(4-二甲基铵亚基-1-环己-2,5-二烯亚基)-二甲基铵 | 34527-56-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (4-二甲基铵亚基-1-环己-2,5-二烯亚基)-二甲基铵
• 英文名称: Tetramethyl-p-phenylenediimine
• 英文别名: N,N,N',N'-tetramethyl-p-phenylenediamine radical cation；N,N,N'N'-tetramethyl-p-phenylenediamine；N,N,N',N'-tetramethyl-N,N'-cyclohexa-2,5-diene-1,4-diylidene-bis-ammonium; excited state；N,N'-Tetramethyl-p-benzochinon-diimonium；N,N,N',N'-Tetramethyl-p-phenylendiamin；N,N,N',N'-Tetramethyl-4-quinonediiminium dication；(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-dimethylazanium
• CAS: 34527-56-5
• 化学式: C₁₀H₁₆N₂
• 分子量: 164.25
• InChiKey: MHXIENKGMSXFHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2923900090

反应信息

• 作为反应物：
  描述：

  (4-二甲基铵亚基-1-环己-2,5-二烯亚基)-二甲基铵 、 N,N-dimethyl-p-phenylenediamine radical cation 以 水 为溶剂， 生成 Wursters Rot 、 N,N,N',N'-tetramethyl-para-semiquinonediimine
  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 高氯酸 、 oxo(N,N'-ethylenebis-salicylideneiminato)chromium(V) trifluoromethanesulphonate 、 sodium perchlorate 作用下， 以 水 为溶剂， 生成 (4-二甲基铵亚基-1-环己-2,5-二烯亚基)-二甲基铵
  参考文献：
  名称：

  Two-electron oxidation of N,N,N′,N′-tetramethylphenylenediamine with a chromium(v) salen complex

  摘要：

  四甲基苯二胺 (TMPD) 与 (salen)CrVO+ 的氧化最初生成双电子产物 TMPD2+，然后与过量 TMPD 反应生成自由基阳离子 TMPDË+。 TMPD/(salen)CrVO+ 和 TMPD/TMPD2+ 反应的动力学均依赖于酸，其中 TMPD 是反应性最强的形式，而双质子化的 TMPDH22+ 对 (salen)CrVO+ 或 TMPD2+ 没有表现出明显的反应性。各个反应的具体速率常数为：TMPD/(salen)CrVO+, k = (6.28 ± 0.50) × 109 M−1 s−1, TMPDH+/(salen)CrVO+, (3.89 ± 0.31) × 105，TMPD/TMPD2+，(7.61 ± 0.42) × 108，TMPDH+/TMPD2+，(3.46 ± 0.22) × 104。

  DOI：

  10.1039/b811140e

文献信息

• Mechanism and Kinetics of the Photocatalyzed Oxidation of p-Phenylenediamines by Peroxydisulfate in the Presence of Tri-2,2'-bipyridylylruthenium(II)
  作者：Ulrich Nickel、Yao-Hong Chen、Siegfried Schneider、Maria I. Silva、Hugh D. Burrows、Sebastiao J. Formosinho

  DOI：10.1021/j100062a026

  日期：1994.3

  The autocatalytic oxidation of p-phenylenediamines with peroxydisulfate can be strongly enhanced by irradiation in the presence of tri-2,2'-bipyridylylruthenium(II). Ru(bpy)3(2+) acts as photosensitizer and photocatalyst. First, Ru(bpy)33+ is formed by quenching excited Ru*(bpy)3(2+) with S2O8(2-). Then the ruthenium(III) complex oxidizes p-phenylenediamine. The resulting Ru(bpy)3(2+) can start the cycle again. The photocatalytic oxidation of N,N-diethyl-p-phenylenediamine as well as the dark reactions were studied with stopped-flow techniques. The mechanism of this complex reaction is discussed in detail.
• Grampp, Guenter; Landgraf, Stephan; Sabou, Dana, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 1, p. 178 - 180
  作者：Grampp, Guenter、Landgraf, Stephan、Sabou, Dana、Dvoranova, Dana

  DOI：——

  日期：——