4-(N,N-dimethylamino)phenoxyl radical | 54737-34-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(N,N-dimethylamino)phenoxyl radical
• 英文别名: p-Dimethylaminophenoxy-Radikal
• CAS: 54737-34-7
• 化学式: C₈H₁₀NO
• 分子量: 136.173
• InChiKey: WZKVQJOIZLUFBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-羟基香豆素 、 4-(N,N-dimethylamino)phenoxyl radical 在 氢氧化钾 作用下， 以 水 为溶剂， 生成 7-Hydroxycumarin-Radikal 、 4-二甲氨基苯酚
  参考文献：
  名称：

  酚的单电子氧化还原电位。具有生物学意义的羟基和氨基酚及相关化合物

  摘要：

  DOI：

  10.1021/j100215a033
• 作为产物：
  描述：

  4-二甲氨基苯酚 在 氢氧化钾 、 vinyloxyl 作用下， 以 水 、 乙二醇 为溶剂， 生成 4-(N,N-dimethylamino)phenoxyl radical
  参考文献：
  名称：

  酚的单电子氧化还原电位。具有生物学意义的羟基和氨基酚及相关化合物

  摘要：

  DOI：

  10.1021/j100215a033

文献信息

• Free electron transfer from several phenols to radical cations of non-polar solvents
  作者：Mahalaxmi R. Ganapathi、Ralf Hermann、Sergei Naumov、Ortwin Brede

  DOI：10.1039/b005864p

  日期：——

  Electron-transfer reactions from phenols to parent radical cations of solvents were studied using pulse radiolysis. Phenols bearing electron-withdrawing, electron-donating and bulky substituents were investigated in non-polar solvents such as cyclohexane, n-dodecane, n-butyl chloride and 1,2-dichloroethane. The experiments revealed the direct, synchronous formation of phenoxyl radicals and phenol radical cations

  使用脉冲辐解研究了从酚类到溶剂的母体自由基阳离子的电子转移反应。在非极性溶剂如环己烷、正十二烷、正丁基氯和 1,2-二氯乙烷中研究了带有吸电子、给电子和大取代基的酚类。实验揭示了在所有情况下苯氧基自由基和苯酚自由基阳离子的直接、同步形成，并且相对量几乎相同。这可以通过两个相互竞争的电子转移通道来解释，这两个通道取决于母体溶剂自由基阳离子和溶质苯酚分子之间相遇的几何形状。该机制在微观层面进行了分析，将扩散视为一个缓慢的过程，将局部电子转移视为一个极其快速的事件。此外，分析了各种苯酚取代基和溶剂类型对电子转移机制和溶质苯酚自由基阳离子衰变动力学的影响。使用量子化学方法进一步证实了结果。
• Perfluorobutylperoxyl radical as an oxidant in various solvents
  作者：G. S. Nahor、P. Neta、Z. B. Alfassi

  DOI：10.1021/j100164a047

  日期：1991.5

  Perfluorobutylperoxyl radicals were produced by pulse radiolysis of aerated solutions of perfluorobutyl iodide. The rate constants for reaction of this radical with several organic reductants, chlorpromazine, trolox, hydroquinone, and several other phenols, were determined in various solvents and were found to be in the range of 10(5)-10(9) M-1 s-1. By comparison with other haloalkylperoxyl radicals, C4F9OO. was found to be a much more powerful oxidant, whose reactions took place more rapidly and were less sensitive to solvent and substituent effects. The rate constants (k) for oxidation of a series of para-substituted phenols by C4F9OO. gave a good linear correlation between log k and the electrophilic substituent constant sigma+, with a slope of rho+ = -2.3, indicating formation of a positively charged transition state. Parallel experiments with CCl3OO. were limited to the most reactive phenols and gave a higher slope, rho+ = -3.3. The rates of reaction of C4F9OO. with trolox and chlorpromazine were found to depend on solvent viscosity, but much less on solvent polarity and acid-base properties, probably because they were closer to the diffusion-controlled limit. The longer chain C10F21OO. was somewhat less reactive than C4F9OO. because of geometric factors.