Vol.5 , No. 1, Publication Date: Feb. 1, 2018, Page: 8-16
[1] | Firoz Ahmed, Department of Chemistry, Khulna University of Engineering and Technology, Khulna, Bangladesh. |
[2] | Nazim Uddin, Department of Chemistry, Khulna University of Engineering and Technology, Khulna, Bangladesh. |
[3] | Abdul Aziz, Department of Chemistry, Khulna University of Engineering and Technology, Khulna, Bangladesh. |
[4] | Abdul Motin, Department of Chemistry, Khulna University of Engineering and Technology, Khulna, Bangladesh. |
[5] | Abdul Hafiz Mia, Department of Chemistry, Khulna University of Engineering and Technology, Khulna, Bangladesh. |
The electrochemical behavior of 1,2-dihydroxy benzene in presence of different concentration of L-Valine in aqueous solution with various pH values (5-11), different electrodes (Pt, Au, GC) were studied by using cyclic voltammetry, controlled potential Coulometry and differential pulse voltammetry. Electro-oxidation of 1,2-dihydroxy benzene generates o-benzoquinone which acts as Michael acceptor. L-Valine acts as a nucleophile and undergoes 1,4-Michael addition reaction with 1,2-dihydroxy benzene. The reaction of o-benzoquinone with L-Valine at moderately high concentration of nucleophiles was observed in second scan of potential. After occurring electro-oxidation the product is assumed to be 2-((3,4-dioxocyclohexa-1,5-dien-1-yl)amino)-3-methylbutanoic acid that undergoes electron transfer at more negative potentials than the 1,2-dihydroxy benzene. The reaction was strongly influenced by pH as well as concentration of L-Valine. The concentration effect of nucleophile with fixed concentration of 1,2-dihydroxy benzene (2 mM) was measured from 30 mM to 200 mM. This nucleophilic addition reaction was most suitable in 100 mM of L-Valine and 2 mM of 1,2-dihydroxy benzene at pH 7. The behavior of the reaction was of ECE type followed by diffusion mechanism.
Keywords
Cyclic Voltammetry, Differential Pulse Voltammetry, 1,2-Dihydroxy Benzene, L-Valine, ECE Mechanism
Reference
[01] | Fiegel, Helmut et al. (2002) "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim. doi: 10.1002/14356007.a19_313. |
[02] | Barner, B. A. (2004) "1,2-dihydroxy benzene" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette), J. Wiley & Sons, New York. |
[03] | R. H. Bisby, R. Brooke, S. Navaratnam, Food Chem. 108 (2008) 1002. |
[04] | M. Rafiee, Synlett 3 (2007) 503. |
[05] | D. Nematollahi, M. Rafiee, L. Fotouhi, J. Iranian Chemical Society 6 (2009) 448. |
[06] | Encyclopaedia Britannica Online. Retrieved 2015-12-06. |
[07] | Merriam-Webster Online Dictionary. Retrieved 2015-12-06. |
[08] | https://en.wikipedia.org/wiki/L-Valine. |
[09] | A. Kiani, J. B. Raoof, D. Nematollahi, R. Ojania, Electroanalysis 17 (2005) 1755. |
[10] | D. Nematollahi, S. M. Golabi, J. Electroanal. Chem. 481 (2000) 208. |
[11] | S. Shahrokhian, A. Hamzehloei, Electrochem. Commun. 5 (2003) 1006. |
[12] | D. Nematollahi, S. M. Golabi, Electroanalysis 13 (2001) 1008. |
[13] | Z. Grujic, I. Tabakovic, M. Trkovnic, Tetrahedron Lett. 52 (1976) 4823. |
[14] | D. Nematollahi, H. Goodarzi, J. Electroanal. Chem. 510 (2001) 108. |
[15] | I. Tabakovic, Z. Grujic, Z. Bejtovic, J. Heterocyclic Chem. 20 (1983) 635. |
[16] | D. Nematollahi, Z. Forooghi, Tetrahedron 58 (2002) 4949. |
[17] | S. M. Golabi, F. Nourmohammadi, A. Saadnia, J. Electroanal. Chem. 529 (2002) 12. |
[18] | L. Papouchado, R. W. Sandford, G. Petrie, R. N. Adams, J. Electroanal. Chem. 65 (1975) 275. |
[19] | P. A. Thibodeau, B. Paquette, Free Radic. Biol. Med. 27 (1999) 1367 |
[20] | P. Belenky, K. L. Bogan, C. Brenner, Trends Biochem. Sci. 32 (2007) 9. |
[21] | S. Mazzini, R. Monderelli, E. Ragg, L. Scaglioni, J. Chem. Soc. Perkin Trans. 2 (1995) 285. |
[22] | D. Nematollahi, A. Afkhami, F. Mosaed, M. Rafiee, Research on Chemical Intermediates 30 (2004) 299. |
[23] | L. Papouchado, G. Petrie, R. N. Adams, J. Electroanal. Chem. 38 (1972) 389. |
[24] | L. Papouchado, G. Petrie, J. H. Sharp, R. N. Adams, J. Am. Chem. Soc. 90 (1968) 5620. |
[25] | T. E. Young, J. R. Griswold, M. H. Hulbert, J. Org. Chem. 39 (1974) 1980. |
[26] | A. Brun, R. Rosset, J. Electroanal. Chem. 49 (1974) 287. |
[27] | D. I. Stum, S. N. Suslov, Bio. Zika 21 (1979) 40. |
[28] | M. D. Rayn, A. Yueh, C. W. Yu, J. Electrochem. Soc. 127 (1980) 1489. |