Please wait a minute...
Acta Phys. Chim. Sin.  2013, Vol. 29 Issue (06): 1192-1200    DOI: 10.3866/PKU.WHXB201303154
THEORETICAL AND COMPUTATIONAL CHEMISTRY     
HQSAR Study and Molecular Design of Benzimidazole Derivatives as Corrosion Inhibitors
SUN Sang-Dun1, MI Si-Qi2, YOU Jing3, YU Ji-Liang3, HU Song-Qing2, LIU Xin-Yong4
1 Oil Production Technology Research Institute of Shengli Oilfield, Dongying 257061, Shandong Province, P. R. China;
2 College of Science, China University of Petroleum (East China), Qingdao 266580, Shandong Province, P. R. China;
3 Oil Production Engineering Research Institute of Huabei Oilfield, Renqiu 062500, Hebei Province, P. R. China;
4 College of Pharmacy, Shandong University, Jinan 250012, P. R. China
Download:   PDF(808KB) Export: BibTeX | EndNote (RIS)      

Abstract  

Hologram quantitative structure-activity relationship (HQSAR) analysis was conducted on a series of benzimidazole compounds to build the HQSAR model between corrosion inhibition properties and molecular structures in acid environment. The optimal HQSAR model was determined by investigating the influence of different fragment distinction and fragment size on the models, and the models’ stability and predictive ability were evaluated. The results show that the optimal HQSAR model was generated using atoms(A), bonds(B), connectivity(C), hydrogen(H), chirality(Ch), donor and acceptor(D&A) as fragment distinction and fragment size of 1-3. The model had a non-cross validated coefficient (r2) value of 0.996, a cross-validated (q2) value of 0.960, and a cross-validated standard error (SEcv) value of 3.709, which indicates good statistics stability and predictive power. On the basis of the maps derived from the optimal HQSAR model, 38 new benzimidazole derivatives were designed and screened using the optimal HQSAR model, giving potential candidates with high predictive inhibition efficiency. This work provides valuable information for further research and design of more promising corrosion inhibitors in the oil and gas field.



Key wordsBenzimidazole      Corrosion inhibitor      Hologram quantitative structure-activity relationship      Molecular design     
Received: 15 January 2013      Published: 15 March 2013
MSC2000:  O641  
Fund:  

The project was supported by the Natural Science Foundation of Shandong Provice, China (ZR2012BM010) and CNPC Innovation Foundation, China (2011D-5006-0202).

Cite this article:

SUN Sang-Dun, MI Si-Qi, YOU Jing, YU Ji-Liang, HU Song-Qing, LIU Xin-Yong. HQSAR Study and Molecular Design of Benzimidazole Derivatives as Corrosion Inhibitors. Acta Phys. Chim. Sin., 2013, 29(06): 1192-1200.

URL:

http://www.whxb.pku.edu.cn/Jwk_wk/wlhx/10.3866/PKU.WHXB201303154     OR     http://www.whxb.pku.edu.cn/Jwk_wk/wlhx/Y2013/V29/I06/1192

