9-苯基蒽阳离子自由基 | 40807-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 9-苯基蒽阳离子自由基
• 英文名称: 9-phenylanthracene cation radical
• 英文别名: 9-Phenylanthracenradikalkation
• CAS: 40807-34-9
• 化学式: C₂₀H₁₄
• 分子量: 254.331
• InChiKey: PLBIHBKFPROZBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 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：

  9-苯基蒽阳离子自由基 在 吡啶 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 乙腈 为溶剂， 生成 9-苯基蒽
  参考文献：
  名称：

  Radical Cation-Nucleophile Combination Reactions. The Effect of Structure of Nitrogen-Centered Nucleophiles on Reaction Rates.

  摘要：

  The kinetics of the reactions of 9-phenylanthracene (PAH) radical cation with a number of nitrogen-centered nucleophiles related to pyridine have been studied in acetonitrile and dichloromethane containing Bu4NPF6. Relative rate constants with pyridine as the nucleophile in the standard reaction, were compared with those expected from the configuration mixing (CM) model assuming that the reactive center of the radical cation is either cationic (i) or radical (ii). There is no apparent positive correlation between observed reaction barriers and those(i) ArH.+ + N: --> (ArHN+)-Ar-. (ii) ArH.+ + N: --> (+ArHN.)expected by either CM model treatment. Reaction (i) is considered to be 'forbidden' while reaction (ii) is 'allowed' by the CM model treatment. The initial gaps for reactions (ii) are estimated to be of the order of 30-40 kcal mol-l lower than those for reactions (i). It is concluded that the reactions take place by pathway (i), in spite of the greater energy gap, but that the two pathways would be experimentally indistinguishable since (+ArHN.) is expected to be unstable with respect to (ArHN+)-Ar-..

  DOI：

  10.3891/acta.chem.scand.51-1035

文献信息

• Rapid, low activation energy, selective, direct reactions of cation radicals with nucleophiles. An experimental test of theory
  作者：Vernon D. Parker、Mats Tilset

  DOI：10.1021/ja00242a052

  日期：1987.4

  Etude cinetique de la reaction du radical cationique du phenyl-9 anthracene avec des derives de la pyridine

  Etude cinetique de la reaction du Radical cationique du phenyl-9 anthracene avec desderived de la pyridine
• Cation radical-nucleophile combination reactions. Reactions of nitrogen-centered nucleophiles with cation radicals derived from anthracenes
  作者：Bjorn Reitstoen、Vernon D. Parker

  DOI：10.1021/ja00018a037

  日期：1991.8

  Cation radicals derived from anthracene and 9-substituted anthracenes react with pyridine and substituted pyridines to form pyridinium salts. 9-Nitro- and 9-cyano-substituted cation radicals were observed to be about 10(2) times as reactive as unsubstituted anthracene (AH) cation radicals while the 9-phenylanthracene (PAH) cation radical was found to be from 2 to 7 times less reactive than AH*+. The reactivities of the nitrogen-centered nucleophiles were observed to depend upon both electronic and steric factors. The mechanism of the reactions involves nucleophilic attack by the nitrogen lone pair at the 10-position of the cation radical. The reaction are accompanied by a change in hybridization, sp2 to sp3, at the anthracene 10-position, giving rise to inverse deuterium kinetic isotope effects ranging from 0.7 to 0.8 when the 10-position is substituted with deuterium. An electron-transfer mechanism for the substitution reactions was ruled out on the basis of energetic considerations.
• Parker, Vernon D.; Pedersen, Monica; Reitstoeen, Bjoern, Acta Chemica Scandinavica, 1993, vol. 47, # 6, p. 560 - 564
  作者：Parker, Vernon D.、Pedersen, Monica、Reitstoeen, Bjoern

  DOI：——

  日期：——
• Reitstöen, Björn; Parker, Vernon D., Journal of the American Chemical Society, 1990, vol. 112, # 12, p. 4968 - 4969
  作者：Reitstöen, Björn、Parker, Vernon D.

  DOI：——

  日期：——