iodomalonic acid | 84695-78-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: iodomalonic acid
• 英文别名: IMA；2-iodopropanedioic acid
• CAS: 84695-78-3
• 化学式: C₃H₃IO₄
• 分子量: 229.959
• InChiKey: KPPZMQVVJYLLJL-UHFFFAOYSA-N

物化性质

• 沸点：
  384.3±37.0 °C(Predicted)
• 密度：
  2.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iodomalonic acid 在 sodium hydrogen sulfate 、 硫酸 、 potassium iodide 作用下， 以 水 为溶剂， 生成 丙二酸
  参考文献：
  名称：

  Photo-induced disproportionation of iodomalonic acid

  摘要：

  AbstractThe stoichiometry, equilibrium, and kinetics of the photo‐induced disproportionation of iodomalonic acid to I−, I2, and tartronic acid have been studied by means of spectrophotometry and iodide selective electrode at 20.0 ± 0.2°C, pH 2.0–4.0. At pH > 2.9, only I− and HOCH(COOH)2 are detected as major products and the reaction reaches 100% conversion. At pH < 2.9, I2 and malonic acid are also formed and the reaction stops at a conversion rate less than 100%. Both UV (band with a peak at 360 nm) and visible light (480 nm) have been found to be effective. Two primary photochemical processes are identified: equation image equation image While both reactions are sensitive to UV light, only (M2) can be affected by visible light. (M1) and (M2) are considered to initiate a chain reaction sequence in which I· radicals oxidize iodomalonic acid. Dual effects of reaction products on the reaction rate have been observed: while iodine increases the efficiency of visible light and accelerates the reaction, malonic acid inhibits the photo‐decomposition by mediating the recombination of I· radicals to I2. © 1995 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550270503
• 作为产物：
  描述：

  丙二酸 在 高氯酸 、 碘 作用下， 以 水 为溶剂， 生成 iodomalonic acid
  参考文献：
  名称：

  丙二酸衍生的烯醇作为亚硝化和卤化的中间体

  摘要：

  丙二酸，甲基丙二酸，乙基丙二酸和苯基丙二酸通过其相应的烯醇或烯醇化物形式与亲电子亚硝化剂以及与溴和碘反应。在大多数情况下，它可以使任一enolisation或烯醇限速由反应物浓度和反应性的适当选择的反应。烯醇化速率常数与存在的文献值相当吻合。我们建议K E的最小数字分别为1.0×10 -8和1.6×10 -8丙二酸和甲基丙二酸的烯醇化平衡常数。已显示[丙二酸]或其衍生物中的动力学术语二阶（当烯醇化是限速时）是由丙二酸根离子引起的碱催化组分引起的反应引起的，该丙二酸根离子在pH值大于ca时起主导作用。3。

  DOI：

  10.1016/s0040-4020(01)80471-3

文献信息

• Experimental and modeling study of oscillations in the chlorine dioxide-iodine-malonic acid reaction
  作者：Istvan Lengyel、Gyula Rabai、Irving R. Epstein

  DOI：10.1021/ja00181a011

  日期：1990.12

  an aqueous mixture of chlorine dioxide, iodine, and a species such as malonic acid (MA) or cthyl acetoacetate, which reacts with iodine to produce iodide, shows periodic changes in the light absorbance of I;. This behavior can be modeled by a simple scheme consisting of three component reactions: (I) the reaction between MA and iodine, which serves as a continuous source of I-; (2) the reaction between

  在 pH 值 0.5-5.0 时，包含二氧化氯、碘和丙二酸 (MA) 或乙酰乙酸乙酯等物质的含水混合物的封闭系统，可与碘反应生成碘化物，I 的光吸收率显示周期性变化;. 这种行为可以通过由三个组分反应组成的简单方案进行建模：(I) MA 和碘之间的反应，作为 I- 的连续来源；(2) ClO,' 和 I- 之间的反应，作为 C102- 的来源：和 (3) 亚氯酸盐和碘化物的自抑制反应，动力学调节系统。用停流分光光度法研究了快速组分反应 bctwccn 二氧化氯和碘离子。速率定律是 -(C102')/df = 6 X IO3 (M-2 s-')(CIO,')(I-)。从三组分反应的经验速率定律获得的二变量模型很好地描述了系统的动力学。振荡行为不是由自催化引起的，而是由亚氯酸盐-碘化物反应的自抑制特性引起的。
• Experimental and Mechanistic Investigation of an Iodomalonic Acid-Based Briggs−Rauscher Oscillator and its Perturbations by Resorcinol
  作者：Rinaldo Cervellati、Emanuela Greco、Stanley D. Furrow

  DOI：10.1021/jp108684d

  日期：2010.12.16

  Classic Briggs−Rauscher oscillators use malonic acid (MA) as a substrate. The first organic product is iodomalonic acid. Iodomalonic acid (IMA) can serve as a substrate also; thus, the first product in that case is diiodomalonic acid (I2MA). Nonoscillating iodination kinetics can be followed by absorbance at 462 nm in acidic KIO3 so long as IMA is in substantial excess over [I2]. At 25 °C, simulations