(1) Migahed, M. A. Mater. Chem. Phys. 2005, 93 (1), 48. doi: 10.1016/j.matchemphys.2005.02.003
(2) Abd El-Maksoud, S. A.; Fouda, A. S. Mater. Chem. Phys. 2005,93 (1), 84. doi: 10.1016/j.matchemphys.2005.02.020
(3) Mernari, B.; Elattari, H.; Traisnel, M.; Bentiss, F.; Lagrenee, M.Corrosion Sci. 1998, 40 (2-3), 391. doi: 10.1016/S0010-938X(97)00142-X
(4) Khaled, K. F. Electrochim. Acta 2003, 48 (17), 2493. doi: 10.1016/S0013-4686(03)00291-3
(5) Mu, G. N.; Li, X. H.; Qu, Q.; Zhou, J. Corrosion Sci. 2006, 48 (2), 445. doi: 10.1016/j.corsci.2005.01.013
(6) Trabanelli, G. Corrosion 1991, 47 (6), 410. doi: 10.5006/1.3585271
(7) Gómez, B.; Likhanova, N. V.; Domínguez Aguilar, M. N.;Olivares, O.; Hallen, J. M.; Martínez-Magadán, J. M. J. Phys.Chem. A 2005, 109 (39), 8950. doi: 10.1021/jp052188k
(8) Wang, X. M.; Yang, H. Y.; Wang, F. H. Corrosion Sci. 2011, 53 (1), 113. doi: 10.1016/j.corsci.2010.09.029
(9) Wang, P. Quantitative Structure-Activity Relationship andResearch Methods; Harbin Institute of Technology Press:Harbin, 2004; pp 1-3. [王鹏.定量构效关系及研究方法.哈尔滨: 哈尔滨工业大学出版社, 2004: 1-3.]
(10) Hansch, C.; Fujita, T. J. Am. Chem. Soc. 1964, 86 (8), 1616. doi: 10.1021/ja01062a035
(11) Bentiss, F.; Traisnel, M.; Vezin, H.; Lagrenée, M. Corrosion Sci.2003, 45 (2), 371. doi: 10.1016/S0010-938X(02)00102-6
(12) Khaled, K. F.; Babi?-Samard?ija, K.; Hackerman, N.Electrochim. Acta 2005, 50 (12), 2515. doi: 10.1016/j.electacta.2004.10.079
(13) Zhang, S. G.; Lei, W.; Xia, M. Z.; Wang, F. Y. J. Mol.Struct.-Theochem 2005, 732 (1-3), 173. doi: 10.1016/j.theochem.2005.02.091
(14) Lebrini, M.; Traisnel, M.; Lagrenée, M.; Mernari, B.; Bentiss, F.Corrosion. Sci. 2008, 50 (2), 473. doi: 10.1016/j.corsci.2007.05.031
(15) Hu, S. Q.; Hu, J. C.; Shi, X.; Zhang, J.; Guo, W. Y. ActaPhys. -Chim. Sin. 2009, 25 (12), 2524. [胡松青, 胡建春, 石鑫,张军,郭文跃.物理化学学报, 2009, 25 (12), 2524.]doi: 10.3866/PKU.WHXB20091126
(16) Ashry, E. S. H. E.; Senior, S. A. Corrosion Sci. 2011, 53 (3),1025. doi: 10.1016/j.corsci.2010.11.037
(17) Marshall, G. R.; Cramer, R. D. Trends. Pharmacol. Sci. 1988, 9 (8), 285. doi: 10.1016/0165-6147(88)90012-0
