pyrene-d6 radical cation

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: pyrene-d6 radical cation
• 英文别名: 1,2,3,6,7,8-Hexadeuteriopyrene；1,2,3,6,7,8-hexadeuteriopyrene
• 化学式: C₁₆H₁₀
• 分子量: 208.208
• InChiKey: BBEAQIROQSPTKN-MZWXYZOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  pyrene-d6 radical cation 在 lithium aluminium tetrahydride 、 溴 、 四氯化钛 作用下， 以 四氢呋喃 、 硝基苯 为溶剂， 反应 2.0h， 生成 2,7-dideuteriopyrene
  参考文献：
  名称：

  Relative Solution Electron Affinities of Selectively Deuteriated Pyrenes:  Correlations between Voltammetric, Electron Paramagnetic Resonance, and Semiempirical PM3 Data

  摘要：

  The equilibrium isotope effects (EIE) for the one-electron transfer between pyrene and seven regioselectively deuteriated pyrene isotopic isomers in dimethylformamide with 0.1 M tetrabutylammonium hexafluorophosphate were measured electrochemically. These data correlate linearly with the free energies (Delta G(o)) obtained in tetrahydrofuran using electron paramagnetic resonance (EPR) techniques. However, the slope of the resulting line is not unity, and it indicates that the EIE in the DMF system is only two-thirds of that in the THF system. PM3 calculated Delta G(o,)s, which would correspond to the gas phase electron transfers, also correlate linearly with both sets of experimental data, but the predicted magnitudes of the EIE's are smaller than those observed experimentally by either technique. The nonunity slopes probably reflect slight differences in ion solvation and/or ion association parameters between the anion radicals of the isotopic isomers. No general relationship between the EIE and the charge on the hydrogen/deuterium substituted carbon atom was found.

  DOI：

  10.1021/jp952098n
• 作为产物：
  描述：

  4,5,9,10-四氢芘 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 pyrene-d6 radical cation
  参考文献：
  名称：

  Relative Solution Electron Affinities of Selectively Deuteriated Pyrenes:  Correlations between Voltammetric, Electron Paramagnetic Resonance, and Semiempirical PM3 Data

  摘要：

  The equilibrium isotope effects (EIE) for the one-electron transfer between pyrene and seven regioselectively deuteriated pyrene isotopic isomers in dimethylformamide with 0.1 M tetrabutylammonium hexafluorophosphate were measured electrochemically. These data correlate linearly with the free energies (Delta G(o)) obtained in tetrahydrofuran using electron paramagnetic resonance (EPR) techniques. However, the slope of the resulting line is not unity, and it indicates that the EIE in the DMF system is only two-thirds of that in the THF system. PM3 calculated Delta G(o,)s, which would correspond to the gas phase electron transfers, also correlate linearly with both sets of experimental data, but the predicted magnitudes of the EIE's are smaller than those observed experimentally by either technique. The nonunity slopes probably reflect slight differences in ion solvation and/or ion association parameters between the anion radicals of the isotopic isomers. No general relationship between the EIE and the charge on the hydrogen/deuterium substituted carbon atom was found.

  DOI：

  10.1021/jp952098n

文献信息

• ESR studies of deuteriated polycyclic aromatic radical cations
  作者：Hong Sang、Hanqing Wang

  DOI：10.1002/mrc.1260300210

  日期：1992.2

  Several deuteriated polycyclic aromatic radical cations were studied by ESR. Their hyperfine coupling constants are reported and mechanisms for their formation are proposed.

  通过 ESR 研究了几种氘代多环芳族自由基阳离子。报告了它们的超精细耦合常数并提出了它们的形成机制。
• Relative Solution Electron Affinities of Selectively Deuteriated Pyrenes:  Correlations between Voltammetric, Electron Paramagnetic Resonance, and Semiempirical PM3 Data
  作者：Ole Hammerich、Merete F. Nielsen、Han Zuilhof、Patrick P. J. Mulder、Gerrit Lodder、Richard C. Reiter、David E. Kage、Charles V. Rice、Cheryl D. Stevenson

  DOI：10.1021/jp952098n

  日期：1996.1.1

  The equilibrium isotope effects (EIE) for the one-electron transfer between pyrene and seven regioselectively deuteriated pyrene isotopic isomers in dimethylformamide with 0.1 M tetrabutylammonium hexafluorophosphate were measured electrochemically. These data correlate linearly with the free energies (Delta G(o)) obtained in tetrahydrofuran using electron paramagnetic resonance (EPR) techniques. However, the slope of the resulting line is not unity, and it indicates that the EIE in the DMF system is only two-thirds of that in the THF system. PM3 calculated Delta G(o,)s, which would correspond to the gas phase electron transfers, also correlate linearly with both sets of experimental data, but the predicted magnitudes of the EIE's are smaller than those observed experimentally by either technique. The nonunity slopes probably reflect slight differences in ion solvation and/or ion association parameters between the anion radicals of the isotopic isomers. No general relationship between the EIE and the charge on the hydrogen/deuterium substituted carbon atom was found.