Kinetics and Mechanism of 2-Phenyl-1H-Benzo[d]Imidazole Derivatives Formation: Catalyzed by Glucose
[1]
Mehdi Shahraki, Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran.
[2]
Sayyed Mostafa Habibi-Khorassani, Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran.
[3]
Malek Taher Maghsoodlou, Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran.
[4]
Tahere Zarei, Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran.
[5]
Mohammad Saeed Kazemidoost, Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran.
Sucrose as a green and biodegradable catalyst has been used for the synthesis of 2-phenyl-1H-benzo[d]imidazole derivatives from the reaction of o-phenylenediamine and arylaldehydes under optimal experimental conditions. Kinetics of the two-component reaction of o-phenylenediamine and benzaldehyde has been spectrally studied and the kinetic data along with relevant activation parameters (Ea, ∆H‡, ∆S‡ and ∆G‡) have been determined. The reaction followed second-order kinetics overall and partial-orders respect to the both reactants were one. The effects of solvent, temperature and concentration of the catalyst on the reaction rate were also investigated. Furthermore, the kinetic results confirmed the proposed mechanism and showed the first and second steps could be a rate-determining step (RDS).
Catalyst, Sucrose, Kinetics, Mechanism, Imidazole Derivative
[1]
Alan R. Katritzky; Rees. Comprehensive Heterocyclic Chemistry. Vol. 5, p.469-498, (1984)
[2]
Pozharskii, A.F, et al. Heterocycles in Life and Society. John Wiley & Sons, (1997).
[3]
Castaño T, Encinas A, Pérez C, Castro A, Campillo NE, Gil C. Bioorg Med Chem. 16 (11) : 6193-206 (2008).
[4]
R.G. Ingle. And D.D. Magar Int. J. Drug Res. Tech. 2011, 1 (1), 26-32
[5]
S.L. Khokra, D. Choudhary, Asian Journal of Biochemical and Pharmaceutical Research, 2011, 1(3), 476-486.
[6]
HA. Barker, RD. Smyth, H. Weissbach, J.I. Toohey, JN. Ladd and BE. Volcani, Journal of Biological Chemistry. 1960, 235(2), 480-488.
[7]
Grimmett, M. Ross. Imidazole and Benzimidazole Synthesis. Academic Press, (1997).
[8]
US patent 6,177,575, A. J. Arduengo, "Process for Manufacture of Imidazoles", issued 2001-01-23
[9]
H. Sharghi, M. H. Beyzavi, and M. M. Doroodmand, Eur. J. Org. Chem., 2008, 4126.
[10]
M.Amiri Z.Karimi-Jaberi, E-86 Journal of Chemistry, 2012, 9(1), 167-170,.
[11]
George, B.Papadopoulos, E. P. Heterocycles from N- ethoxy carbonyl thioamides.
[12]
L. S. Gadekar, B. R. Arbad, and M. K. Lande, Chin. Chem. Lett., 2010, 21, 1053.
[13]
D. W. Hein, R. J. Alheim, and J. J. Leavitt, J. Am. Chem. Soc., 1957, 79, 427.
[14]
L. M. Schwartz, R. I. Gelb, Anal. Chem., 1978, 50, 1592.
[15]
G. Lente, I. Fabian, A. J. Poe New J. Chem. 2005, 29, 759.
[16]
J. H. Espenson, in chemical kinetics and mechanisms, McGraw-Hill, New York, 1995, 2 nd edn. 158.
[17]
A. J. Poe. In mechanisms of Inorganic and Organometallic Reaction , ed. M.V. Twigg, Plenum Prss, New York, 1994 8, ch. 10, 220.
