Citation: SHI Hong, XU Bin, ZHU Hong-Jun. Electrochemical and Theoretical Studies of 1-Alkyl-2-substituted Benzimidazoles as Corrosion Inhibitors for Carbon Steel Surface in HCl Medium[J]. Chinese Journal of Structural Chemistry, ;2016, 35(12): 1829-1839. doi: 10.14102/j.cnki.0254-5861.2011-1099 shu

Electrochemical and Theoretical Studies of 1-Alkyl-2-substituted Benzimidazoles as Corrosion Inhibitors for Carbon Steel Surface in HCl Medium

SHI Hong ^a,*,, ,
XU Bin ^b ,
ZHU Hong-Jun ^b

a.
School of Electrical and Mechanical Engineering, Jiangsu Vocational College of Information Technology, Wuxi 214153, China
b.
School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211800, China

Corresponding author: SHI Hong, shishi722@sina.com
Received Date: 25 December 2015
Accepted Date: 8 September 2016

Fund Project: Natural Science Foundation of Jiangsu Province BK20150123

Figures(4)

The inhibition efficiencies of newly synthesized four 1-alkyl-2-substituted benzimidazole compounds (a~d) have been studied for the corrosion of carbon steel in 1.0 M HCl by using potentiodynamic polarization measurement. The four inhibitors act as mixed-type inhibitors, which mainly inhibit cathodes. The inhibition efficiency of these compounds enhanced when the concentration of the inhibitors increased. A theoretical study of the corrosion inhibition efficiency of these compounds was carried out by using the B3LYP level with the 6-31+G^* basis set. Considering the solvent effect, the IEFPCM model was selected. Furthermore, the adsorption energies of the inhibitors with the iron (001) surface were studied by using molecular dynamic (MD) simulations. The theoretical results show that these inhibitors all exhibit several adsorption active-centers. Meanwhile, the MD simulations indicate that the adsorption occurs mostly through benzene ring and the lone pair electrons of the nitro atoms. These results demonstrated that the theoretical studies and MD simulations are reliable and promising methods for analyzing the inhibition efficiency of organic inhibitors.
- benzimidazole,
- electrochemical techniques,
- inhibitor,
- DFT,
- molecular dynamic
1. [1]
  Abdallah, M. Corrosion behavior of 304 stainless steel in sulphuric acid solutions and its inhibition by some substituted pyrazolones[J]. Mater. Chem. Phys, 2003,82:786-792. doi: 10.1016/S0254-0584(03)00367-5
2. [2]
  Düdükcü M, Yazici B, Erbil M. The effect of indole on the corrosion behavior of stainless steel[J]. Mater. Chem. Phys, 2004,87:138-141. doi: 10.1016/j.matchemphys.2004.05.043
3. [3]
  Ismail A. A, Sanad S. H, El-Meligi A. A. Inhibiting effect of indole and some of its derivatives on corrosion of C-steel in HCl[J]. J. Mater. Sci. Technol, 2000,16:397-400.
4. [4]
  Tang Y. M, Zhang F, Hu S. X, Cao Z. Y, Wu Z. L, Jing W. H. Novel benzimidazole derivatives as corrosion inhibitors of mild steel in the acidic media[J]. Part I: gravimetric, electrochemical, SEM and XPS studies. Corros. Sci, 2013,74:271-282.
5. [5]
  Yuce A. O, Kardas G. Adsorption and inhibition effect of 2-thiohydantoin on mild steel corrosion in 0.1M HCl[J]. Corros. Sci, 2012,58:86-94. doi: 10.1016/j.corsci.2012.01.013
6. [6]
  Bentiss F, Jama C, Mernari B. Electrochemical and XPS studies of the corrosion inhibition of carbon steel in hydrochloric acid pickling solutions by 3,5-bis(2-thienylmethyl)-4-amino-1,2,4-triazole[J]. Corros. Sci, 2013,75:123-133. doi: 10.1016/j.corsci.2013.05.023
7. [7]
