Electrochemical oxidation of 4-amino phenol in the presence of 2-mercaptobenzimidazoles and synthesis of new organosulfur compounds

Document Type : Original Article

Authors

1 Nahavand Higher Education Complex, Bu-Ali Sina University, Hamedan, Iran

2 Faculty of Chemistry, Bu-Ali-Sina University, Hamedan, Iran.

Abstract

In this research, the electrochemical oxidation of 4-amino phenol (1) was studied by cyclic voltammetry and controlled potential coulometryin in the absence and presence of 2-mercaptobenzimidazole (3a), 2-mercapto-5-methyl benzimidazole (3b) and 2-mercapto-5-metoxy benzimidazole (3c) in aqueous/ethanol (70/30 v/v) mixture.The results revealed that p-quinone(2) derived from oxidation of 4-amino phenol (1) participate in Michaeladdition reactions with 3a-c via EC mechanism. To confirm the proposed mechanism, the electrochemical synthesis of 4-amino phenol (1) was performed in the presence of 2-mercapto benzimidazoles (3a-c), and the obtained products were identified by 1HNMR, FTIR and Mass spectroscopy. In this study, we synthesized a variety of products with good efficiency using controlled potential electrochemical oxidation at a surface of graphite electrode.

Keywords

References

[1] D. Nematollahi and A. Maleki. Electrochem. Commun. 11 (2009) 488.
[2] A. J. Bard and L. R. Faulkner. Electrochemical Methods. 2nd ed. New York, Wiley (2001).
[3] E. Tammari. A. Amani. D. Nematollahi. R. Jalili and M. Kazemi. Res. J. Chem. Environ. 17 (2013) 41.
[4] E. Tammari. M. Kazemi and A. Amani. J. Electrochem. Soc. 161 (2014) G69.
[5] S. A. Nevade. S. G. Lokapure. and N. V. Kalyane. J. Korean. Chem Soc. 57(2013) 755.
[6] M. V. Dealmeida. S. H. Cardoso. J. V. Deassis. M. V. N. Desouza. J. Sulfur Chem. 28 (2007) 17.
[7] M. Joudaki. D. Nematollahi. J. Electrochem. Soc. 165 (2018) G133.
[8] H. Beiginejad. D. Nematollahi. S. Khazalpour. J. Of Applied Chemistry 13 (2018) 75. in Persian.
[9] A. Asghari. M. Ameri. S. Radmannia. M.Rajabi. M. Bakherad and D.Nematollahi J. Electroanal. Chem. 733 (2014) 47.
[10] M. Bashiri. E. Tammari. F. Ganjeizadeh Rohani. J. Of Applied Chemistry 14 (2019) 177. in Persian.
[11] A. Amani. D. Nematollahi, J. Org. Chem. 77 (2012) 11302.
[12] E. Salahifar, D. Nematollahi, M. Bayat, A. Mahyari, and H. Amiri Rudbari, Org. Lett. (2015) DOI: 10.1021/acs.orglett.5b01837.
[13] M. R. Vinutha. T. V. Venkatesha. C. Nagaraja. Int. J. Ind. Chem. 9 (2018)185.
Applied Chemistry Today
Volume 16, Issue 60
September 2021
Pages 79-94

Files

Share

How to cite

Statistics