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Two Novel Benzodiazepines as Corrosion Inhibitors for Carbon Steel in Hydrochloric Acid: Experimental and Computational Studies

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Abstract

Two new benzodiazepine derivatives namely, 1-ethyl-4-(2-oxopropylidene)-1,2,4,5-tetrahydro-2H-1,5-benzodiazepine-2-one (BZD-1) and 1-octyl-4-(2-oxopropylidene)-1,2,4,5-tetrahydro-2H-1,5-benzodiazepine-2-one (BZD-2) have been synthesized and used as corrosion inhibitors for carbon steel in acidic solution (1 M HCl). Corrosion inhibition evaluation was performed using weight loss, electrochemical techniques [potentiodynamic polarization (PDP) and electrochemical impedance spectroscopy (EIS)], quantum chemical calculations, and molecular dynamic (MD) simulations. The results showed that both compounds are good corrosion inhibitors for carbon steel in 1 M HCl medium; their inhibition efficiency increased with inhibitor concentration. In addition, the results obtained from above methods reveal that BDZ-2 is an excellent inhibitor. It gives a maximum inhibition efficiency of 96.63% at 10−3 M and inhibits corrosion by adsorbing at the carbon steel surface. EIS measurements showed that the charge transfer resistance increases, whereas the double-layer capacitance decreases with the inhibitor concentration. Polarization studies showed that BDZ-1 and BDZ-2 are mixed type. The tested inhibitors have been adsorbed on the carbon steel surface according to Langmuir isotherm adsorption model. The experimental results are in reasonably close agreement with quantum chemical parameters calculated at DFT/B3LYB/3-21G and the molecular dynamic simulations results.

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References

  1. Lagrenee M, Mernari B, Bouanis M et al (2002) Study of the mechanism and inhibiting efficiency of 3, 5-bis (4-methylthiophenyl)-4H-1, 2, 4-triazole on mild steel corrosion in acidic media. Corros Sci 44:573–588

    Article  CAS  Google Scholar 

  2. Torres VV, Amado RS, De Sá CF et al (2011) Inhibitory action of aqueous coffee ground extracts on the corrosion of carbon steel in HCl solution. Corros Sci 53:2385–2392

    Article  CAS  Google Scholar 

  3. Tebbji K, Faska N, Tounsi A et al (2007) The effect of some lactones as inhibitors for the corrosion of mild steel in 1 M hydrochloric acid. Mater Chem Phys 106:260–267

    Article  CAS  Google Scholar 

  4. Yurt A, Bütün V, Duran B (2007) Effect of the molecular weight and structure of some novel water-soluble triblock copolymers on the electrochemical behaviour of mild steel. Mater Chem Phys 105:114–121

    Article  CAS  Google Scholar 

  5. Bouklah M, Ouassini A, Hammouti B, El Idrissi A (2005) Corrosion inhibition of steel in 0.5 M H2SO4 by [(2-pyridin-4-ylethyl) thio] acetic acid. Appl Surf Sci 250:50–56

    Article  CAS  Google Scholar 

  6. Tang Y, Yang X, Yang W et al (2010) Experimental and molecular dynamics studies on corrosion inhibition of mild steel by 2-amino-5-phenyl-1, 3, 4-thiadiazole. Corros Sci 52:242–249

    Article  CAS  Google Scholar 

  7. Kumar R, Joshi YC (2007) Synthesis, spectral studies and biological activity of 3H-1, 5-benzodiazepine derivatives. Arkivoc 13:142–149

    Google Scholar 

  8. Kanyonga PM, Zellou A, Essassi M, Cherrah Y (2010) Synthèse et évaluation de l’activité pharmacologique de la 4-phényl-1, 5-benzodiazépin-2-one et ses dérivés. Int J Biol Chem Sci. https://doi.org/10.4314/ijbcs.v4i1.54223

    Article  Google Scholar 

  9. Ahabchane NH, Keïta A, Essassi EM (1999) Synthèse des 1-pyrazolyl, isoxazolyl et 1, 2, 3-triazolylméthyl-1, 5-benzodiazépines par cycloaddition dipolaire-1, 3. Comptes Rendus Acad Sci-Ser IIC-Chem 2:519–523

