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Kinetics and Mechanism of Oxidation of Chalcones by 1,3-Dichloro-5,5-dimethyl Hydantoin
Corresponding Author(s) : K. Karunakaran
Asian Journal of Chemistry,
Vol. 27 No. 5 (2015): Vol 27 Issue 5
Abstract
Mechanistic study on oxidation of chalcone by 1,3-dichloro-5,5-dimethyl hydantoin (DCDMH or DCH) in aqueous acetic acid medium have been carried out. The reaction follows a fractional order (0.63) with respect to substrate and first order with respect to the oxidant. Increase in percentage of acetic acid increased the rate of the reaction. The added H+ did not affect the reaction rate. The oxidation reaction fails to initiate polymerization with acrylonitrile and free radical mechanism is ruled out. The thermodynamic and activation parameters for the oxidation have been determined and discussed. Based on the observations a probable mechanism and rate law were proposed.
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- M.A. Rahman, Chem. Sci. J., 29, 1 (2011).
- S.S. Lim, H.S. Kim and D.U. Lee, Bull. Korean Chem. Soc., 28, 2495 (2007).
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- H.L. Yadav, P. Gupta, P.S. Pawar, P.K. Singour and U.K. Patil, Med. Chem. Res., 20, 461 (2011).
- P.M. Sivakumar, P.K. Prabhakar and M. Doble, Med. Chem. Res., 20, 482 (2011).
- D.D. Sung and A. Nadar, Bull. Korean Chem. Soc., 20, 1487 (1999).
- J. Anilkumar and S. Sondu, Indian J. Chem., 46A, 1792 (2007).
- N.C. Khandual, K.K. Satpathy and P.L. Nayak, J. Chem. Soc. Perkin II, 328 (1974).
- B. Kuotsu, E. Tiewsoh, A. Debroy and M.K. Mahanti, J. Org. Chem., 61, 8875 (1996).
- S.P. Vaijayanthi and N. Mathiyalagan, J. Chem. Biol. Phys. Sci., 2, 1281 (2012).
- S.P. Vaijayanthi and N. Mathiyalagan, Int. J. Res. Pharm. Chem., 2, 722 (2012).
- K.G. Sekar and S.K. Periyasami, J. Chem. Pharm. Res., 4, 2153 (2012).
- E. Kolvari, A. Ghorbani-Choghamarani, P. Salehi, F. Shirini and M.A. Zolfigol, J. Iran. Chem. Soc., 4, 126 (2007).
- J. Mukherjee and K.K. Banerji, J. Org. Chem., 46, 2323 (1981).
- A.K. Singh, V. Singh, S. Rahmani, A.K. Singh and B. Singh, J. Mol. Catal. A, 197, 91 (2003).
- R. Filler, Chem. Rev., 63, 21 (1963).
- P.V. Balasubramaniyan and N. Mathiyalagan, J. Chem. Pharm. Res., 3, 522 (2011).
- N.S. Srinivasan and N. Venkatasubramanian, Tetrahedron Lett., 11, 2039 (1970).
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References
M.A. Rahman, Chem. Sci. J., 29, 1 (2011).
S.S. Lim, H.S. Kim and D.U. Lee, Bull. Korean Chem. Soc., 28, 2495 (2007).
R.J. Anto, K. Sukumaran, G. Kuttan, M.N.A. Rao, V. Subbaraju and R. Kuttan, Cancer Lett., 97, 33 (1995).
J. Vaya, A.P. Belinky and M. Aviram, Free Radic. Biol. Med., 23, 302 (1997).
H.L. Yadav, P. Gupta, P.S. Pawar, P.K. Singour and U.K. Patil, Med. Chem. Res., 20, 461 (2011).
P.M. Sivakumar, P.K. Prabhakar and M. Doble, Med. Chem. Res., 20, 482 (2011).
D.D. Sung and A. Nadar, Bull. Korean Chem. Soc., 20, 1487 (1999).
J. Anilkumar and S. Sondu, Indian J. Chem., 46A, 1792 (2007).
N.C. Khandual, K.K. Satpathy and P.L. Nayak, J. Chem. Soc. Perkin II, 328 (1974).
B. Kuotsu, E. Tiewsoh, A. Debroy and M.K. Mahanti, J. Org. Chem., 61, 8875 (1996).
S.P. Vaijayanthi and N. Mathiyalagan, J. Chem. Biol. Phys. Sci., 2, 1281 (2012).
S.P. Vaijayanthi and N. Mathiyalagan, Int. J. Res. Pharm. Chem., 2, 722 (2012).
K.G. Sekar and S.K. Periyasami, J. Chem. Pharm. Res., 4, 2153 (2012).
E. Kolvari, A. Ghorbani-Choghamarani, P. Salehi, F. Shirini and M.A. Zolfigol, J. Iran. Chem. Soc., 4, 126 (2007).
J. Mukherjee and K.K. Banerji, J. Org. Chem., 46, 2323 (1981).
A.K. Singh, V. Singh, S. Rahmani, A.K. Singh and B. Singh, J. Mol. Catal. A, 197, 91 (2003).
R. Filler, Chem. Rev., 63, 21 (1963).
P.V. Balasubramaniyan and N. Mathiyalagan, J. Chem. Pharm. Res., 3, 522 (2011).
N.S. Srinivasan and N. Venkatasubramanian, Tetrahedron Lett., 11, 2039 (1970).
K. Vivekanandan and K. Nambi, J. Indian Chem. Soc., 76, 198 (1999)