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首页> 外文期刊>Polyhedron: The International Journal for Inorganic and Organometallic Chemistry >Oxidative transformation of ciprofloxacin by alkaline permanganate - A kinetic and mechanistic study
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Oxidative transformation of ciprofloxacin by alkaline permanganate - A kinetic and mechanistic study

机译：碱性高锰酸盐对环丙沙星的氧化转化-动力学和机理研究

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摘要

This spectroscopic study presents the kinetics and degradation pathways of oxidation of ciprofloxacin by permanganate in alkaline medium at constant ionic strength of 0.04 mol(-3), Orders with respect to substrate, oxidant and alkali concentrations were determined. Effect of ionic strength and solvent polarity of the medium on the rate of the reaction was studied. The oxidation products were identified by LC-ESI-MS technique. Product characterization of ciprofloxacin reaction mixtures indicates the formation of three major products corresponding to m/z 263, 306, and 348 (corresponding to full or partial dealkylation of the piperazine ring). The piperazine moiety of ciprofloxacin is the predominant oxidative site to KMnO4. Product analyses showed that oxidation by permanganate results in dealkylation at the piperazine moiety of ciprofloxacin, with the quinolone ring essentially intact. The reaction kinetics and product characterization point to a reaction mechanism that likely begins with formation of a complex between ciproffoxacin and the KMnO4, followed by oxidation at the aromatic N1 atom of piperazine moiety to generate an anilinyl radical intermediate. The radical intermediates subsequently undergo N-dealkylation. Investigations of the reaction at different temperatures allowed the determination of the activation parameters with respect to the slow step of proposed mechanism. The proposed mechanism and the derived rate laws are consistent with the observed kinetics. (C) 2007 Elsevier Ltd. All rights reserved.
机译：该光谱研究显示了高锰酸盐在碱性介质中以0.04 mol（-3）恒定的离子强度氧化环丙沙星的动力学和降解途径，确定了有关底物，氧化剂和碱浓度的顺序。研究了介质的离子强度和溶剂极性对反应速率的影响。氧化产物通过LC-ESI-MS技术鉴定。环丙沙星反应混合物的产物表征表明形成了三种对应于m / z 263、306和348的主要产物（对应于哌嗪环的全部或部分脱烷基）。环丙沙星的哌嗪部分是KMnO4的主要氧化位点。产物分析表明，高锰酸盐的氧化导致环丙沙星哌嗪部分的去烷基化，喹诺酮环基本完好无损。反应动力学和产物表征指向一种反应机理，该机理可能始于西泊沙星与KMnO4之间的络合物的形成，然后在哌嗪部分的芳族N1原子处氧化生成苯胺基自由基中间体。自由基中间体随后进行N-脱烷基。在不同温度下对反应的研究使得可以相对于所提出的机理的缓慢步骤来确定活化参数。所提出的机理和导出的速率定律与观察到的动力学一致。 （C）2007 Elsevier Ltd.保留所有权利。

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