Citation: 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[J]. Acta Physico-Chimica Sinica, ;2013, 29(06): 1192-1200. doi: 10.3866/PKU.WHXB201303154 shu

HQSAR Study and Molecular Design of Benzimidazole Derivatives as Corrosion Inhibitors

1.
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

Received Date: 15 January 2013
Available Online: 15 March 2013
Fund Project: 山东省自然科学基金(ZR2012BM010) (ZR2012BM010)中国石油科技创新基金项目(2011D-5006-0202)资助 (2011D-5006-0202)

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 (SE_cv) value of 3.709, which indicates od 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.
- Benzimidazole,
- Corrosion inhibitor,
- Hologram quantitative structure-activity relationship,
- Molecular design
1. [1]
  
  (1) Migahed, M. A. Mater. Chem. Phys. 2005, 93 (1), 48. doi: 10.1016/j.matchemphys.2005.02.003
2. [2]
  (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. [3]
  (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. [4]
  (4) Khaled, K. F. Electrochim. Acta 2003, 48 (17), 2493. doi: 10.1016/S0013-4686(03)00291-3
5. [5]
  (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. [6]
  (6) Trabanelli, G. Corrosion 1991, 47 (6), 410. doi: 10.5006/1.3585271
7. [7]
  (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. [8]
  (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. [9]
  (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. [10]
  (10) Hansch, C.; Fujita, T. J. Am. Chem. Soc. 1964, 86 (8), 1616. doi: 10.1021/ja01062a035
11. [11]
  (11) Bentiss, F.; Traisnel, M.; Vezin, H.; Lagrenée, M. Corrosion Sci.2003, 45 (2), 371. doi: 10.1016/S0010-938X(02)00102-6
12. [12]
  (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. [13]
  (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. [14]
  (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. [15]
  (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. [16]
  (16) Ashry, E. S. H. E.; Senior, S. A. Corrosion Sci. 2011, 53 (3),1025. doi: 10.1016/j.corsci.2010.11.037
17. [17]
  (17) Marshall, G. R.; Cramer, R. D. Trends. Pharmacol. Sci. 1988, 9 (8), 285. doi: 10.1016/0165-6147(88)90012-0
18. [18]
  (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. [19]
  (19) Winkler, D. A.; Burden, F. R. Quant. Struct. -Act. Relat. 1998, 17 (3), 224.
20. [20]
  (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. [21]
  (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. [22]
  (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. [23]
  (23) Ye, M.; Dawson, M. I. Bioorg. Med. Chem. Lett. 2009, 19 (12),3310. doi: 10.1016/j.bmcl.2009.04.072
24. [24]
  (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. [25]
  (25) Popova, A.; Sokolova, E.; Raicheva, S.; Christov, M. CorrosionSci. 2003, 45 (1), 33. doi: 10.1016/S0010-938X(02)00072-0
26. [26]
  (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. [27]
  (27) Aljourani, J.; Raeissi, K.; lozar, M. A. Corrosion Sci. 2009, 51 (8), 1836. doi: 10.1016/j.corsci.2009.05.011
28. [28]
  (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. [29]
  (29) Sybyl Software, Version 8.1; Tripos Associates Inc.: St. Louis,MO, USA, 2008.
30. [30]
  (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. [31]
  (31) Flower, R. D. J. Chem. Inf. Comput. Sci. 1998, 38 (3), 379. doi: 10.1021/ci970437z
32. [32]
  (32) Bush, B. L.; Nachbar, R. B. J. Comput. -Aided. Mol. Des. 1993,7(5), 587. doi: 10.1007/BF00124364
33. [33]
  (33) Wold, S.; Sjöström, M.; Eriksson, L. Chemom. Intell. Lab. Syst.2001, 58 (2), 109. doi: 10.1016/S0169-7439(01)00155-1
34. [34]
  (34) Cawley, G. C.; Talbot, N. L. C. Neural Netw. 2004, 17 (10),1467. doi: 10.1016/j.neunet.2004.07.002
35. [35]
  (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. [1]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
2. [2]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
3. [3]
  Kai Yang , Gehua Bi , Yong Zhang , Delin Jin , Ziwei Xu , Qian Wang , Lingbao Xing . Comprehensive Polymer Chemistry Experiment Design: Preparation and Characterization of Rigid Polyurethane Foam Materials. University Chemistry, 2024, 39(4): 206-212. doi: 10.3866/PKU.DXHX202308045
4. [4]
  Hongyun Liu , Jiarun Li , Xinyi Li , Zhe Liu , Jiaxuan Li , Cong Xiao . Course Ideological and Political Design of a Comprehensive Chemistry Experiment: Constructing a Visual Molecular Logic System Based on Intelligent Hydrogel Film Electrodes. University Chemistry, 2024, 39(2): 227-233. doi: 10.3866/PKU.DXHX202309070
5. [5]
  Shuang Meng , Haixin Long , Zhou Zhou , Meizhu Rong . Inorganic Chemistry Curriculum Design and Implementation of Based on “Stepped-Task Driven + Multi-Dimensional Output” Model: A Case Study on Intermolecular Forces. University Chemistry, 2024, 39(3): 122-131. doi: 10.3866/PKU.DXHX202309008
6. [6]
  Feng Zheng , Ruxun Yuan , Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027
7. [7]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
8. [8]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
9. [9]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
10. [10]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
11. [11]
  Yong Shu , Xing Chen , Sai Duan , Rongzhen Liao . How to Determine the Equilibrium Bond Distance of Homonuclear Diatomic Molecules: A Case Study of H₂. University Chemistry, 2024, 39(7): 386-393. doi: 10.3866/PKU.DXHX202310102
12. [12]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
13. [13]
  Laiying Zhang , Yinghuan Wu , Yazi Yu , Yecheng Xu , Haojie Zhang , Weitai Wu . Innovation and Practice of Polymer Chemistry Experiment Teaching for Non-Polymer Major Students of Chemistry: Taking the Synthesis, Solution Property, Optical Performance and Application of Thermo-Sensitive Polymers as an Example. University Chemistry, 2024, 39(4): 213-220. doi: 10.3866/PKU.DXHX202310126
14. [14]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
15. [15]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
16. [16]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
17. [17]
  Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029
18. [18]
  Wenbing Hu , Jin Zhu . Flipped Classroom Approach in Teaching Professional English Reading and Writing to Polymer Graduates. University Chemistry, 2024, 39(6): 128-131. doi: 10.3866/PKU.DXHX202310015
19. [19]
  Zongpei Zhang , Yanyang Li , Yanan Si , Kai Li , Shuangquan Zang . Developing a Chemistry Experiment Center Employing a Multifaceted Approach to Serve High-Quality Laboratory Education. University Chemistry, 2024, 39(7): 13-19. doi: 10.12461/PKU.DXHX202404041
20. [20]
  Pingping Zhu , Yongjun Xie , Yuanping Yi , Yu Huang , Qiang Zhou , Shiyan Xiao , Haiyang Yang , Pingsheng He . Excavation and Extraction of Ideological and Political Elements for the Virtual Simulation Experiments at Molecular Level: Taking the Project “the Simulation and Computation of Conformation, Morphology and Dimensions of Polymer Chains” as an Example. University Chemistry, 2024, 39(2): 83-88. doi: 10.3866/PKU.DXHX202309063

Get Citation

PDF

XML

Metrics

PDF Downloads(830)
Abstract views(779)
HTML views(21)

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