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Synthesis of Betti base derivatives catalyzed by nano-CuO-ionic liquid and experimental and quantum chemical studies on corrosion inhibition performance of them

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Abstract

In this research, for the first time, aminonaphthol derivatives were introduced as efficient corrosion inhibitors. A linear polarization method was employed to investigate the corrosion inhibitory effect of the synthesized aminonaphthols at a concentration of 200 ppm for mild steel acid pickling in 1 M HCl and 0.5 M H2SO4 solutions. The results showed that, even in such strongly corrosive media, all of the synthesized aminonaphthol derivatives exhibit good inhibitory effects toward mild steel corrosion with inhibition efficiencies in the range of 84–95%. A facile, efficient and environmentally friendly method has been introduced for the synthesis of aminonaphthol derivatives by nano-CuO in ionic liquid as a novel catalytic system. Mild, one-pot, operational simplicity and reusability of the catalyst make this protocol highly significant. Experiments showed that these compounds can be used as effective corrosion inhibitors for mild steel acid pickling. The semi-emperical B3LYP method was used for the theoretical calculations. The results of quantum chemical studies confirmed the experimental findings.

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References

  1. S. Knapp, Chem. Rev. 95, 1859 (1995)

    Article  CAS  Google Scholar 

  2. Y.F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 104, 4666 (1982)

    Article  Google Scholar 

  3. A.Y. Shen, C.L. Chen, C.I. Lin, Chines. J. Physiol. 35, 45 (1991)

    Google Scholar 

  4. R. Mannhold, H. Kubinyi, Molecular Biology in Medicinal Chemistry, vol. 21, ed. by T. Dingermann, D. Steinhilber, G. Folkers (Wiley, Hoboken, 2006), p. 123

  5. C. Cardellicchio, M.A.M. Capozzi, F. Naso, Tetrahedron Asymmetry 21, 507 (2010)

    Article  CAS  Google Scholar 

  6. Z. Turgut, C. Yolacan, F. Aydogan, E. Bagdatli, N. Ocal, Molecules 12, 2151 (2007)

    Article  CAS  Google Scholar 

  7. I. Szatmári, T.A. Martinek, L. Lázár, A. Koch, E. Kleinpeter, K. Neuvonen, F. Fülöpm, J. Org. Chem. 69, 3645 (2004)

    Article  Google Scholar 

  8. I. Szatmari, A. Hetenyi, L. Lazar, F. Fulop, J. Heterocycl. Chem. 41, 367 (2004)

    Article  CAS  Google Scholar 

  9. Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 382 (1999)

