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http://dx.doi.org/10.5012/bkcs.2012.33.11.3544

Kinetic and Mechanistic Studies of Oxidation of an Antiallergic Drug with Bromamine-T in Acid and Alkaline Media  

Puttaswamy, Puttaswamy (Department of Post-Graduate Studies in Chemistry, Bangalore University, Central College Campus)
Sukhdev, Anu (Department of Post-Graduate Studies in Chemistry, Bangalore University, Central College Campus)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.11, 2012 , pp. 3544-3550 More about this Journal
Abstract
Cetrizine dihydrochloride (CTZH) is widely used as an anti-allergic drug. Sodium N-bromo-p-toluenesulfonamide or bromamine-T (BAT) is the bromine analogue of chloramine-T (CAT) and is found to be a better oxidizing agent than CAT. In the present research, the kinetics of oxidation of CTZH with BAT in acid and alkaline media was studied at 313 K. The experimental rate laws obtained are: -d[BAT]/dt=$k[BAT][CTZH]^{0.80}[H^+]^{-0.48}$ in acid medium and -d[BAT]/dt=$k[BAT][CTZH]^{0.48}[OH^-]^{0.52}[PTS]^{-0.40}$ in alkaline medium where PTS is p-toluenesulfonamide. Activation parameters and reaction constants were evaluated. The solvent isotope effect was studied using $D_2O$. The dielectric effect is positive. The stoichiometry of the reaction was found to be 1:1 and the oxidation products were identified as 4-chlorobenzophenone and (2-piperazin-1-yl-ethoxy)-acetic acid in both media. The rate of oxidation of CTZH is faster in acid medium. Suitable mechanisms and related rate laws have been worked out.
Keywords
Cetrizine; Oxidation-kinetics; Bromamine-T; Acid and alkaline media;
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