    CAS  Google Scholar 

  10. Chen Y, Le V, Xu X et al (2014) Discovery of novel 1, 5-benzodiazepine-2, 4-dione derivatives as potential anticancer agents. Bioorg Med Chem Lett 24:3948–3951

    Article  CAS  Google Scholar 

  11. Nicholson AN, Stone BM, Clarke CH (1977) Effect of the 1, 5-benzodiazepines, clobazam and triflubazam, on sleep in man. Br J Clin Pharmacol 4:567–572

    Article  CAS  Google Scholar 

  12. Niouri W, Zerga B, Sfaira M et al (2012) Substitution effect of two oxygen atoms by sulphur atoms in new synthesized benzodiazepine molecules towards mild steel corrosion inhibition in hydrochloric acid. Int J Electrochem Sci 7:10190–10204

    CAS  Google Scholar 

  13. Niouri W, Zerga B, Sfaira M et al (2014) Electrochemical and chemical studies of some benzodiazepine molecules as corrosion inhibitors for mild steel in 1 M HCl. Int J Electrochem Sci 9:8283–8298

    CAS  Google Scholar 

  14. Laabaissi T, Bouassiria M, Oudda H et al (2016) Adsorption and corrosion inhibition effect of benzodiazepine derivative on carbon steel in 2.0 MH3po4 medium. J Mater Environ Sci 7:1538–1548

    CAS  Google Scholar 

  15. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA, Gaussian 03, Revision C.02,

  16. Koopmans T (1934) The classification of wave functions and eigen-values to the single electrons of an atom. Physica 1:104–113

    Article  Google Scholar 

  17. Pearson RG (1988) Absolute electronegativity and hardness: application to inorganic chemistry. Inorg Chem 27:734–740

    Article  CAS  Google Scholar 

  18. Guo L, Obot IB, Zheng X et al (2017) Theoretical insight into an empirical rule about organic corrosion inhibitors containing nitrogen, oxygen, and sulfur atoms. Appl Surf Sci 406:301–306. https://doi.org/10.1016/j.apsusc.2017.02.134

    Article  CAS  Google Scholar 

  19. BIOVIA DS (2016) BIOVIA materials studio. San Diego, CA

  20. Sun H (1998) COMPASS: an ab initio force-field optimized for condensed-phase applications overview with details on alkane and benzene compounds. J Phys Chem B 102:7338–7364

    Article  CAS  Google Scholar 

  21. Gupta NK, Verma C, Quraishi MA, Mukherjee AK (2016) Schiff’s bases derived from L-lysine and aromatic aldehydes as green corrosion inhibitors for mild steel: experimental and theoretical studies. J Mol Liq 215:47–57

    Article  CAS  Google Scholar 

  22. Liu FG, Du M, Zhang J, Qiu M (2009) Electrochemical behavior of Q235 steel in saltwater saturated with carbon dioxide based on new imidazoline derivative inhibitor. Corros Sci 51:102–109

    Article  Google Scholar 

  23. Popova A, Sokolova E, Raicheva S, Christov M (2003) AC and DC study of the temperature effect on mild steel corrosion in acid media in the presence of benzimidazole derivatives. Corros Sci 45:33–58

    Article  Google Scholar 

  24. Zhang D, Tang Y, Qi S et al (2016) The inhibition performance of long-chain alkyl-substituted benzimidazole derivatives for corrosion of mild steel in HCl. Corros Sci 102:517–522. https://doi.org/10.1016/j.corsci.2015.10.002

    Article  CAS  Google Scholar 

  25. Zucchi F, Trabanelli G, Brunoro G (1992) The influence of the chromium content on the inhibitive efficiency of some organic compounds. Corros Sci 33:1135–1139

    Article  CAS  Google Scholar 

  26. Ashassi-Sorkhabi H, Shaabani B, Seifzadeh D (2005) Corrosion inhibition of mild steel by some Schiff base compounds in hydrochloric acid. Appl Surf Sci 239:154–164

