Oxidative transformation of ciprofloxacin by alkaline permanganate – A kinetic and mechanistic study

Thabaj, Kiran A.; Kulkarni, Suresh D.; Chimatadar, Shivamurti A.; Nandibewoor, Sharanappa T.

doi:10.1016/j.poly.2007.06.030

Cited by 41 publications

(24 citation statements)

References 34 publications

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“…The value of K 1 (9.38 L mol -1 ) is in good agreement with that derived in earlier work 33 (literature value is 9.3 L mol -1 at 30°C). Van't Hoff's plot of log K 1 versus 1/T give the values of enthalpy of reaction ΔH, entropy of reaction ΔS and free energy of reaction ΔG ( Table 2).…”

Section: Discussionsupporting

confidence: 91%

“…The m/z 263 corresponds to full dealkylation of the piperazine ring and classified as (M -69) product because of its structural similarity to the (M -69) product of ciprofloxacin. 33 However, the product does not have the same mass loss of 69 from the parent molecule. This product was also identified previously as oxidation product of enrofloxacin.…”

Section: Stoichiometry and Product Analysismentioning

confidence: 99%

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Kinetics and Mechanism of Permanganate Oxidation of Enrofloxacin in Aqueous Alkaline Medium

Jain¹,

Devra²

2017

J. Pharm. Sci. Innov.

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The reaction kinetics of oxidation of enrofloxacin by potassium permanganate has been investigated in aqueous alkaline medium using spectrophotometric technique at 30 ± 1°C at constant ionic strength of 0.10 mol L -1 . The reaction exhibits 2:1 stoichiometry (2 KMnO4:1 Enrofloxacin). The order with respect to oxidant and substrate is found to be unity in each, whereas fractional order with re spect to alkali concentration. The oxidation products were identified by using FTIR, LCMS spectral studies. The effects of added products, ionic strength and dielectric constant have been studied on the rate of reaction. Based on the experimental results a suitable mechanism is proposed. There is no evidence of intermediate complex formation, thus, the outer-sphere mechanism is proposed as the mechanism for this reaction.

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Section: Discussionsupporting

confidence: 91%

Section: Stoichiometry and Product Analysismentioning

confidence: 99%

Kinetics and Mechanism of Permanganate Oxidation of Enrofloxacin in Aqueous Alkaline Medium

Jain¹,

Devra²

2017

J. Pharm. Sci. Innov.

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“…These results imply that first the alkali combines with permanganate to give an alkali-permanganate species [MnO 4 .OH] 2-in a prior equilibrium step, which is in accordance with the literature [14] and also the observed order with respect to OH -. In the next step, [MnO 4 .OH] 2-combines with panthenol to form an intermediate complex (C 1 ).…”

Section: Mechanism For the Uncatalysed Reactionsupporting

confidence: 91%

Kinetics and mechanism of uncatalysed and ruthenium(III)-catalysed oxidation of d-panthenol by alkaline permanganate

Hosahalli

Savanur

Nandibewoor

et al. 2009

Transition Met Chem

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The oxidation of D-panthenol by MnO 4 -was studied in the absence and in the presence of ruthenium(III) catalyst in alkaline medium at 298 K and at constant ionic strength of 0.50 mol dm -3 by spectrophotometry. The stoichiometry in both the cases was [panthenol]: [MnO 4 -] = 1:4. The oxidation products were identified by IR and GC-MS. The reaction was first-order with respect to both MnO 4 -and ruthenium(III), while the orders with respect to both panthenol and alkali varied from first order to zero order as the concentrations increased. The effects of added products, ionic strength and dielectric constant were studied. The reaction constants, activation parameters and thermodynamic quantities were calculated for both the uncatalysed and catalysed reactions.

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“…This suggests that the initial products might have undergone further oxidation resulting in a lower oxidation state of manganese. It appears that the alkali combines with permanganate to give [MnO 4 ÁOH] 2- [32,33]. Ea (kJmole -1 ) 14.9 DH (kJmole -1 ) 11.9 DS ± (Jk -1 mole -1 ) -143.2 DG ± (kJmole -1 ) 63.10…”

Section: Discussionmentioning

confidence: 99%

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

Khan

Mohd

Bano

et al. 2009

Transition Met Chem

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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.

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Oxidative transformation of ciprofloxacin by alkaline permanganate – A kinetic and mechanistic study

Cited by 41 publications

References 34 publications

Kinetics and Mechanism of Permanganate Oxidation of Enrofloxacin in Aqueous Alkaline Medium

Kinetics and Mechanism of Permanganate Oxidation of Enrofloxacin in Aqueous Alkaline Medium

Kinetics and mechanism of uncatalysed and ruthenium(III)-catalysed oxidation of d-panthenol by alkaline permanganate

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

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