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Mechanistic investigation of oxidation of metronidazole and tinidazole with N -bromosuccinimide in acid medium: A kinetic approach
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2009 , DOI: 10.1007/bf03245835
K. N. Mohana , P. M. Ramdas Bhandarkar

Metronidazole (MTZ) and tinidazole (TNZ) belong to nitroimidazole group of drugs used to treat infections such as ameobiasis, giardiasis and trichomoniasis. The kinetics of oxidation of MTZ and TNZ with N-bromosuccinimide (NBS) in perchloric acid medium has been investigated at 308 K. A 1:1 stoichiometry has been observed in both MTZ and TNZ cases. The oxidation reactions of both MTZ and TNZ follow the same rate law, -d[NBS]/dt = [NBS][Sub][H+]. However, in case of MTZ, at higher concentrations of H+ (0.006–0.01 mol dm−3), the rate law obtained is -d[NBS]/dt = [NBS][MTZ][H+]−1. Accelerating effect of [Cl-] and retardation of the added succinimide on the reaction rate have been observed in the case of MTZ. The reactions were examined with reference to changes in concentration of added neutral salt, ionic strength and dielectric permittivity of the medium. The overall activation parameters have been evaluated from the Arrhenius plot. The reactive oxidizing species of NBS have been determined. The main oxidation products were identified by IR and 1H NMR spectral analyses. The observed results have been explained by plausible mechanisms and the relative rate laws have been deduced.

中文翻译:

N-溴代琥珀酰亚胺在酸性介质中氧化甲硝唑和替硝唑的机理研究:动力学方法

甲硝唑(MTZ)和替硝唑(TNZ)属于硝基咪唑类药物,用于治疗诸如氨弹病,贾第鞭毛虫病和滴虫病等感染。已在308 K下研究了N-溴琥珀酰亚胺(NBS)在N-溴代琥珀酰亚胺(NBS)中对MTZ和TNZ的氧化动力学。在MTZ和TNZ情况下均观察到1:1的化学计量。MTZ和TNZ的氧化反应均遵循相同的速率定律-d [NBS] / dt = [NBS] [Sub] [H + ]。但是,在MTZ的情况下,在更高的H +(0.006-0.01 mol dm -3)浓度下,获得的速率定律是-d [NBS] / dt = [NBS] [MTZ] [H + ] -1。加速的氯[Cl效果-在MTZ的情况下,已经观察到[α]和添加的琥珀酰亚胺对反应速率的延迟。参考添加的中性盐的浓度,离子强度和介质的介电常数的变化检查反应。总体激活参数已根据Arrhenius图进行了评估。已经确定了NBS的反应性氧化物质。通过IR和1 H NMR光谱分析鉴定了主要的氧化产物。观察到的结果已通过合理的机制进行了解释,并推导了相对速率定律。
更新日期:2020-09-12
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