1,3,6,8-tetrabromo-2,4,5,7,9,10-hexadeuteriopyrene | 174809-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,3,6,8-tetrabromo-2,4,5,7,9,10-hexadeuteriopyrene
• CAS: 174809-19-9
• 化学式: C₁₆H₆Br₄
• 分子量: 523.792
• InChiKey: ZKBKRTZIYOKNRG-MZWXYZOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,3,6,8-tetrabromo-2,4,5,7,9,10-hexadeuteriopyrene 在 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到2,4,5,7,9,10-hexadeuteriopyrene
  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：

  芘-同位素 在 溴 作用下， 以 硝基苯 为溶剂， 以100%的产率得到1,3,6,8-tetrabromo-2,4,5,7,9,10-hexadeuteriopyrene
  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