183–192
Charles, A., K. Sivaraj, and S. Thanikaikarasan (2020). Synthesis, Characterization and Corrosion Studies of Schiff Bases Derived from Pyrrole-2-Carbaldehyde. Materials Today: Proceedings, 33(7); 3135–3138
Chen, L., D. Lu, and Y. Zhang (2022). Organic Compounds As Corrosion Inhibitors for Carbon Steel in HCl Solution: A Comprehensive Review. Materials, 15(6); 2023
Deaf, H. K., E. Q. Jasim, H. Rafid, and K. Mohammed (2022). Synthesis, Corrosion Inhibition Study and DFT Calculation of Two New Azo Compounds. Egyptian Journal of Chemistry, 65(12); 481–492
Eduok, U. (2020). Theoretical Investigation of Molecular Properties of 5-Benzyl-6-Methyl Pyridazine-3-One and 5-Benzyl-6-Methyl Pyridazine-3-Thione and Their Potentials for Corrosion Inhibition for Steel. International Journal of Electrochemical Science, 15(12); 12080–12102
Elazabawy, O. E., O. A. El-Shamy, and N. E. El-Sattar (2023). Corrosion Inhibitory Characteristics, Thermodynamics, and Theoretical Studies of N-((2-Aminoethyl) Carbamothioyl) Acrylamide for Carbon Steel in 1 M HCl. Egyptian Journal of Petroleum, 32(3); 7–14
Erteeb, M., E. Ali-Shattle, S. Khalil, H. Berbash, and Z. Elshawi (2021). Computational Studies (DFT) and PM3 Theories on Thiophene Oligomers As Corrosion Inhibitors for Iron. Am J Chem, 11; 1–7
Gomathi, V. and R. Selvameena (2022). Synthesis, Structural Analysis and Antimicrobial Screening of Mn (II) Complexes of Schiff Bases. Journal of the Mexican Chemical Society, 66(1); 70–78
Guo, X., J. Wang, L. Huang, Y. Wang, L. Ma, D. Zhang, and L. Ma (2022). Corrosion Inhibition and Adsorption Process of 3-Amino-5-Mercapto-1, 2, 4-Triazole on Aluminium Alloy: Experimental and Theoretical Studies. Frontiers in Materials, 9; 874899
Hassan, A., M. S. Numin, K. Jumbri, K. E. Kee, N. Borhan, N. M. R. Nik Mohamed Daud, A. Mohammed Nor, M. F. Suhor, and R. Abdul Wahab (2023). Density Functional Theory Studies on New Possible Biobased Gemini Corrosion Inhibitors Derived from Fatty Hydrazide Derivatives. ACS Omega, 8(26); 23945–23952
Jabeen, M. (2022). A Comprehensive Review on Analytical Applications of Hydrazone Derivatives. Journal of the Turkish Chemical Society Section A: Chemistry, 9(3); 663–698
Jasim, E. Q., E. A. Alasadi, R. H. Fayadh, and M. A. Muhamman-Ali (2020). Synthesis and Antibacterial Evaluation of Some Azo-Schiff Base Ligands and Estimation the Cadmium Metal by Complexation. Systematic Reviews in Pharmacy, 11(6); 677–687
Jasim, E. Q., M. A. Ma, and R. H. Fayadh (2017). Synthesis and Characterization of Some Thiadiazole Compounds as New Corrosion Inhibitors for Mild Steel in Cooling Water. Asian Journal of Chemistry, 29(11); 2361–2365
Jasim, E. Q., M. A. Muhammad-Ali, and A. Almakki (2023). Synthesis, Characterization, and Antibacterial Activity of Some Mesalazine Derivatives. Science and Technology Indonesia, 8(3); 338–343
Kuraimid, Z. K., D. S. Abid, and A. E.-A. S. Fouda (2023). Synthesis and Characterization of a Novel Quaternary Ammonium Salt as a Corrosion Inhibitor for Oil-Well Acidizing Processes. ACS Omega, 8(30); 27079–27091
Lgaz, H., A. Chaouiki, M. R. Albayati, R. Salghi, Y. El Aoufir, I. H. Ali, M. I. Khan, S. K. Mohamed, and I.-M. Chung (2019). Synthesis and Evaluation of Some New Hydrazones As Corrosion Inhibitors for Mild Steel in Acidic Media. Research on Chemical Intermediates, 45; 2269–2286
Maniak, H., M. Talma, and M. Giurg (2021). Inhibitory Potential of New Phenolic Hydrazide Hydrazones with a Decoy Substrate Fragment Towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies. International Journal of Molecular Sciences, 22(22); 12307