    Article  CAS  Google Scholar 

  27. Roy P, Karfa P, Adhikari U, Sukul D (2014) Corrosion inhibition of mild steel in acidic medium by polyacrylamide grafted Guar gum with various grafting percentage: effect of intramolecular synergism. Corros Sci 88:246–253

    Article  CAS  Google Scholar 

  28. Verma CB, Quraishi MA, Singh A (2015) 2-Aminobenzene-1, 3-dicarbonitriles as green corrosion inhibitor for mild steel in 1 M HCl: electrochemical, thermodynamic, surface and quantum chemical investigation. J Taiwan Inst Chem Eng 49:229–239

    Article  CAS  Google Scholar 

  29. Tawfik SM (2016) Ionic liquids based gemini cationic surfactants as corrosion inhibitors for carbon steel in hydrochloric acid solution. J Mol Liq 216:624–635

    Article  CAS  Google Scholar 

  30. Kowsari E, Payami M, Amini R et al (2014) Task-specific ionic liquid as a new green inhibitor of mild steel corrosion. Appl Surf Sci 289:478–486

    Article  CAS  Google Scholar 

  31. Alinejad S, Naderi R, Mahdavian M (2017) Effect of inhibition synergism of zinc chloride and 2-mercaptobenzoxzole on protective performance of an ecofriendly silane coating on mild steel. J Ind Eng Chem 48:88–98

    Article  CAS  Google Scholar 

  32. Zhao J, Duan H, Jiang R (2015) Synergistic corrosion inhibition effect of quinoline quaternary ammonium salt and Gemini surfactant in H2S and CO2 saturated brine solution. Corros Sci 91:108–119

    Article  CAS  Google Scholar 

  33. Verma C, Quraishi MA, Olasunkanmi LO, Ebenso EE (2015) L-Proline-promoted synthesis of 2-amino-4-arylquinoline-3-carbonitriles as sustainable corrosion inhibitors for mild steel in 1 M HCl: experimental and computational studies. RSC Adv 5:85417–85430

    Article  CAS  Google Scholar 

  34. Lei X, Wang H, Feng Y et al (2015) Synthesis, evaluation and thermodynamics of a 1H-benzo-imidazole phenanthroline derivative as a novel inhibitor for mild steel against acidic corrosion. RSC Adv 5:99084–99094

    Article  CAS  Google Scholar 

  35. Zhang K, Xu B, Yang W et al (2015) Halogen-substituted imidazoline derivatives as corrosion inhibitors for mild steel in hydrochloric acid solution. Corros Sci 90:284–295

    Article  CAS  Google Scholar 

  36. Bentiss F, Lebrini M, Vezin H, Lagrenée M (2004) Experimental and theoretical study of 3-pyridyl-substituted 1, 2, 4-thiadiazole and 1, 3, 4-thiadiazole as corrosion inhibitors of mild steel in acidic media. Mater Chem Phys 87:18–23

    Article  CAS  Google Scholar 

  37. Guadalupe HJ, Garcia-Ochoa E, Maldonado-Rivas PJ et al (2011) A combined electrochemical and theoretical study of N,N′-bis (benzimidazole-2yl-ethyl)-1, 2-diaminoethane as a new corrosion inhibitor for carbon steel surface. J Electroanal Chem 655:164–172

    Article  CAS  Google Scholar 

  38. Verma C, Quraishi MA, Ebenso EE et al (2016) 3-Amino alkylated indoles as corrosion inhibitors for mild steel in 1 M HCl: experimental and theoretical studies. J Mol Liq 219:647–660

    Article  CAS  Google Scholar 

  39. de Souza FS, Spinelli A (2009) Caffeic acid as a green corrosion inhibitor for mild steel. Corros Sci 51:642–649

    Article  Google Scholar 

  40. Chidiebere MA, Ogukwe CE, Oguzie KL et al (2012) Corrosion inhibition and adsorption behavior of Punica granatum extract on mild steel in acidic environments: experimental and theoretical studies. Ind Eng Chem Res 51:668–677