    Article  Google Scholar 

  10. M. Gerlach, C. Maul, US Patent (2007) 7,202,242

  11. M. Heydenreich, A. Koch, S. Klod, I. Szatmári, F. Fülöp, E. Kleinpeter, Tetrahedron 62, 11081 (2006)

    Article  CAS  Google Scholar 

  12. C. Cardellicchio, G. Ciccarella, F. Naso, F. Perna, P. Tortorella, Tetrahedron 55, 14685 (1999)

    Article  CAS  Google Scholar 

  13. D. Tóth, I. Szatmári, M. Heydenreich, A. Koch, E. Kleinpeter, F. Fülöp, J. Mol. Struct. 929, 58 (2009)

    Article  Google Scholar 

  14. J.S. Ghomi, S. Zahedi, M.A. Ghasemzadeh, Mon. Chem. 145, 1191 (2014)

    Article  Google Scholar 

  15. R. Csütörtöki, I. Szatmári, A. Koch, M. Heydenreich, E. Kleinpeter, F. Fülöp, Tetrahedron 67, 8564 (2011)

    Article  Google Scholar 

  16. H.A. Soliman, A.Y. Mubarak, A. El-Mekabaty, H.M. Awad, S.S. Elmorsy, Monatsh. Chem. 147, 809 (2016)

    Article  CAS  Google Scholar 

  17. Z. Cai, C. Shu, Y. Peng, Monatsh. Chem. 145, 1681 (2014)

    Article  CAS  Google Scholar 

  18. S. Rostamizadeh, F. Abdollahi, N. Shadjou, A.M. Amani, Monatsh. Chem. 144, 1191 (2013)

    Article  CAS  Google Scholar 

  19. J.S. Ghomi, S. Zahedi, Monatsh. Chem. 144, 687 (2013)

    Article  CAS  Google Scholar 

  20. A.J. Makawana, B.C. Sangani, Y.F. Yao, Y.T. Duan, P.C. Lv, H.L. Zhu, Mini. Rev. Med. Chem. 16, 1303 (2016)

    Article  CAS  Google Scholar 

  21. K. Kalantar-zadeh, J.Z. Ou, T. Daeneke, A. Mitchell, T. Sasaki, M.S. Fuhrer, Appl. Mater. Today. 5, 73 (2016)

    Article  Google Scholar 

  22. S.G. Babu, R. Karvembu, Catal. Surv. Asia. 17, 156 (2013)

    Article  CAS  Google Scholar 

  23. A.S. Zoolfakar, R.A. Rani, A.J. Morfa, A.P. O’Mullane, K. Kalantar-Zadeh, J. Mater. Chem. C. 2(27), 5247 (2014)

    Article  CAS  Google Scholar 

  24. D. Gangaprasad, J.P. Raj, T. Kiranmye, R. Sasikala, K. Karthikeyan, S.K. Rani, J. Elangovan, Tetrahedron Lett. 57(29), 3105 (2016)

    Article  CAS  Google Scholar 

  25. M.B. Gawande, A. Goswami, F.X. Felpin, T. Asefa, X. Huang, R. Silva, X. Zou, R. Zboril, R.S. Varma, Chem. Rev. 116, 3722 (2016)

