1-(10-Cyano-anthracen-9-yl)-4-methyl-pyridinium | 142310-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(10-Cyano-anthracen-9-yl)-4-methyl-pyridinium
• 英文别名: 10-(4-methylpyridin-1-ium-1-yl)anthracene-9-carbonitrile
• CAS: 142310-90-5
• 化学式: C₂₁H₁₅N₂
• 分子量: 295.363
• InChiKey: OZKYYZFEBJYGKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基吡啶 、 9-cyanoanthracene cation radical 在 tert-butylammonium hexafluorophosphate(V) 作用下， 以 乙腈 为溶剂， 生成 1-(10-Cyano-anthracen-9-yl)-4-methyl-pyridinium
  参考文献：
  名称：

  Cation radical-nucleophile combination reactions. Reactions of nitrogen-centered nucleophiles with cation radicals derived from anthracenes

  摘要：

  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.

  DOI：

  10.1021/ja00018a037