  Sastry V. S. Corrosion Inhibitors Principles and Applications[J]. John Wiley & Sons: New York, 1998:p551-555.
8. [8]
  Jones D. A. Principles and prevention of corrosion, seconded[J]. Prentice-Hall Inc: New Jersey, 1996:p659-p664.
9. [9]
  Adnani E. I. Z, Mcharfi M, Sfaira M, Benjelloun A. T. Investigation of newly pyridazine derivatives as corrosion inhibitors in molar hydrochloric acid[J]. Part III: computational calculations. Int. J. Electrochem. Sci, 2012,75:3982-3996.
10. [10]
  Zhang F, Tang Y. M, Cao Z. Y, Jing W. H, Wu Z. L, Chen Y. Z. Performance and theoretical study on corrosion inhibition of 2-(4-pyridyl)-benzimidazole for mild steel in hydrochloric acid[J]. Corro. Sci, 2012,61:1-9. doi: 10.1016/j.corsci.2012.03.045
11. [11]
  Bentiss F, Traisnel M, Gengembre L, Lagrenée M. A new triazole derivative as inhibitor of the acid corrosion of mild steel: electrochemical studies, weight loss determination, SEM and XPS[J]. Appl. Surf. Sci, 1999,152:237-249. doi: 10.1016/S0169-4332(99)00322-0
12. [12]
  Granese S. L, Rosales B. M, Oviedo C; Zerbino J. O. The inhibition action of heterocyclic nitrogen organic compounds on Fe and steel in HCl media[J]. Corros. Sci, 1992,22:1439-1453.
13. [13]
  Quraishi , M. A. 2-Amino-3,5-dicarbonitrile-6-thio-pyridines: new and effective corrosion inhibitors for mild steel in 1 M HCl[J]. Ind. Eng. Chem. Res, 2014,53:2851-2859. doi: 10.1021/ie401633y
14. [14]
  Tang Y. M, Yang X. Y, Yang W. Z, Wan R, Chen Y. Z, Yin X. S. A preliminary investigation of corrosion inhibition of mild steel in 0.5 M H2SO4 by 2-amino-5-(n-pyridyl)-1,3,4-thiadiazole: polarization, EIS and molecular dynamics simulations[J]. Corro. Sci, 2010,52:1801-1808. doi: 10.1016/j.corsci.2010.01.028
15. [15]
  Kosari A, Moayed M. H, Davoodi A, Parvizi R, Momeni M, Eshghi H. Electrochemical and quantum chemical assessment of two organic compounds from pyridine derivatives as corrosion inhibitors for mild steel in HCl solution under stagnant condition and hydrodynamic flow[J]. Corro. Sci, 2014,78:138-150. doi: 10.1016/j.corsci.2013.09.009
16. [16]
  Reit Y, D?ner A, Do?an T, Dehri ?. Experimental studies of 2-yridinecarbonitrile as corrosion inhibitor for mild steel in hydrochloric acid solution[J]. Corro. Sci, 2014,82:125-132. doi: 10.1016/j.corsci.2014.01.008
17. [17]
  Mert B. D, Yüce A. O, Kardas G. Inhibition effect of 2-amino-4-methylpyridine on mild steel corrosion: experimental and theoretical investigation[J]. Corro. Sci, 2014,85:287-295. doi: 10.1016/j.corsci.2014.04.032
18. [18]
  Ozdemir I, Temelli N, Gunal S, Demir S. Gold(I) complexes of N-heterocyclic carbene ligands containing benzimidazole: synthesis and antimicrobial activity[J]. Molecules, 2010,15:2203-2210. doi: 10.3390/molecules15042203
19. [19]
  Alka S; Vijay L, Kamaldeep P. Original article: purine-benzimidazole hybrids: synthesis, single crystal determination and in vitro evaluation of antitumor activities[J]. Eur. J. Med. Chem, 2015,93:414-422. doi: 10.1016/j.ejmech.2015.02.036
20. [20]
  Prapthi B, Lakshmi K, Vijaya N. Antidiabetic effect of 2 nitro benzimidazole in alloxan induced diabetic rats[J]. International Journal of Basic & Clinical Pharmacology, 2013,6:814-818.
21. [21]
  Sekar V. K, Raj S. M, Kumar C. S. Original article: synthesis, characterization and evaluation of N-mannich bases of 2-substituted benzimidazole derivatives[J]. Journal of Young Pharmacists, 2013,5:154-159. doi: 10.1016/j.jyp.2013.11.004
22. [22]
