paraquat dichloride | 1910-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: paraquat dichloride
• 英文别名: methyl viologen dichloride；paraquat；methyl viologen；1,1'-dimethyl-4,4'-bipyridinium dichloride；N,N'-dimethyl-4,4'-bipyridinium dichloride；1,1′-dimethyl-4,4′-bipyridinium dichloride；N,N’-dimethyl-4,4‘-bipyridinium dichloride；N,N′-dimethyl-4,4′-bipyridinium dichloride；1,1'-dimethyl-4,4'-bipyridinium chloride；methyl viologen chloride；1,1’-dimethyl-4,4’-bipyridinium dichloride；1,1′-dimethyl-4,4′-bipyridylium dichloride；N,N’-dimethyl-4,4’-bipyridinium dichloride；1,1'-dimethyl-4,4'-bipyridium dichloride；methyl viologen dichloride hydrate；dimethylviologen dichloride；viologen dichloride；1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium;chloride
• CAS: 1910-42-5
• 化学式: C₁₂H₁₄N₂*2Cl
• 分子量: 257.163
• InChiKey: PHBHFYCOBFRUKJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.99
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  7.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  paraquat dichloride 生成 methyl viologen cation radical
  参考文献：
  名称：

  Partition Parameters for Three Redox Forms of Viologen in a Nonionic Micellar Solution

  摘要：

  通过电化学方法测定了 1,1′-二甲基-4,4′-联吡啶鎓（1）、1-癸基-1′-甲基-4,4′-联吡啶鎓（2）和 1-十二烷基-1′-甲基-4,4′-联吡啶鎓（3）在胶束相和水相之间的分配参数。结果表明，10、2underset.+、20 和 32+ 几乎完全溶解在胶束相中，而 12+、1underset.+ 和 22+ 则分成两相。

  DOI：

  10.1246/bcsj.60.1521
• 作为产物：
  描述：

  methyl viologen cation radical 在 水 、 dioxide titanium 、 异丙醇 作用下， 生成 paraquat dichloride
  参考文献：
  名称：

  Photocatalytic Reduction of Nitroorganics over Illuminated Titanium Dioxide:  Electron Transfer between Excited-State TiO₂ and Nitroaromatics

  摘要：

  The present study investigates the steady-state photocatalytic reduction of methyl viologen and a suite of monosubstituted nitrobenzenes. Reduction was carried out in deoxygenated, illuminated aqueous slurries of titanium dioxide (Degussa P25) in the presence of a sacrificial electron donor, 2-propanol. Langmuir-Hinshelwood plots were obtained for the reduction of each compound and found to be linear, with an average correlation of 0.98 and with a standard deviation on the correlations of 0.02. The concentration independent rates for nitroaromatic reduction obtained from these plots were normalized against the rate of methyl viologen reduction, and the ratio was used to solve for the rate constant of nitroaromatic reduction, assuming a bimolecular model. The assumptions behind this procedure were tested by the use of the Marcus expression. Using the reorganization energy for the reaction as the fitting variable, it was possible to fit the measured rates to the predicted rates with a reorganization energy of 138 kJ/mol.

  DOI：

  10.1021/jp973224l
• 作为试剂：
  描述：

  四氯乙烯 在 reductive dehalogenase of Sulfurospirillum multivorans 、 paraquat dichloride 作用下， 以 various solvent(s) 为溶剂， 生成 顺-1,2-二氯乙烯
  参考文献：
  名称：

  Electroenzymatic Reactions. Investigation of a Reductive Dehalogenase by Means of Electrogenerated Redox Cosubstrates

  摘要：

  As an illustration of how cyclic voltammetry can be used to unravel the mechanisms and kinetics of redox enzymes, the reductive dechlorination of trichloroethylene and tetrachloroethylene by a typical reductive dehalogenase, the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans (formerly called Dehalospirillum multivorans), was investigated by means of several electrochemically generated cosubstrates. They comprised the monocation and the neutral form of methylviologen, the neutral form of benzylviologen, and cobaltocene. Cyclic voltammetry is used to produce the active form of the cosubstrate under controlled potential conditions. It shows large plateau-shaped catalytic responses, which are used to measure the kinetics of the enzymatic reaction as a function of the substrate and cosubstrate concentrations. The variation of the rate constant for the cosubstrate reaction with its standard potential shows the transition between two asymptotic behaviors, one in which the reaction is under diffusion control and the other in which it is under counter-diffusion control. Simple fitting of this plot allows an estimation of the standard potential of the electron acceptor center in the enzyme (E degrees = -0.57 V vs NHE).

  DOI：

  10.1021/ja053403d

文献信息

• Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
  作者：Henian Peng、Tiejun Li、Duanshuai Tian、He Yang、Guangqing Xu、Wenjun Tang

  DOI：10.1039/d1ob00300c

  日期：——

  A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from

  一系列不饱和羰基、醌和吡啶盐已被有效地还原为相应的饱和羰基、二羟基苯和氢吡啶，其中四羟基二硼/水是一种温和、方便且无金属的还原体系，其产率中等至高。氘标记实验表明，该协议是一种从水中进行的独家转移氢化过程。
• [2+2] Cycloadditions by Oxidative Visible Light Photocatalysis
  作者：Michael A. Ischay、Zhan Lu、Tehshik P. Yoon

  DOI：10.1021/ja103934y

  日期：2010.6.30

  cyclobutanes and other strained ring systems that are difficult to construct using other conventional synthetic methods. We have previously shown that Ru(bpy)(3)(2+) is an efficient photocatalyst that promotes the [2+2] cycloadditions of electron-deficient olefins with visible light. Here, we show that Ru(bpy)(3)(2+) is also an effective photocatalyst for the [2+2] cycloaddition of electron-rich olefins

