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首页> 外文期刊>Journal of the Brazilian Chemical Society >Kinetics and mechanism of oxidation of the drug intermediate 1-(2-Hydroxyethyl)piperidine by Bis(hydrogenperiodato)argentate(III)
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Kinetics and mechanism of oxidation of the drug intermediate 1-(2-Hydroxyethyl)piperidine by Bis(hydrogenperiodato)argentate(III)

机译：双（氢过碘酸）银（III）氧化药物中间体1-（2-羟乙基）哌啶的动力学和机理

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摘要

1-(2-Hydroxyethyl)piperidine (HEP) is involved in many drugs and drug leads, but its oxidation mechanisms are poorly understood. The oxidation of HEP by bis(hydrogenperiodato)-argentate(III) ([Ag(HIO6)2]5-;) in aqueous alkaline medium was shown, by electrospray ionization mass spectrometry (ESI-MS), to generate piperidine and formaldehyde as the major products. The reaction was monitored spectrophotometrically in the 25.0 to 40.0 oC range revealing that the oxidation followed a first-order kinetics in [Ag(III)] and a fractional-order in [HEP]. A rate law and a reaction mechanism were proposed based on the study of the dependency of the pseudo-first-order rate constants, k obsd, on [OHˉ] and on [IO4ˉ]tot (total concentration of periodate). The mechanism involves the formation of a periodato-Ag(III)-HEP ternary complex, whose decomposition generates Ag(I) by means of two pathways: one independent and another facilitated by OHˉ. The reaction rate constants and associated equilibrium constants as well as the activation parameters of the rate-determining steps were calculated.
机译：1-（2-羟乙基）哌啶（HEP）与许多药物和药物先导有关，但对其氧化机理了解甚少。通过电喷雾电离质谱法（ESI-MS）显示，在碱性水溶液中，双（氢过碘酸）-银（III）（[Ag（HIO6）2] 5- ;;）对HEP的氧化生成了哌啶和甲醛，主要产品。在25.0至40.0 oC的范围内用分光光度法监测反应，结果表明，氧化反应遵循[Ag（III）]中的一级动力学，而遵循[HEP]中的分数级动力学。在研究伪一阶速率常数k obsd对[OHˉ]和[IO4ˉ] tot（高碘酸盐总浓度）的依赖性的基础上，提出了速率定律和反应机理。该机制涉及形成高碘酸盐-Ag（III）-HEP三元复合物，其分解通过两种途径生成Ag（I）：一种途径独立，另一种途径由OH 3促进。计算反应速率常数和相关的平衡常数，以及速率确定步骤的活化参数。

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