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

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
1. [1]
  Shahla Hamedani , Hossein Aghaie . Molecular Structure and Theoretical Thermodynamic Study of Folic Acid Based on the Computational Approach. Chinese Journal of Structural Chemistry, 2015, 34(9): 1307-1316. doi: 10.14102/j.cnki.0254-5861.2011-0688
2. [2]
  Song Qing WANG , Xiu Jie LIU , Zhi Ming YI , Kang ZHAO . Design and Synthesis of New Arylsulfonamide and Arylamide Derivatives for the Platelet Aggression Inhibitor. Chinese Chemical Letters, 2003, 14(6): 581-584.
3. [3]
  Min DU , Rong Jie GAO , Ping GONG , Qing Zhang WANG . The New-generation of Green Surfactant (Alkylpolyglucoside) as an Inhibitor to the Corrosion of 907 Steel in Seawater. Chinese Chemical Letters, 2004, 15(8): 985-988.
4. [4]
  Xi Rong HUANG , Wen Juan ZHANG , Shu Hua HAN , Gui Ying XU . A Highly Sensitive Kinetic Spectrophotometric System and Its Analytical Potential for Chromatographic Detection of Metal Ions. Chinese Chemical Letters, 1999, 10(1): 51-54.
5. [5]
  Shahl Hamedani , Shahram Moradi , Hossein Aghaie . Adsorption of Folic Acid on the Single-walled Carbon Nanotubes: AIM and NBO Analyses via DFT. Chinese Journal of Structural Chemistry, 2015, 34(8): 1161-1169. doi: 10.14102/j.cnki.0254-5861.2011-0677
6. [6]
  GUO Rui , LIU Guang , ZHANG Yang , LI Chao-Yang , QI Jing-Yu , LIU Xuan-Wen , SU Na . Synthesis, Crystal Structure, Fluorescent Property and DFT Study of a Novel 1D Polymer[Zn(HMICD)(bpy)]_n·2nH₂O. Chinese Journal of Structural Chemistry, 2016, 35(9): 1420-1426. doi: 10.14102/j.cnki.0254-5861.2011-1140
7. [7]
  PAN Rong-Kai , LI Guo-Bi , LIU Sheng-Gui , YANG Gui-Zhen , ZHOU Xiao-Ping , CHEN Xiao-Ying . Synthesis, Crystal Structure and Redox Property of a Copper(II) Complex Based on 1,1-Bis(1H-benzoimidazol-2-ylmethyl)cyclohexane. Chinese Journal of Structural Chemistry, 2016, 35(3): 348-354. doi: 10.14102/j.cnki.0254-5861.2011-0893
8. [8]
  XIA Li , ZHU Yu , WANG Yan-Mei , LIU Pan , XIE Ji-Min . Syntheses, Structures, Fluorescence and Heterogeneous Catalysis of Coordination Polymers with 4-Benzoimidazol-1-yl-methyl Benzoic Acid and 2,2'-Dipyridine. Chinese Journal of Structural Chemistry, 2016, 35(4): 577-585. doi: 10.14102/j.cnki.0254-5861.2011-0909
9. [9]
  SU Wen-Yi , LI Guo-Bi , PAN Rong-Kai , TANG Fei-Qiong , ZHONG Ling , LIU Sheng-Gui . Synthesis, Crystal Structure and Luminescent Property of Cadmium Complex Based on 2-(2-(1Hbenzo[d]imidazol-2-yl)benzyl)-1H-benzo[d]-imidazole. Chinese Journal of Structural Chemistry, 2014, 33(6): 909-914.
10. [10]
  WU Qi-Ting , WU Li-Bin , LI Guo-Bi , LIU Sheng-Gui , PAN Rong-Kai , SU Wen-Yi , HUANG Qian-Wen . Synthesis, Crystal Structure and Luminescent Property of a Dinuclear Cadmium Complex Based on 1,2,3,4-Tetra(1H-benzo[d]imidazol-2-yl)butane. Chinese Journal of Structural Chemistry, 2015, 34(2): 260-266. doi: 10.14102/j.cnki.0254-5861.2011-0464
11. [11]
  Feng Mei NIE , Yan Mei LI , Yu Fen ZHAO , Zhe Ming WANG , Chun Hua YAN . X-ray Crystal Structure of a Mononuclear Copper (Ⅱ) Complex withUnusual Monodentate O-coordination of Carboxylate Group ofIsonicotinate. Chinese Chemical Letters, 1998, 9(5): 497-499.
12. [12]
  Cheng He ZHOU , Jun WEI , Zhong Jun LI , Ru Gang XIE , Meng Shen CAI . A New Efficient Synthesis of Bisphenol A Diether Bis-imidazoles and Bis-benzimidazoles. Chinese Chemical Letters, 1998, 9(10): 917-918.
13. [13]
  LI Yan-Hong , LU Li-Ping , ZHU Miao-Li , YUAN Cai-Xia , FENG Si-Si , GAO Zeng-Qiang . A Copper(II) Complex Based on N-(4-hydroxybenzyl)-L-serine: Synthesis, Crystal Structure and Inhibitory Activity on PTP1B and TCPTP. Chinese Journal of Structural Chemistry, 2016, 35(11): 1686-1693. doi: 10.14102/j.cnki.0254-5861.2011-1213
14. [14]
  Qiu Yun CHEN , Qing Shan LIU , Christopher J. SCHOFIELD . Synthesis and Bioassay of 4-Substituted 2-Oxoglutaric Acids. Chinese Chemical Letters, 2006, 17(2): 156-158.
15. [15]
  Bin YAO , You Jun ZHOU , Jü ZHU , Jia Guo Lü , Yao Wu LI , Jun CHENG , Qing Feng JIANG , Can Hui ZHENG . Design, Synthesis and Biological Evaluation of Non-azole Inhibitors of Lanosterol 14α-Demethylase of Fungi. Chinese Chemical Letters, 2006, 17(9): 1189-1192.
16. [16]
  Ai Ping BAI , Zong Ru GUO , Wen Hui HU , Fang SHEN , Gui Fang CHENG . Design, Synthesis and in vitro Evaluation of a New Class of Novel Cyclooxygenase-2 Inhibitors: 3, 4-diaryl-3-pyrrolin-2-ones. Chinese Chemical Letters, 2001, 12(9): 775-778.
17. [17]
  Li Na , Xin Jingchao , Meng Yaqi , Li Erdong , Ma Qisheng , Bao Chongnan , Yang Peng , Song Panpan , Cui Fei , Zhao Peirong , Li Wen , Ke Yu , Zhang Qiurong , Liu Hongmin . Synthesis and Antitumor Evaluation of 2, 4-Substituted Quinazoline Derivatives Containing Benzimidazole. Chinese Journal of Organic Chemistry, 2018, 38(10): 2673-2679. doi: 10.6023/cjoc201804016
18. [18]
  Huo Xinyu , Li Wenbin , Zhang Boya , Chen Xiaofei , Zhou Yueting , Zhang Jie , Han Xiaoqiang , Dai Bin . Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids. Chinese Journal of Organic Chemistry, 2018, 38(12): 3356-3362. doi: 10.6023/cjoc201805053
19. [19]
  CHEN Peng-Yuan , ZHANG Lin , ZHU Shun-Guan , CHENG Guang-Bin . Intermolecular Interactions, Thermodynamic Properties, Detonation Performance, and Sensitivity of TNT/CL-20 Cocrystal Explosive. Chinese Journal of Structural Chemistry, 2016, 35(2): 246-256. doi: 10.14102/j.cnki.0254-5861.2011-0887

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4620)
HTML views(95)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142