(18) Hu, S. Q.; Mi, S. Q.; Jia, X. L.; Guo, A. L.; Chen, S. H.; Zhang,J.; Liu, X. Y. Chem. J. Chin. Univ. 2011, 32 (10), 2402. [胡松青,米思奇, 贾晓林,郭爱玲, 陈生辉,张军,刘新泳.高等学校化学学报, 2011, 32 (10), 2402.]
(19) Winkler, D. A.; Burden, F. R. Quant. Struct. -Act. Relat. 1998, 17 (3), 224.
(20) Chen, D.; Yin, C. S.; Wang, X. D.; Wang, L. S. Chemosphere2004, 57 (11), 1739. doi: 10.1016/j.chemosphere.2004.08.075
(21) Honorio, K. M.; Garratt, R. C.; Andricopulo, A. D. Bioorg. Med.Chem. Lett. 2005, 15 (12), 3119. doi: 10.1016/j.bmcl.2005.04.017
(22) Nair, P. C.; Srikanth, K.; Sobhia, M. E. Bioorg. Med. Chem.Lett. 2008, 18 (4), 1323. doi: 10.1016/j.bmcl.2008.01.023
(23) Ye, M.; Dawson, M. I. Bioorg. Med. Chem. Lett. 2009, 19 (12),3310. doi: 10.1016/j.bmcl.2009.04.072
(24) Cheng, Y. H.; Zhou, M.; Tung, C. H.; Ji, M. J.; Zhang, F. S.Med. Chem. Lett. 2010, 20 (11), 3329. doi: 10.1016/j.bmcl.2010.04.033
(25) Popova, A.; Sokolova, E.; Raicheva, S.; Christov, M. CorrosionSci. 2003, 45 (1), 33. doi: 10.1016/S0010-938X(02)00072-0
(26) Abboud, Y.; Abourriche, A.; Saffaj, T.; Berrada, M.; Charrouf,M.; Bennamara, A.; Cherqaoui, A.; Takky, D. Appl. Surf. Sci.2006, 252 (23), 8178. doi: 10.1016/j.apsusc.2005.10.060
(27) Aljourani, J.; Raeissi, K.; Golozar, M. A. Corrosion Sci. 2009, 51 (8), 1836. doi: 10.1016/j.corsci.2009.05.011
(28) Benabdellah, M.; Tounsi, A.; Khaled, K. F.; Hammouti, B. Arab.J. Chem. 2011, 4 (1), 17. doi: 10.1016/j.arabjc.2010.06.010
(29) Sybyl Software, Version 8.1; Tripos Associates Inc.: St. Louis,MO, USA, 2008.
(30) Doddareddy, M. R.; Lee, Y. J.; Cho, Y. S.; Choi, K.; Koh, H. Y.;Pae, A. N. Bioorg. Med. Chem. Lett. 2004, 12 (14), 3815. doi: 10.1016/j.bmc.2004.05.005
(31) Flower, R. D. J. Chem. Inf. Comput. Sci. 1998, 38 (3), 379. doi: 10.1021/ci970437z
(32) Bush, B. L.; Nachbar, R. B. J. Comput. -Aided. Mol. Des. 1993,7(5), 587. doi: 10.1007/BF00124364
(33) Wold, S.; Sjöström, M.; Eriksson, L. Chemom. Intell. Lab. Syst.2001, 58 (2), 109. doi: 10.1016/S0169-7439(01)00155-1
(34) Cawley, G. C.; Talbot, N. L. C. Neural Netw. 2004, 17 (10),1467. doi: 10.1016/j.neunet.2004.07.002
(35) Clark, M.; Cramer, R. D.; Jones, D. M.; Patterson, D. E.;Simeroth, P. E. Tetrahedron Comput. Method 1990, 3 (1), 47.doi: 10.1016/0898-5529(90)90120-W

