tetrakis(dimethylamino)-p-benzoquinone | 13044-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetrakis(dimethylamino)-p-benzoquinone
• 英文别名: 2,3,5,6-Tetrakis(dimethylamino)cyclohexa-2,5-diene-1,4-dione；2,3,5,6-tetrakis(dimethylamino)cyclohexa-2,5-diene-1,4-dione
• CAS: 13044-90-1
• 化学式: C₁₄H₂₄N₄O₂
• 分子量: 280.37
• InChiKey: YYRIQAPSMFJXIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetrakis(dimethylamino)-p-benzoquinone 在 three-electrode system: Au ultramicroelectrode as the working electrode 、 银 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Tetrakis(dimethylamino)-p-benzoquinone cation
  参考文献：
  名称：

  Kinetics of the Electroreduction and Electrooxidation of Tetrakis(dimethylamino)-p- benzoquinone in Polar Aprotic Solvents

  摘要：

  A high-frequency ac admittance technique capable of precisely measuring rate constants greater than 1 cm s(-1) was used to collect kinetic data for both the one-electron reduction and one-electron oxidation of tetrakis-(dimethylamino)-p-benzoquinone. This study was conducted at a gold ultramicroelectrode in seven polar aprotic solvents, with varying viscosity, in the presence of 0.1 M tetraethylammonium perchlorate. In addition, the temperature dependence of the standard rate constants was determined in three of these solvents. On the basis of an analysis of the solvent effects, it is shown that the kinetic data show a variation in the degree of reaction adiabaticity and the relative sizes of both the inner- and outer-sphere components of the Gibbs energy of activation. Solvent effects on diffusion coefficients and standard potentials were also investigated. The standard reduction potential is a linear function of the solvent acceptor number, a parameter reflecting molecular solvating properties, whereas the corresponding standard potential for oxidation is a linear function of solvent polarizability, a parameter that reflects nonspecific interactions between the reactant and the solvent. The significance of these results is discussed within the context of the current models for simple heterogeneous electron transfer reactions.

  DOI：

  10.1021/jp963704x

文献信息

• Bock, Hans; Ruppert, Klaus; Naether, Christian, Angewandte Chemie, <hi>1991</hi>, vol. 103, # 9, p. 1194 - 1197
  作者：Bock, Hans、Ruppert, Klaus、Naether, Christian、Havlas, Zdenek

  DOI：——

  日期：——
• Kinetics of the Electroreduction and Electrooxidation of Tetrakis(dimethylamino)-<i>p</i>- benzoquinone in Polar Aprotic Solvents
  作者：Manjali Hoon、W. Ronald Fawcett

  DOI：10.1021/jp963704x

  日期：1997.5.1

  A high-frequency ac admittance technique capable of precisely measuring rate constants greater than 1 cm s(-1) was used to collect kinetic data for both the one-electron reduction and one-electron oxidation of tetrakis-(dimethylamino)-p-benzoquinone. This study was conducted at a gold ultramicroelectrode in seven polar aprotic solvents, with varying viscosity, in the presence of 0.1 M tetraethylammonium perchlorate. In addition, the temperature dependence of the standard rate constants was determined in three of these solvents. On the basis of an analysis of the solvent effects, it is shown that the kinetic data show a variation in the degree of reaction adiabaticity and the relative sizes of both the inner- and outer-sphere components of the Gibbs energy of activation. Solvent effects on diffusion coefficients and standard potentials were also investigated. The standard reduction potential is a linear function of the solvent acceptor number, a parameter reflecting molecular solvating properties, whereas the corresponding standard potential for oxidation is a linear function of solvent polarizability, a parameter that reflects nonspecific interactions between the reactant and the solvent. The significance of these results is discussed within the context of the current models for simple heterogeneous electron transfer reactions.