  光化学反应因其能够轻松组装环丁烷和其他使用其他常规合成方法难以构建的应变环系统而著称。我们之前已经表明 Ru(bpy)(3)(2+) 是一种有效的光催化剂，可以促进缺电子烯烃在可见光下的 [2+2] 环加成反应。在这里，我们表明 Ru(bpy)(3)(2+) 也是富电子烯烃 [2+2] 环加成的有效光催化剂。这种转变是由 Ru(bpy)(3)(2+) 的多功能光电化学特性实现的，它可以在适当的条件下对感兴趣的有机底物进行单电子还原或单电子氧化。
• Proton-Coupled Electron Transfer in a Strongly Coupled Photosystem II-Inspired Chromophore–Imidazole–Phenol Complex: Stepwise Oxidation and Concerted Reduction
  作者：Gerald F. Manbeck、Etsuko Fujita、Javier J. Concepcion

  DOI：10.1021/jacs.6b03506

  日期：2016.9.14

  280 < HDA < 540 cm(-1) consistent with strong electronic coupling and slow solvent dynamics. Reduction of the phenoxyl radical by the quencher radical was examined as the analogue of the redox reaction between the PSII tyrosyl radical and the oxygen-evolving complex. In our PSII-inspired complex, the recombination reaction activation energy is <2 kcal mol(-1). The reaction is nonadiabatic (VPCET ≈ 22

  在乙腈中研究了质子耦合电子转移 (PCET) 反应，用于受光系统 II (PSII) 启发的 [Ru(bpy)2(phen-咪唑-Ph(OH)((t)Bu)2)](2+) ，其中由快速猝灭序列生成的 Ru(III) 氧化附加的苯酚，质子转移到氢键连接的咪唑碱。与相关系统相反，供体和受体是强耦合的，如苯酚氧化时 Ru(III/II) 对的位移所示，并且 Ru(III) 对苯酚的分子内氧化在能量上是有利的一致的途径。苯酚氧化通过逐步 ET-PT 机制发生，kET = 2.7 × 10(7) s(-1)，动力学同位素效应 (KIE) 为 0.99 ± 0.03。电子转移反应被表征为绝热反应，λDA = 1.16 eV 和 280 < HDA < 540 cm(-1) 与强电子耦合和缓慢的溶剂动力学一致。猝灭剂自由基对苯氧基自由基的还原被研究为 PSII 酪氨酰自由基与析氧复合物之间氧化还原反应的类似物。在我们受
• Vibrational study of the methyl viologen dication MV2+ and radical cation MV˙+ in several salts and as an intercalate in some layered MPS3 compounds
  作者：Olivier Poizat、Claude Sourisseau、Yves Mathey

  DOI：10.1039/f19848003257

  日期：——

  Infrared and Raman spectra (1800–200 cm–1) of methyl viologen (1,1′-dimethyl-4,4′-bipyridyl dication or MV2+)([1H8] and [2H8] derivatives) have been recorded for the chloride, iodide and palladate salts and for the intercalated compounds of formula M0.84 PS3–(MV)0.16(with M = Mn and Cd), FePS3–(MV)0.15 and Zn0.71 PS3–(MV)0.29. Complete assignments have been proposed for all these species. The methyl

  甲基紫精（1,1'-二甲基-4,4'-联吡啶基或MV 2 +）（[ 1 H 8 ]和[ 2 H 8 ]衍生物）的红外光谱和拉曼光谱（1800–200 cm –1）具有记录了氯化物，碘化物和钯的盐以及式M 0.84 PS 3 –（MV）0.16（其中M = Mn和Cd），FePS 3 –（MV）0.15和Zn 0.71 PS 3 –（MV的插入化合物）0.29。已经为所有这些物种提出了完整的任务。甲基紫精似乎以其双键形式插入并且与主体晶格弱相互作用。在ZnPS 3系统中，MV 2+吡啶基环扭曲，而在MnPS 3，CDPS href=https://www.molaid.com/MS_20014 target="_blank">PS 3和FePS 3中，阳离子环共面且平行于硫层。根据这些结果，建立了MPS 3主晶格中MV 2+堆积的模型，该模型解释了不同的插层速率。最后，还原产物，MV ˙+ ，已经研究了在氯化物盐和CDPS两者3插层化合物；在后一种情况下，自由基阳离子的行为就好像被稀释并截留在惰性基质中一样，证明了其出乎意料的稳定性。
• 一种百草枯的制备方法
  申请人：山东潍坊润丰化工股份有限公司

  公开号：CN107935918A

  公开（公告）日：2018-04-20

  本发明提供了一种百草枯的制备方法，包括：S1)在金属钯化合物存在的条件下，将式(I)所示的化合物与4‑吡啶硼酸混合反应，得到4,4′‑联吡啶；S2)将所述4,4′‑联吡啶与氯甲烷成盐后，得到百草枯；其中，X为卤素或三氟甲磺酰基。与现有技术相比，本发明以式(I)所示的化合物与4‑吡啶硼酸为原料，以金属钯化合物为催化剂，进行交叉偶联反应得到4,4′‑联吡啶，再与氯甲烷成盐后得到百草枯，该方法反应转化率高，反应时间短，反应条件温和，无需高温高压，对设备要求低，且无需对溶剂进行无水处理，同时该方法后处理简单，得到的产品分离，简化了生产工艺，适合大生产。