4-(tetramethyl-pyrrol-1-yl)-aniline | 781-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(tetramethyl-pyrrol-1-yl)-aniline
• 英文别名: 4-(Tetramethyl-pyrrol-1-yl)-anilin；4-(2,3,4,5-Tetramethylpyrrol-1-yl)aniline
• CAS: 781-36-2
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: IKGWDHVZGOMXCX-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  385.1±30.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,4-二甲基-己烷-2,5-二酮 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 4-(tetramethyl-pyrrol-1-yl)-aniline
  参考文献：
  名称：

  Electrochemical Oxidation and EPR Spectroscopy of Radical Cations of N-Substituted 2,3,4,5-Tetramethylpyrroles.

  摘要：

  Electrochemical oxidation of 19 N-substituted 2,3,4,5-tetramethylpyrroles has been studied in acetonitrile and dichloromethane by means of slow cyclic voltammetry and coulometry. The first oxidation consumes one electron and occurs within the potential range 0.60-0.94 V in acetonitrile and 0.78-1.17 V in dichloromethane (vs. SCE). Twelve in situ generated primary radical cations were sufficiently stable al lowered temperature in dichloromethane for EPR measurement and showed well resolved HFS. The g-values (approximate to 2.0026) and the coupling constants of 2,5-methyls (a(H) approximate to 1.5 mT), 3,4-methyls (a(H) approximate to 0.35 mT), and of the pyrrole nitrogen (a(N) approximate to 0.42 mT) are very proximate for all 12 radical cations. It can be concluded, with support from quantum chemical calculations, that the odd electron is localised entirely on the pyrrole ring in the a(2) HOMO of the parent molecule. Despite the odd electron distribution, the stability of the radical cations depends on the particular substituent attached to the pyrrole nitrogen.

  DOI：

  10.3891/acta.chem.scand.52-0399

文献信息

• Criegee; Noll, Justus Liebigs Annalen der Chemie, 1959, vol. 627, p. 1,8
  作者：Criegee、Noll

  DOI：——

  日期：——
• CRIEGEE R.; RUSTAIYAN A., CHEM. BER. <CHBE-AM>, 1975, 108, NO 3, 749-753
  作者：CRIEGEE R.、 RUSTAIYAN A.

  DOI：——

  日期：——
• Electrochemical Oxidation and EPR Spectroscopy of Radical Cations of N-Substituted 2,3,4,5-Tetramethylpyrroles.
  作者：Robert Klusák、Pavel Kubáček、Domenico C. Cupertino、Lage Pettersson、Louisa Barré、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0399

  日期：——

  Electrochemical oxidation of 19 N-substituted 2,3,4,5-tetramethylpyrroles has been studied in acetonitrile and dichloromethane by means of slow cyclic voltammetry and coulometry. The first oxidation consumes one electron and occurs within the potential range 0.60-0.94 V in acetonitrile and 0.78-1.17 V in dichloromethane (vs. SCE). Twelve in situ generated primary radical cations were sufficiently stable al lowered temperature in dichloromethane for EPR measurement and showed well resolved HFS. The g-values (approximate to 2.0026) and the coupling constants of 2,5-methyls (a(H) approximate to 1.5 mT), 3,4-methyls (a(H) approximate to 0.35 mT), and of the pyrrole nitrogen (a(N) approximate to 0.42 mT) are very proximate for all 12 radical cations. It can be concluded, with support from quantum chemical calculations, that the odd electron is localised entirely on the pyrrole ring in the a(2) HOMO of the parent molecule. Despite the odd electron distribution, the stability of the radical cations depends on the particular substituent attached to the pyrrole nitrogen.