    Article  CAS  Google Scholar 

  41. Popova A, Christov M, Raicheva S, Sokolova E (2004) Adsorption and inhibitive properties of benzimidazole derivatives in acid mild steel corrosion. Corros Sci 46:1333–1350

    Article  CAS  Google Scholar 

  42. Goulart CM, Esteves-Souza A, Martinez-Huitle CA et al (2013) Experimental and theoretical evaluation of semicarbazones and thiosemicarbazones as organic corrosion inhibitors. Corros Sci 67:281–291

    Article  CAS  Google Scholar 

  43. Amin MA, Ibrahim MM (2011) Corrosion and corrosion control of mild steel in concentrated H2SO4 solutions by a newly synthesized glycine derivative. Corros Sci 53:873–885

    Article  CAS  Google Scholar 

  44. Danaee I, Ghasemi O, Rashed GR et al (2013) Effect of hydroxyl group position on adsorption behavior and corrosion inhibition of hydroxybenzaldehyde Schiff bases: electrochemical and quantum calculations. J Mol Struct 1035:247–259

    Article  CAS  Google Scholar 

  45. Obot IB, Kaya S, Kaya C, Tüzün B (2016) Density functional theory (DFT) modeling and Monte Carlo simulation assessment of inhibition performance of some carbohydrazide Schiff bases for steel corrosion. Physica E 80:82–90

    Article  CAS  Google Scholar 

  46. Deng S, Li X, Fu H (2011) Acid violet 6B as a novel corrosion inhibitor for cold rolled steel in hydrochloric acid solution. Corros Sci 53:760–768

    Article  CAS  Google Scholar 

  47. Khalil N (2003) Quantum chemical approach of corrosion inhibition. Electrochim Acta 48:2635–2640

    Article  CAS  Google Scholar 

  48. Li L, Zhang X, Lei J et al (2012) Adsorption and corrosion inhibition of Osmanthus fragran leaves extract on carbon steel. Corros Sci 63:82–90

    Article  CAS  Google Scholar 

  49. Li X, Deng S, Fu H, Li T (2009) Adsorption and inhibition effect of 6-benzylaminopurine on cold rolled steel in 1.0 M HCl. Electrochim Acta 54:4089–4098

    Article  CAS  Google Scholar 

  50. Daoud D, Douadi T, Hamani H et al (2015) Corrosion inhibition of mild steel by two new S-heterocyclic compounds in 1 M HCl: experimental and computational study. Corros Sci 94:21–37

    Article  CAS  Google Scholar 

  51. Xie S-W, Liu Z, Han G-C et al (2015) Molecular dynamics simulation of inhibition mechanism of 3, 5-dibromo salicylaldehyde Schiff’s base. Comput Theor Chem 1063:50–62

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Nanotechnology, Materials & Environment, Faculty of Sciences, University Mohammed V, Rabat, Morocco

    Yasmina El Aoufir & Abdellah Guenbour

  2. Laboratory separation processes, Faculty of Science, University Ibn Tofail, PO Box 242, Kenitra, Morocco

    Yasmina El Aoufir, Abdelkarim Chaouiki, Hassane Lgaz & Hassan Oudda

  3. Laboratoire de Chimie Organique Heterocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Université Mohammed V, Faculté des Sciences, Rabat, Morocco

    Jihad Sebhaoui & El Mokhtar Essassi

  4. Laboratory of Environmental Engineering and Biotechnology, ENSA, University Ibn Zohr, PO Box 1136, 80000, Agadir, Morocco

    Abdelkarim Chaouiki & Rachid Salghi

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  1. Yasmina El Aoufir
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  2. Jihad Sebhaoui
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Correspondence to Rachid Salghi.

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El Aoufir, Y., Sebhaoui, J., Chaouiki, A. et al. Two Novel Benzodiazepines as Corrosion Inhibitors for Carbon Steel in Hydrochloric Acid: Experimental and Computational Studies. J Bio Tribo Corros 4, 54 (2018). https://doi.org/10.1007/s40735-018-0169-5

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  • DOI: https://doi.org/10.1007/s40735-018-0169-5

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