protonated N,N,N',N'-tetramethyl-p-phenylenediamine | 19513-44-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: protonated N,N,N',N'-tetramethyl-p-phenylenediamine
• 英文别名: tetra-N-methyl-benzene-1,4-diamine; monoprotonated form；Wurter's Blau；[4-(Dimethylamino)phenyl]-dimethylazanium
• CAS: 19513-44-1
• 化学式: C₁₀H₁₆N₂*H
• 分子量: 165.258
• InChiKey: CJAOGUFAAWZWNI-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  7.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Wursters Rot 、 protonated N,N,N',N'-tetramethyl-p-phenylenediamine 以 水 为溶剂， 生成 N,N,N',N'-tetramethyl-para-semiquinonediimine 、 N,N-dimethyl-p-phenylenediamine radical cation
  参考文献：
  名称：

  An Investigation of Electron Transfer Reactions between Aromatic and Quinoid Systems

  摘要：

  AbstractA classical organic redox reaction is the conversion of an aromatic compound from its reduced form R to a semioxidized state S, and further to a totally oxidized (quinoid) species T. Complex redox systems are present in a reaction of quinoid and aromatic forms derived from different parent compounds. In this case, the exchange of one or two electrons in one step between T and R can be distinguished experimentally. These reactions were investigated in a stopped‐flow apparatus with optical detection. In the system N,N,N′,N′‐tetramethyl‐para‐phenylene‐diamine/N,N‐dimethyl‐para‐phenylene‐diamine the rate constants for all elementary reactions have been determined. Protonated, and unprotonated R were found to be reactive. In this system, as well as the others considered, no direct transfer of two electrons between T1 and R2 takes place. The essential steps of the mechanism have to be seen in a mixed symproportionation yielding S1 and S2, and a subsequent fast oxidation of S2 by surplus starting material T1. As a generalization, a tangent criterion has been derived to distinguish between one‐ and two‐electron steps in such mixed redox systems.

  DOI：

  10.1002/bbpc.198800110
• 作为产物：
  描述：

  N,N,N',N'-四甲基对苯二胺 在 氧气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 protonated N,N,N',N'-tetramethyl-p-phenylenediamine
  参考文献：
  名称：

  一种新型双核铜(II)配合物与1,4-双[N,N-双(3-水杨基氨基丙基)氨基甲基]苯的合成及其对N,N,N',N'-四甲基苯氧化的催化活性-1,4-二氨基二氧苯

  摘要：

  制备并表征了具有 1,4-双 [N,N-双 (3-水杨基氨基丙基) 氨基甲基] 苯的新型双核铜 (II) 配合物。与组分单核配合物的惰性相比，该配合物显示出催化活性，用于通过双氧氧化 N,N,N',N'-四甲基-1,4-二氨基苯。

  DOI：

  10.1246/cl.1981.1031

文献信息

• SYNTHESIS OF A NEW BINUCLEAR COPPER(II) COMPLEX WITH 1,4-BIS [<i>N</i>,<i>N</i>-BIS(3-SALICYLIDENEAMINOPROPYL)AMINOMETHYL]BENZENE AND ITS CATALYTIC ACTIVITY FOR THE OXIDATION OF<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-TETRA-METHYL-1,4-DIAMINOBENZENE BY DIOXYGEN
  作者：Naoyasu Oishi、Yuzo Nishida、Sigeo Kida

  DOI：10.1246/cl.1981.1031

  日期：1981.7.5

  A new binuclear copper(II) complex with 1,4-bis[N,N-bis(3-salicylideneaminopropyl)aminomethyl]benzene was prepared and characterized. This complex showed catalytic activity for the oxidation of N,N,N′,N′-tetramethyl-1,4-diaminobenzene by dioxygen in contrast to the inertness of the component mononuclear complex.

  制备并表征了具有 1,4-双 [N,N-双 (3-水杨基氨基丙基) 氨基甲基] 苯的新型双核铜 (II) 配合物。与组分单核配合物的惰性相比，该配合物显示出催化活性，用于通过双氧氧化 N,N,N',N'-四甲基-1,4-二氨基苯。
• Rate constants for reduction of substituted methylperoxyl radicals by ascorbate ions and N,N,N',N'-tetramethyl-p-phenylenediamine
  作者：P. Neta、R. E. Huie、S. Mosseri、L. V. Shastri、J. P. Mittal、P. Maruthamuthu、S. Steenken

  DOI：10.1021/j100347a045

  日期：1989.5
• MORKOVNIK, A. S.;DIVAEVA, L. N.;OXLOBYSTIN, O. YU., ZH. OBSHCH. XIMII, 59,(1989) N2, S. 2752-2766
  作者：MORKOVNIK, A. S.、DIVAEVA, L. N.、OXLOBYSTIN, O. YU.

  DOI：——

  日期：——
• An Investigation of Electron Transfer Reactions between Aromatic and Quinoid Systems
  作者：M. Goez、W. Jaenicke、U. Nickel

  DOI：10.1002/bbpc.198800110

  日期：1988.4

  AbstractA classical organic redox reaction is the conversion of an aromatic compound from its reduced form R to a semioxidized state S, and further to a totally oxidized (quinoid) species T. Complex redox systems are present in a reaction of quinoid and aromatic forms derived from different parent compounds. In this case, the exchange of one or two electrons in one step between T and R can be distinguished experimentally. These reactions were investigated in a stopped‐flow apparatus with optical detection. In the system N,N,N′,N′‐tetramethyl‐para‐phenylene‐diamine/N,N‐dimethyl‐para‐phenylene‐diamine the rate constants for all elementary reactions have been determined. Protonated, and unprotonated R were found to be reactive. In this system, as well as the others considered, no direct transfer of two electrons between T1 and R2 takes place. The essential steps of the mechanism have to be seen in a mixed symproportionation yielding S1 and S2, and a subsequent fast oxidation of S2 by surplus starting material T1. As a generalization, a tangent criterion has been derived to distinguish between one‐ and two‐electron steps in such mixed redox systems.
• Reaction of cations of tetramethylbenzidine with colloidal clays
  作者：L. Kovar、R. DellaGuardia、J. K. Thomas

  DOI：10.1021/j150660a043

  日期：1984.8