  Lindsay S, Lo S. K, Maguire O. R, Bill E, Probert M. R, Sproules S. Syntheses and electronic structure of bimetallic complexes containing a flexible redox-active bridging ligand[J]. Inorg. Chem, 2013,52:898-909. doi: 10.1021/ic302087f
23. [23]
  Wa, L. Evaluation of 2-mercaptobenzimidazole as corrosion inhibitor for mild steel in phosphoric acid[J]. Corros. Sci, 2001,43:2281-2289. doi: 10.1016/S0010-938X(01)00036-1
24. [24]
  Shi H, Wu T, Jiang P, Zhu H. J. Series of novel blue light-emitting 1-arkyl-2-substituted benzimidazoles: synthesis, characterization, optical properties and theoretical calculation[J]. Asian J. Chem, 2013,25:4481-4486.
25. [25]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; 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, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth G. A, Salvador P, Dannenberg J. J, Zakrzewski V. G, Dapprich S, Daniels A. D, Strain M. C, FarkasO, Malick D. K, Rabuck A. D, Raghavachari K, Foresman J. B, Ortiz J. V, Cui Q, Baboul A. G, Clifford S, Cioslowski J, Stefanov B. B, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin R. L, Fox D. J, Keith T, Al-Laham M. A, Peng C. Y, Nanayakkara A, Challacombe M, Gill P. M. W, Johnson B, Chen W, Wong M. W, Gonzalez C, Pople J. A.Gaussian, Inc., Pittsburgh PA, 2003, Gaussian 03, Revision B.01.
26. [26]
  Wang W. H, Li Z, Sun Q, Du A. J, Li Y. L. ; Wang J, Bi S. W, Li P. Insights into the nature of the coupling interactions between uracil corrosion inhibitors and copper: A DFT and molecular dynamics study[J]. Corros. Sci, 2012,61:101-110. doi: 10.1016/j.corsci.2012.04.025
27. [27]
  Fukui, K. Theory of orientation and stereoselection. Springer-Verlag: New York, 1975, p134-146.
28. [28]
  Ge, G. The use of quantum chemical methods in corrosion inhibitor studies[J]. Corros. Sci, 2008,50:2981-2992. doi: 10.1016/j.corsci.2008.08.043
29. [29]
  Bostan R, Varvara S, Gaina L, Muresan L. M. Evaluation of some phenothiazine derivatives as corrosion inhibitors for bronze in weakly acidic solution[J]. Corros. Sci, 2002,63:275-286.
30. [30]
  Mert B. D, Yuce A. O, KardaA G, Yazici B. Inhibition effect of 2-amino-4-methylpyridine on mild steel corrosion: experimental and theoretical investigation[J]. Corros. Sci, 2014,85:287-295. doi: 10.1016/j.corsci.2014.04.032
31. [31]
  Obi-Egbedi N. O, Obot I. B. Inhibitive properties, thermodynamic and quantum chemical studies of alloxazine on mild steel corrosion in H2SO4[J]. Corros. Sci, 2011,53:263-275. doi: 10.1016/j.corsci.2010.09.020
32. [32]
  Obot I. B, Gasem Z. M. Theoretical evaluation of corrosion inhibition performance of some pyrazine derivatives[J]. Corros. Sci, 2014,83:359-366. doi: 10.1016/j.corsci.2014.03.008
33. [33]
  Cao Z. Y, Tang Y. M, Cang H, Xu J. Q, Lu G, Jing W. H. Novel benzimidazole derivatives as corrosion inhibitors of mild steel in the acidic media[J]. Part Ⅱ: theoretical studies. Corros. Sci, 2014,83:292-298.
34. [34]
  Xu B, Liu Y, Yin X. S, Yang W. Z, Chen Y. Z. Experimental and theoretical study of corrosion inhibition of 3-pyridinecarbozalde thiosemicarbazone for mild steel in hydrochloric acid[J]. Corros. Sci, 2013,74:206-213. doi: 10.1016/j.corsci.2013.04.044
35. [35]
  Zhang K. G, Xu B, Yang W. Z, Yin X. S, Liu Y, Chen Y. Z. Halogen-substituted imidazoline derivatives as corrosion inhibitors for mild steel in hydrochloric acid solution[J]. Corros. Sci, 2015,90:284-295. doi: 10.1016/j.corsci.2014.10.032
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