  经典的Briggs-Rauscher振荡器使用丙二酸（MA）作为基质。第一种有机产物是碘doMAloniconic acid。碘丙二酸（IMA）也可以用作底物；因此，在这种情况下，第一产物是二碘代丙二酸（I 2 MA）。只要IMA大大超过[I 2 ]，在酸性KIO 3中，非振荡碘化动力学可以跟随在462 nm处的吸光度。在25°C下，模拟得出两个最重要的速率定律，并报告了相关的速率常数估算值。I 2 MA最终会通过未知过程分解，但I 2，O 2，H 2 O 2和Mn 2+加快分解速度，将大部分碘释放回溶液中。间苯二酚是MA振荡器和IMA振荡器中振荡的有效抑制剂。本文显示了IMA振荡器对间苯二酚含量变化的响应，与基于MA的振荡器的响应相似。通过将IMA添加到基于MA的振荡器中，间苯二酚的抑制作用会减弱。IMA和间苯二酚之间的碘化反应太慢（0.043 M -1 s -1），不足以说明间苯二酚的抑制效果降低。相反，I
• TheBriggs-Rauscher Reaction as a Test to Measure the Activity of Antioxidants
  作者：Rinaldo Cervellati、Kerstin Höner、Stanley D. Furrow、Christina Neddens、Stefano Costa

  DOI：10.1002/1522-2675(20011219)84:12<3533::aid-hlca3533>3.0.co;2-y

  日期：2001.12.19

  oscillations of the Briggs-Rauscher reaction. The effect consists of an immediate cessation of oscillations, an inhibition time that linearly depends on the concentration of the antioxidant added, and subsequent regeneration of oscillations. Here the effects of ten antioxidants (pyrocatechol (=benzene-1,2-diol), ferulic acid (=3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid), caffeic acid (=3-(3,4-dihyd

  提出了一种监测抗氧化剂相对活性的新方法，并讨论了其优点和局限性。该方法基于先前报道的自由基清除剂对 Briggs-Rauscher 反应振荡的抑制作用。效果包括立即停止振荡、线性取决于添加的抗氧化剂浓度的抑制时间以及随后的振荡再生。这里有十种抗氧化剂（邻苯二酚（=苯-1,2-二醇）、阿魏酸（=3-（4-羟基-3-甲氧基苯基）丙-2-烯酸）、咖啡酸（=3-（3 ,4-二羟基苯基)丙-2-烯酸)、2,6-、3,4-、2,4-、3,5- 和 2,5-二羟基苯甲酸、高香草酸 (=4-羟基-3 -甲氧基苯乙酸）和间苯二酚（=苯-1,3-二醇））进行了详细研究。这些物质对间苯二酚的相对抗氧化活性根据抑制时间以不同方式确定。基于 Briggs-Rauscher 反应的相对活性计算值的限制与使用其他分析程序获得的限制相同，并在此讨论。新方法价格低廉：所有化学实验室都普遍使用试剂和仪器。还仔细研究并考虑了 Briggs-Rauscher
• Modelling flow-distributed oscillations in the CDIMA reaction
  作者：Jonathan R. Bamforth、Serafim Kalliadasis、John H. Merkin、Stephen K. Scott

  DOI：10.1039/b004552g

  日期：——

  The development of spatial patterns (‘flow distributed oscillations’) in a model representing the chlorine dioxide–iodine–malonic acid (CDIMA) reaction is investigated analytically and numerically. Flow distributed oscillations arise in a plug-flow reactor (PFR) for which the inflow concentrations of the various reacting species are maintained at appropriate constant values. Unlike other situations, the patterning here does not require any difference in diffusion coefficients for the different species. The patterns are, however, closely related to operating conditions for which the same chemical system would show temporal oscillations in a well-stirred batch reactor. As the flow rate through the PFR is varied, the system undergoes a sequence of transitions from absolute to convective instability and subsequently to stationary patterns. The onset of stationary patterns is found to be subcritical, so there is a range of operating conditions for which there is bistability between a stationary pattern and an essentially uniform state. The results indicate that these patterns occur for conditions that should be realisable experimentally and that typical wavelengths of the patterns would be of the order of 0.1 mm.

  本研究通过分析和数值方法研究了二氧氯-碘-丙二酸（CDIMA）反应模型中空间模式（"流动分布振荡"）的发展。流动分布振荡产生于塞流反应器（PFR）中，在该反应器中，各种反应物的流入浓度保持在适当的恒定值。与其他情况不同的是，这里的模式不要求不同物种的扩散系数存在任何差异。不过，这种模式与操作条件密切相关，在搅拌良好的间歇式反应器中，相同的化学系统会出现时间振荡。随着通过并流式反应器的流速变化，系统会经历从绝对不稳定到对流不稳定，再到静止模式的一系列转变。研究发现，静止模式的开始是亚临界状态，因此在一定范围的运行条件下，静止模式和基本均匀状态之间存在双稳态。结果表明，这些模式出现的条件应该可以在实验中实现，模式的典型波长为 0.1 毫米。
• Comparison of Several Substrates in the Briggs-Rauscher Oscillating System
  作者：Stanley D. Furrow

  DOI：10.1021/j100028a013

  日期：1995.7

  Acetone, methylmalonic acid, malonic acid, iodomalonic acid, and phenylmalonic acid are compared under identical conditions in the Briggs-Rauscher oscillating System. Each of these five substrates consumes iodine to form an iodo product and produces iodide at the same time. The rates of iodine consumption have been measured for each of the substrates individually. To a first approximation, all of the substrates behave in a similar manner when compared at concentrations which react with iodine at similar rates. A skeleton model for the oscillatory system cannot quantitatively-predict variations of the oscillatory period with concentration for any one of the substrates. Several reactions and processes are discussed which must be part of a complete description of the oscillator but which make only;marginal improvements when compared to the skeleton model: reduction of iodate ion and iodine by hydroperoxy radical, reduction of iodate by the substrate enol, second-order reduction of iodate by iodide, net oxidation of iodine by hydrogen peroxide, continuous HOIO production, and decomposition of the iodo products.