    Article  CAS  Google Scholar 

  26. B.C. Ranu, R. Dey, T. Chatterjee, S. Ahammed, Chemsuschem 5, 22 (2012)

    Article  CAS  Google Scholar 

  27. M. Halder, M.M. Islam, Z. Ansari, S. Ahammed, K. Sen, S.M. Islam, A.C.S. Sustain, Chem. Eng. 5, 648 (2016)

    Google Scholar 

  28. K. Kumari, P. Singh, G.K. Mehrotra, Adv. Energy. Mater. 4, 529 (2014)

    Article  Google Scholar 

  29. S.T. Arab, E.A.A. Noor, Corrosion 49, 122 (1993)

    Article  CAS  Google Scholar 

  30. M.A. Arenas, A. Conde, J.J. De Damborenea, Corros. Sci. 44, 511 (2002)

    Article  CAS  Google Scholar 

  31. F. Bentiss, M. Traisnel, M. Lagrenee, Corros. Sci. 42, 127 (2000)

    Article  CAS  Google Scholar 

  32. E. Cano, P. Pinilla, J.L. Polo, J.M. Bastidas, Mater. Corros. 54, 222 (2003)

    Article  CAS  Google Scholar 

  33. A. Chetouani, B. Hammouti, Bull. Electrochem. 19, 23 (2003)

    CAS  Google Scholar 

  34. B. Hammouti, S. Kertit, A. Melhaoui, Bull. Electrochem. 13, 97 (1997)

    CAS  Google Scholar 

  35. B. Hammouti, S. Kertit, A. Melhaoui, Bull. Electrochem. 11, 553 (1995). (India)

    CAS  Google Scholar 

  36. M.G. Hosseini, M. Ehteshamzadeh, T. Shahrabi, Electrochim. Acta 52, 3680 (2007)

    Article  CAS  Google Scholar 

  37. Y.W. Kim, J.G. Kim, D.J. Choi, Mater. Corros. 52, 697 (2001)

    Article  Google Scholar 

  38. M. Lagrenee, B. Mernari, N. Chaibi, M. Traisnel, H. Vezin, F. Bentiss, Corros. Sci. 43, 951 (2001)

    Article  CAS  Google Scholar 

  39. H. Luo, Y.C. Guan, K.N. Han, Corrosion 54, 619 (1998)

    Article  CAS  Google Scholar 

  40. S. Martinez, Mater. Chem. Phys. 77, 97 (2003)

    Article  CAS  Google Scholar 

  41. G. Moretti, F. Guidi, G. Grion, Corros. Sci. 46, 387 (2004)

    Article  CAS  Google Scholar 

  42. R.M. Saleh, AAEl Ismall, A.A. Hosary, Br. Corros. J. 17, 131 (1982)

    Article  CAS  Google Scholar 

  43. B. Sanyal, Prog. Org. Coat. 9, 165 (1981)

    Article  CAS  Google Scholar 

  44. T. Shahrabi, H. Tavakholi, M.G. Hosseini, Anti-Corros. Method Mater. 54, 308 (2007)

    Article  CAS  Google Scholar 

  45. K. Srivastava, P. Srivastava, Br. Corros. J. 16, 221 (1981)

    Article  CAS  Google Scholar 

  46. H.H. Uhlig, Corrosion and Corrosion Control (Wiley, New York, 1963)

    Google Scholar 

  47. R. Teimuri-Mofrad, A. Shahrisa, M. Gholamhosseini-Nazari, N. Arsalani, Res. Chem. Intermed. 42, 3425 (2016)

    Article  CAS  Google Scholar 

  48. A. Shahrisa, R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, Mol. Divers 19, 87 (2015)

    Article  CAS  Google Scholar 

  49. A. Shahrisa, R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, Synlett 26, 1031 (2015)

    Article  CAS  Google Scholar 

  50. R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, S. Esmati, A. Shahrisa, Res. Chem. Intermed. 43, 6845 (2017)

    Article  CAS  Google Scholar 

  51. R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, E. Payami, S. Esmati, Appl. Organomet. Chem. 32, 1 (2018)

    Article  Google Scholar 

  52. R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, S. Esmati, A. Shahrisa, J. Chem. Sci. 129, 1449 (2017)

    Article  CAS  Google Scholar 

  53. S. Xia, M. Qiu, L. Yu, F. Liu, H. Zhao, Corros. Sci. 50, 2021 (2008)

    Article  CAS  Google Scholar 

  54. E.E. Ebenso, T. Arslan, F. Kandemirli, N. Caner, I. Love, Int. J. Quantum Chem. 110, 1003 (2010)

    Article  CAS  Google Scholar 

  55. Y.M. Tang, W.Z. Yang, X.S. Yin, Y. Liu, R. Wan, J.T. Wang, Mater. Chem. Phys. 116, 479 (2009)

    Article  CAS  Google Scholar 

  56. V.S. Sastri, J.R. Perumareddi, Corrosion 53, 617 (1997)

    Article  CAS  Google Scholar 

  57. I. Lukovits, E. Kalman, F. Zucchi, Corrosion 57, 3 (2001)

    Article  CAS  Google Scholar 

  58. R.G. Pearson, J. Org. Chem. 54, 1423 (1989)

    Article  CAS  Google Scholar 

  59. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. Petersson, H. Nakatsuji, Gaussian 09, revision a. 02, gaussian. Inc., Wallingford, CT. 2009 11:200

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Acknowledgements

The authors would like to acknowledge the financial support from the Iran National Science Foundation (INSF) and the University of Tabriz.

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Correspondence to Reza Teimuri-Mofrad.

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11164_2018_3287_MOESM1_ESM.docx

Detailed procedure for preparation and characterization of catalyst with spectral data and scan spectra of all compounds are available. Also, the optimized structure, HOMO and LUMO distribution for compound 4aq are presented. Supplementary data associated with this article can be found via the ‘‘Supplementary Content’’ section of this article’s webpage. (DOCX 15265 kb)

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Teimuri-Mofrad, R., Ahadzadeh, I., Gholamhosseini-Nazari, M. et al. Synthesis of Betti base derivatives catalyzed by nano-CuO-ionic liquid and experimental and quantum chemical studies on corrosion inhibition performance of them. Res Chem Intermed 44, 2913–2927 (2018). https://doi.org/10.1007/s11164-018-3287-2

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