[1] ZHANG Shao-Qing, HOU Jian-Hui. Rational Design Strategies for Polymer Donors for Applications in Non-Fullerene Organic Photovoltaic Cells[J]. Acta Phys. Chim. Sin., 2017, 33(12): 2327-2338.
[2] WANG Tai-Yang, ZOU Chang-Jun, LI Dai-Xi, CHEN Zheng-Long, LIU Yuan, LI Xiao-Ke, LI Ming. Theoretical Investigation on Cyclodextrin Inclusion Complexes with Organic Phosphoric Acid as Corrosion Inhibitor[J]. Acta Phys. Chim. Sin., 2015, 31(12): 2294-2302.
[3] LI Xiang-Hong, XIE Xiao-Guang. Inhibition Effect of Pyrimidine Derivatives on the Corrosion of Steel in Hydrochloric Acid Solution[J]. Acta Phys. Chim. Sin., 2013, 29(10): 2221-2231.
[4] ZHAO Shun-Sheng, ZHANG Zhao, SHI Guo-Xiang, FENG Wei-Xu, LÜ Xing-Qiang, LIU Xiang-Rong. Heterobinuclear Zn-Eu or Zn-Tb Complexes Formed from Benzimidazole Derivatives and Metal Salts: Synthesis, Structures and Photophysical Properties[J]. Acta Phys. Chim. Sin., 2013, 29(07): 1408-1414.
[5] DUAN Lin-Qiang, QIAO Cheng-Fang, WEI Qing, XIA Zheng-Qiang, CHEN San-Ping, ZHANG Guo-Chun, ZHOU Chun-Sheng, GAO Sheng-Li. Structures, Thermodecomposition Kinetics and Luminescence Properties of Three Lanthanide-Based Supramolecular Compounds with 1H-Benzimidazole-2-carboxylic Acid[J]. Acta Phys. Chim. Sin., 2012, 28(12): 2783-2789.
[6] YANG Rong-Jie, GUO Ya, TANG Fang-Miao, WANG Xiao-Ping, DU Rong-Gui, LIN Chang-Jian. Effect of Sodium D-Gluconate-Based Inhibitor in Preventing Corrosion of Reinforcing Steel in Simulated Concrete Pore Solutions[J]. Acta Phys. Chim. Sin., 2012, 28(08): 1923-1928.
[7] LIU Xiao-Jun, LIN Tao, GAO Shao-Wei, MA Rui, ZHANG Jin-Yue, CAI Xin-Chen, YANG Lei, TENG Feng. TDDFT Investigation and Design for Fluorescent Molecules with Push-Pull Structures[J]. Acta Phys. Chim. Sin., 2012, 28(06): 1337-1346.
[8] ZHAO Jing-Mao, LI Jun. Corrosion Inhibition Performance of Carbon Steel in Brine Solution Containing H2S and CO2by Novel Gemini Surfactants[J]. Acta Phys. Chim. Sin., 2012, 28(03): 623-629.
[9] LI Xiang-Hong, DENG Shu-Duan, FU Hui. Inhibition Effect of Nitrotetrazolium Blue Chloride on the Corrosion of Steel in Hydrochloric Acid Solution[J]. Acta Phys. Chim. Sin., 2011, 27(12): 2841-2848.
[10] ZHOU Xin, YANG Huai-Yu, WANG Fu-Hui. Corrosion Inhibition by Sorbitol/Diethylenetriamine Condensation Product for Carbon Steel in 3.5% NaCl Saturated Ca(OH)2 Solution[J]. Acta Phys. Chim. Sin., 2011, 27(03): 647-654.
[11] ZHANG Qi-Bo, HUA Yi-Xin. Effect of Alkylimidazolium Ionic Liquids on the Corrosion Inhibition of Copper in Sulfuric Acid Solution[J]. Acta Phys. Chim. Sin., 2011, 27(03): 655-663.
[12] DONG Ze-Hua, SHI Wei, GUO Xing-Peng. Localized Corrosion Inhibition of Carbon Steel in Carbonated Concrete Pore Solutions Using Wire Beam Electrodes[J]. Acta Phys. Chim. Sin., 2011, 27(01): 127-134.
[13] QIAO Gui-Min, REN Zhen-Jia, ZHANG Jun, HU Song-Qing, YAN You-Guo, TI Yang. Molecular Dynamics Simulation of Corrosive Medium Diffusion in Corrosion Inhibitor Membrane[J]. Acta Phys. Chim. Sin., 2010, 26(11): 3041-3046.
[14] ZHENG Lei-Gang, YANG Huai-Yu. Influence of Organic Inhibitors on the Corrosion Behavior of Steel Rebar insideMortar Specimens Immersed in Saturated NaCl Solution[J]. Acta Phys. Chim. Sin., 2010, 26(09): 2354-2360.
[15] HU Song-Qing, HU Jian-Chun, FAN Cheng-Cheng, MI Si-Qi, ZHANG Jun, GUO Wen-Yue. Corrosion Inhibition of Q235 Steel by a Novel Imidazoline Compound under H2S and CO2 Coexistence[J]. Acta Phys. Chim. Sin., 2010, 26(08): 2163-2170.