7,7',8,8'-tetracyanoquinodimethane dianion | 48161-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7,7',8,8'-tetracyanoquinodimethane dianion
• 英文别名: [2-[4-(2-Azanidylidene-1-cyanoethenyl)phenyl]-2-cyanoethenylidene]azanide；[2-[4-(2-azanidylidene-1-cyanoethenyl)phenyl]-2-cyanoethenylidene]azanide
• CAS: 48161-40-6
• 化学式: C₁₂H₄N₄
• 分子量: 204.191
• InChiKey: NRMAGWWJUWHEAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7,7,8,8-tetracyanoquinodimethane radical anion 在 四乙二醇二甲醚 、 lithium perchlorate 作用下， 生成 7,7',8,8'-tetracyanoquinodimethane dianion
  参考文献：
  名称：

  Electrochemical studies of heterogeneous reduction of tetracyanoquinodimethane in poly(ethylene oxide) electrolytes using ac impedance and cyclic voltammetry at an ultramicroelectrode

  摘要：

  使用交流阻抗光谱法和循环伏安法在铂超微电极（UME）上对 TCNQ0/TCNQ- 对偶进行了电化学研究。液体聚（环氧乙烷）（PEO）CH3-O-(CH2-CH2-O)4-CH3 被用作不同浓度 TCNQ0/TCNQ- 对偶的溶剂，LiClO4 被用作支撑电解质。根据 UME 的交流阻抗结果发现，双层电容和标准异质速率常数与电活性物质的存在和支持电解质的浓度无关，这表明电极上的电活性物质吸附并不明显。标准异质速率常数 ks 为 0.109 ± 0.005 cm s-1。第二个还原步骤 TCNQ-/TCNQ2- 也得到了类似的 ks = 0.094 cm s-1。在 0.5 M LiClO4 溶液中，TCNQ 和 TCNQ- 的扩散系数相等，D = 1.0 × 10-6 cm2 s-1。在浓度较低的支持电解质中，扩散系数较高。这些结果与之前报告的 PEO-400 HO-(CH3CH2O)8-OH 的结果进行了比较。不同的端基极大地影响了粘度，从而影响了 ks。

  DOI：

  10.1039/b004235h

文献信息

• Effect of Comproportionation on Voltammograms for Two-Electron Reactions with an Irreversible Second Electron Transfer
  作者：Mark W. Lehmann、Dennis H. Evans

  DOI：10.1021/ac990066g

  日期：1999.5.1

  Many organic and organometallic compounds are reduced or oxidized in two steps with the addition or removal of the second electron occurring with greater difficulty than the first. In such EE reactions, a comproportionation reaction can occur in solution near the electrode by which the final product exchanges an electron with the reactant to form two molecules of the intermediate species. Normally, this comproportionation reaction has little or no effect in voltammetry. In this paper, a substantial effect of comproportionation is predicted for the case where the second electron-transfer reaction is irreversible. In steady-state voltammetry, the normally symmetric, sigmoid-shaped second wave is predicted to rise more sharply near its base than is observed in the absence of comproportionation and, in the limit of a very fast comproportionation reaction, an “onset potential” develops at which the current at the second wave increases abruptly from the limiting current of the first plateau. Experimental examples of these effects are presented for the reduction of tetracyanoquinodimethane in acetonitrile by steady-state microelectrode voltammetry, normal-pulse voltammetry, and cyclic voltammetry.

  许多有机化合物和有机金属化合物的还原或氧化过程分为两个步骤，第二个电子的添加或移除比第一个步骤更加困难。在此类 EE 反应中，电极附近的溶液中会发生比例反应，最终产物与反应物交换一个电子，形成两个分子的中间产物。通常情况下，这种配比反应对伏安法影响很小或没有影响。本文预测在第二电子转移反应不可逆的情况下，比例反应会产生很大影响。据预测，在稳态伏安法中，通常对称的西格玛形第二波在其基点附近会比不发生比例反应时上升得更快，而且在发生极快比例反应的情况下，会出现 "起始电位"，此时第二波的电流会从第一高原的极限电流突然增加。通过稳态微电极伏安法、正态脉冲伏安法和循环伏安法对四氰醌二甲烷在乙腈中的还原反应，介绍了这些效应的实验实例。
• Electrochemical studies of heterogeneous reduction of tetracyanoquinodimethane in poly(ethylene oxide) electrolytes using ac impedance and cyclic voltammetry at an ultramicroelectrode
  作者：P. oś、G. Żabińska、A. Kisza、L. Christie、A. Mount、P. G. Bruce

  DOI：10.1039/b004235h

  日期：——

  Electrochemical studies of the TCNQ0/TCNQ− couple have been carried out using ac impedance spectroscopy and cyclic voltammetry at platinum ultramicroelectrodes (UME). Liquid poly(ethylene oxide) (PEO) CH3–O–(CH2–CH2–O)4–CH3 has been used as the solvent with different concentrations of the TCNQ0/TCNQ− couple and LiClO4 as the supporting electrolyte. On the basis of the ac impedance results at the UME it has been found that the double layer capacitance and standard heterogeneous rate constant are independent of the presence of electroactive species and supporting electrolyte concentrations, indicating that adsorption of electroactive species onto the electrode is not significant. The standard heterogeneous rate constant ks was found to be 0.109 ± 0.005 cm s−1. A similar value of ks = 0.094 cm s−1 was obtained for the second reduction step TCNQ−/TCNQ2−. Diffusion coefficients of both TCNQ and TCNQ− are equal, D = 1.0 × 10−6 cm2 s−1 for a 0.5 M LiClO4 solution. Higher diffusion coefficients are obtained in less concentrated supporting electrolyte. Comparison is made between these results and those reported previously for PEO-400 HO–(CH3CH2O)8–OH. The different end groups significantly influence the viscosity and hence ks.

  使用交流阻抗光谱法和循环伏安法在铂超微电极（UME）上对 TCNQ0/TCNQ- 对偶进行了电化学研究。液体聚（环氧乙烷）（PEO）CH3-O-(CH2-CH2-O)4-CH3 被用作不同浓度 TCNQ0/TCNQ- 对偶的溶剂，LiClO4 被用作支撑电解质。根据 UME 的交流阻抗结果发现，双层电容和标准异质速率常数与电活性物质的存在和支持电解质的浓度无关，这表明电极上的电活性物质吸附并不明显。标准异质速率常数 ks 为 0.109 ± 0.005 cm s-1。第二个还原步骤 TCNQ-/TCNQ2- 也得到了类似的 ks = 0.094 cm s-1。在 0.5 M LiClO4 溶液中，TCNQ 和 TCNQ- 的扩散系数相等，D = 1.0 × 10-6 cm2 s-1。在浓度较低的支持电解质中，扩散系数较高。这些结果与之前报告的 PEO-400 HO-(CH3CH2O)8-OH 的结果进行了比较。不同的端基极大地影响了粘度，从而影响了 ks。