Experimental and theoretical studies on the oxidation of lomefloxacin by alkaline permanganate

Kulkarni, Raviraj M.; Hanagadakar, Manjunath S.; Malladi, Ramesh S.; Biswal, Himansu S.; Cuerda-Correa, Eduardo M.

doi:10.1080/19443994.2015.1037797

Cited by 12 publications

(5 citation statements)

References 36 publications

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“…For both uncatalyzed and catalyzed reactions, the possible interference of free radicals was examined by adding acrylonitrile to the reaction mixture. It was stored in an inert environment for 24 h. This reaction mixture was diluted by methyl alcohol, and precipitate was not observed, which suggests that free radicals were not involved in the reaction .…”

Section: Resultsmentioning

confidence: 99%

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Ag(I)‐Catalyzed Chlorination of Linezolid during Water Treatment: Kinetics and Mechanism

Kulkarni

Hanagadakar

Malladi

et al. 2018

Int J of Chemical Kinetics

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The kinetic and mechanistic study of Ag(I)‐catalyzed chlorination of linezolid (LNZ) by free available chlorine (FAC) was investigated at environmentally relevant pH 4.0–9.0. Apparent second‐order rate constants decreased with an increase in pH of the reaction mixture. The apparent second‐order rate constant for uncatalyzed reaction, e.g., k″app = 8.15 dm3 mol−1 s−1 at pH 4.0 and k″app. = 0.076 dm3 mol−1 s−1 at pH 9.0 and 25 ± 0.2°C and for Ag(I) catalyzed reaction total apparent second‐order rate constant, e.g., k″app = 51.50 dm3 mol−1 s−1 at pH 4.0 and k″app. = 1.03 dm3 mol−1 s−1 at pH 9.0 and 25 ± 0.2°C. The Ag(I) catalyst accelerates the reaction of LNZ with FAC by 10‐fold. A mechanism involving electrophilic halogenation has been proposed based on the kinetic data and LC/ESI/MS spectra. The influence of temperature on the rate of reaction was studied; the rate constants were found to increase with an increase in temperature. The thermodynamic activation parameters Ea, ΔH#, ΔS#, and ΔG# were evaluated for the reaction and discussed. The influence of catalyst, initially added product, dielectric constant, and ionic strength on the rate of reaction was also investigated. The monochlorinated substituted product along with degraded one was formed by the reaction of LNZ with FAC.

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Section: Resultsmentioning

confidence: 99%

“…HOCl is the predominant species below pH 7.5 and OCl − is predominant above pH 7.5. The decrease in the magnitude of k ″ app above pH 7.5 can be attributed to deprotonation of HOCl to yield OCl − , that is generally a much weaker electrophile than HOCl; for this reason HOCl has been considered as the reactive species .…”

Section: Resultsmentioning

confidence: 99%

Ag(I)‐Catalyzed Chlorination of Linezolid during Water Treatment: Kinetics and Mechanism

Kulkarni

Hanagadakar

Malladi

et al. 2018

Int J of Chemical Kinetics

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“…In addition, the bactericidal action of LOM and BAL results from the inhibition of topoisomerase IV, which is needed for the transcription and replication of bacterial DNA [ 24 ]. The degradation studies on LOM have been performed while using different oxidation agents: H 2 O 2 /UV, alkaline permanganate, permanganate in acidic medium and catalytically activated persulfate, in few cases the degradation products were separated and identified by LC-MS [ 25 , 26 , 27 , 28 ]. In the available literature, there is no information regarding hydroxyl-radical induced oxidation of BAL or in the presence of H 2 O 2 , although several studies are focused on its photooxidation process [ 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Development and Validation of Stability-Indicating HPLC Methods for the Estimation of Lomefloxacin and Balofloxacin Oxidation Process under ACVA, H2O2, or KMnO4 Treatment. Kinetic Evaluation and Identification of Degradation Products by Mass Spectrometry

et al. 2020

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The oxidation of lomefloxacin (LOM) and balofloxacin (BAL) under the influence of azo initiator of radical reactions of 4,4′-azobis(4-cyanopentanoic acid) (ACVA) and H2O2 was examined. Oxidation using H2O2 was performed at room temperature while using ACVA at temperatures: 40, 50, 60 °C. Additionally, the oxidation process of BAL under the influence of KMnO4 in an acidic medium was investigated. New stability-indicating HPLC methods were developed in order to evaluate the oxidation process. Chromatographic analysis was carried out using the Kinetex 5u XB—C18 100A column, Phenomenex (Torrance, CA, USA) (250 × 4.6 mm, 5 μm particle size, core shell type). The chromatographic separation was achieved while using isocratic elution and a mobile phase with the composition of 0.05 M phosphate buffer (pH = 3.20 adjusted with o-phosphoric acid) and acetonitrile (87:13 v/v for LOM; 80:20 v/v for BAL). The column was maintained at 30 °C. The methods were validated according to the ICH guidelines, and it was found that they met the acceptance criteria. An oxidation process followed kinetics of the second order reaction. The most probable structures of LOM and BAL degradation products formed were assigned by the UHPLC/MS/MS method.

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“…Recent research has verified the presence of numerous antibacterial compounds in the aquatic environment . These antibacterial compounds have emerged as a new class of pollutants because of their adverse effects on human health . The oxidative transformation of fluoroquinolone antibacterial agents in a water treatment process definitely plays a major role in this concern.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Ciprofloxacin by Hexacyanoferrate(III) in the Presence of Cu(II) as a Catalyst: A Kinetic Study

Tazwar¹,

Jain²,

Mittal³

et al. 2017

Int. J. Chem. Kinet.

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The Cu(II)‐catalyzed oxidation of ciprofloxacin (CIP) by hexacyanoferrate(III) (HCF) has been investigated spectrophotometrically in an aqueous alkaline medium at 40°C. The stoichiometry for the reaction indicates that the oxidation of 1 mol of CIP requires 2 mol of HCF. The reaction exhibited first‐order kinetics with respect to [HCF] and less than unit order with respect to [CIP] and [OH−]. The products were also identified on the basis of stoichiometric results and confirmed by the characterization results of LC‐MS and FT‐IR analysis. All the possible reactive species of the reactants have been discussed, and a most probable kinetic model has been envisaged. The activation parameters with respect to the slow step of the mechanism were computed, and thermodynamic quantities were also determined.

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Experimental and theoretical studies on the oxidation of lomefloxacin by alkaline permanganate

Cited by 12 publications

References 36 publications

Ag(I)‐Catalyzed Chlorination of Linezolid during Water Treatment: Kinetics and Mechanism

Ag(I)‐Catalyzed Chlorination of Linezolid during Water Treatment: Kinetics and Mechanism

Development and Validation of Stability-Indicating HPLC Methods for the Estimation of Lomefloxacin and Balofloxacin Oxidation Process under ACVA, H2O2, or KMnO4 Treatment. Kinetic Evaluation and Identification of Degradation Products by Mass Spectrometry

Oxidation of Ciprofloxacin by Hexacyanoferrate(III) in the Presence of Cu(II) as a Catalyst: A Kinetic Study

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