1,5-diisopropyl-3-(4'-methoxyphenyl)-6-oxoverdazyl | 1114888-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,5-diisopropyl-3-(4'-methoxyphenyl)-6-oxoverdazyl
• CAS: 1114888-97-9
• 化学式: C₁₅H₂₁N₄O₂
• 分子量: 289.357
• InChiKey: PQQSMOFSNXVCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,5-diisopropyl-6-(4-hydroxyphenyl)-6-oxoverdazyl 、 碘甲烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到1,5-diisopropyl-3-(4'-methoxyphenyl)-6-oxoverdazyl
  参考文献：
  名称：

  Structure−Property Relationships of Stable Free Radicals: Verdazyls with Electron-Rich Aryl Substituents

  摘要：

  Substitution of the 3 position of 6-oxoverdazyl free radicals with electron-rich arylamines, phenols, and aryl ethers elicits changes in the UV-vis spectra and in the pK(a) of the aryl substituents consistent with the verdazyl being electron withdrawing. The pK(a) of substituents is decreased: in 80% methanol phenols 3a and 3b have pK(a) of 10.4 and 10.9, respectively, while the ammonium ion from protonation of 3j has pK(a) = 2.4. On the basis of these measurements, Hammett parameters for the verdazyl have been estimated: sigma(-)(p) = +0.48 and sigma(m) = +0.27. The longest wavelength band in the visible spectrum is red-shifted with increasingly electron-rich aromatic rings and with increasingly polar solvents, consistent with a transition from the highest fully occupied orbital to the radical SOMO. Exceptions occur when additional interactions occur between verdazyl and substituent; hydrogen bonding in the case of 3c and steric interference for X Measurements such as ESR and electrochemistry that are dependent largely on the SOMO are relatively insensitive to changes in substituent.

  DOI：

  10.1021/jo8019829

文献信息

• Structure−Property Relationships of Stable Free Radicals: Verdazyls with Electron-Rich Aryl Substituents
  作者：Victoria Chemistruck、Dallas Chambers、David J. R. Brook

  DOI：10.1021/jo8019829

  日期：2009.3.6

  Substitution of the 3 position of 6-oxoverdazyl free radicals with electron-rich arylamines, phenols, and aryl ethers elicits changes in the UV-vis spectra and in the pK(a) of the aryl substituents consistent with the verdazyl being electron withdrawing. The pK(a) of substituents is decreased: in 80% methanol phenols 3a and 3b have pK(a) of 10.4 and 10.9, respectively, while the ammonium ion from protonation of 3j has pK(a) = 2.4. On the basis of these measurements, Hammett parameters for the verdazyl have been estimated: sigma(-)(p) = +0.48 and sigma(m) = +0.27. The longest wavelength band in the visible spectrum is red-shifted with increasingly electron-rich aromatic rings and with increasingly polar solvents, consistent with a transition from the highest fully occupied orbital to the radical SOMO. Exceptions occur when additional interactions occur between verdazyl and substituent; hydrogen bonding in the case of 3c and steric interference for X Measurements such as ESR and electrochemistry that are dependent largely on the SOMO are relatively insensitive to changes in substituent.