Mazlan, N., K. Jumbri, M. A. Kassim, R. A. Wahab, and M. B. A. Rahman (2022). Density Functional Theory and Molecular Dynamics Simulation Studies of Bio-Based Fatty Hydrazide-Corrosion Inhibitors on Fe (1 1 0) in Acidic Media. Journal of Molecular Liquids, 347; 118321
Muhammad, A. A., T. A. Nyijime, and A. S. Muhammad (2020). Density Functional Theory and Molecular Dynamic Simulation Studies on the Corrosion Inhibition of Some Thiosemicarbazide Derivatives on Aluminum Metal. Journal of Applied Surfaces and Interfaces, 8(1-3); 7–14
Muhammad-Ali, M. A., E. Q. Jasim, and A. H. Al-Saadoon (2023). Synthesis, Antibacterial Evaluation, and Docking Studies of Some Azo Compounds and Schiff Bases Derived from Sulfonamide. Journal of Medicinal and Chemical Sciences, 6(9); 2128–2139
Njong, R. N., B. N. Ndosiri, E. N. Nfor, and O. E. Offiong (2018). Corrosion Inhibitory Studies of Novel Schiff Bases Derived from Hydralazine Hydrochloride on Mild Steel in Acidic Media. Open Journal of Physical Chemistry, 8(1); 15–32
Obot, I., A. A. Bahraq, and A. H. Alamri (2022). Density Functional Theory and Molecular Dynamics Simulation of the Corrosive Particle Diffusion in Pyrimidine and Its Derivatives Films. Computational Materials Science, 210; 111428
Oukhrib, R., Y. Abdellaoui, A. Berisha, H. Abou Oualid, J. Halili, K. Jusufi, M. Ait El Had, H. Bourzi, S. El Issami, and F. A. Asmary (2021). DFT, Monte Carlo and Molecular Dynamics Simulations for the Prediction of Corrosion Inhibition Efficiency of Novel Pyrazolylnucleosides on Cu (111) Surface in Acidic Media. Scientific Reports, 11(1); 3771
Oyeneyin, O. E., N. D. Ojo, N. Ipinloju, E. B. Agbaffa, and A. V. Emmanuel (2022). Investigation of the Corrosion Inhibition Potentials of Some 2-(4-(substituted) Arylidene)-1H-Indene-1, 3-Dione Derivatives: Density Functional Theory and Molecular Dynamics Simulation. Beni-Suef University Journal of Basic and Applied Sciences, 11(1); 1–14
Packialakshmi, P., P. Gobinath, D. Ali, S. Alarifi, R. Gurusamy, A. Idhayadhulla, and R. Surendrakumar (2022). New Chitosan Polymer Scaffold Schiff Bases As Potential Cytotoxic Activity: Synthesis, Molecular Docking, and Physiochemical Characterization. Frontiers in Chemistry, 9; 796599
Parvarinezhad, S. and M. Salehi (2021). Synthesis, Characterization, Anti-Proliferative Activity and Chemistry Computation of DFT Theoretical Methods of Hydrazine-Based Schiff Bases Derived from Methyl Acetoacetate and a-Hydroxyacetophenone. Journal of Molecular Structure, 1225;
129086
Raczuk, E., B. Dmochowska, J. Samaszko-Fiertek, and J. Madaj (2022). Different Schiff Bases-Structure, Importance and Classification. Molecules, 27(3); 787
Sharma, P., D. Sharma, A. Sharma, N. Saini, R. Goyal, M. Ola, R. Chawla, and V. Thakur (2020). Hydrazone Comprising Compounds As Promising Anti-Infective Agents: Chemistry and Structure-Property Relationship. Materials Today Chemistry, 18; 100349
Vhanale, B. T., N. J. Deshmukh, and A. T. Shinde (2019). Synthesis, Characterization, Spectroscopic Studies and Biological Evaluation of Schiff Bases Derived from 1–Hydroxy2-Acetonapthanone. Heliyon, 5(11); 1–19
Zhang, D., W. Zhao, Z. Feng, Y. Wu, C. Huo, L. He, and W. Lu (2019). Preparation of Polymer–Rare Earth Complexes Based on Schiff-Base-Containing Salicylic Aldehyde Groups Attached to the Polymer and Their Fluorescence Emission Properties. e-Polymers, 19(1); 15–22
Authors
Abood, H. S., Jasim, E. Q., & Muhammad-Ali, M. A. (2024). Synthesis, Corrosion Inhibition Efficiency in Acidic Media, and Quantum Chemical Studies of Some Hydrazine Derivatives. Science and Technology Indonesia, 9(1), 137–147. https://doi.org/10.26554/sti.2024.9.1.137-147
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