Kinetic and mechanistic investigation of the oxidation of the antibacterial agent levofloxacin by permanganate in alkaline medium

The kinetics and mechanism of oxidation of levofloxacin (LF) by manganese(VII) in alkaline medium at constant ionic strength was studied spectrophotometrically. The reaction exhibits 2:1 Mn:LF stoichiometry and is first order in permanganate but fractional order in both LF and alkali. Decrease in the dielectric constant of the medium results in a decrease in the rate of reaction. The effects of added products and ionic strength have also been investigated. The main products identified were hydroxylated LF and Mn(VI). A mechanism involving free radicals is proposed. In a composite equilibrium step, levofloxacin binds to MnO 4 − to form a complex that subsequently decomposes to the products. Investigations of the reaction at different temperatures allowed the determination of the activation parameters with respect to the slow step of the proposed mechanism.