tris(7H-dibenzofluorenylidenemethyl)methyl anion | 96742-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tris(7H-dibenzofluorenylidenemethyl)methyl anion
• 英文别名: tris(7H-dibenzofluorenylidenemethyl)methide
• CAS: 96742-98-2
• 化学式: C₆₇H₃₉
• 分子量: 844.047
• InChiKey: KBMXVOXFGFMNOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  67
• 可旋转键数：
  3
• 环数：
  15.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  tris(7H-dibenzofluorenylidenemethyl)methyl anion 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Isolation and properties of hydrocarbon salts

  摘要：

  DOI：

  10.1021/jo00290a034
• 作为产物：
  描述：

  1-(7H-dibenzofluoren-7-yl)-2,2-bis(7H-dibenzofluorenylidenemethyl)ethene 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 tris(7H-dibenzofluorenylidenemethyl)methyl anion
  参考文献：
  名称：

  Precise control of the formation of a covalent and an ionic bond in carbocation-carbanion combination reactions

  摘要：

  The electronic effect on the selectivity of covalent or ionic bond formation was examined for the reaction of Kuhn's anion 1- (C67H39-; tris(7H-dibenzo[c,g]fluorenylidenemethyl)methide ion) and 1-aryl-2,3-dicyclopropylcyclopropenylium ions. The carbocation stability was progressively changed by varying the substituent on the phenyl ring, while the steric effect was kept essentially unchanged. The cations having the p-chlorophenyl (2a+), phenyl (2b+), m-methylphenyl (2c+), or m,m'-dimethylphenyl (2d+) group gave a covalent product, whereas a carbocation-carbanion salt was obtained from the cations having the p-methylphenyl (2e+) or p-methoxyphenyl (2f+) group. The reduction potentials E(red) of the cations, as determined by cyclic voltammetry, showed that the formation of the covalent or ionic product is switched by a small difference in stability (less-than-or-equal-to 0.4 kcal/mol) between 2d+ and 2e+. In chloroform, the salts 1-2e+ and 1-2f+ were transformed into covalent forms 1-2e and 1-2f, which can exist only in solution. When 1-(2a-d) and 1-2e,f+ were dissolved in DMSO, equilibrium between a covalent compound and ions was established. A plot of the free energy of heterolysis DELTAG(het)-degrees for 1-(2a-f) against the E(red) of the corresponding cations 2a-f+ showed that DELTAG(het)-degrees decreases as the cation is more stabilized. The heterolysis in DMSO was shown to be enhanced by ca. 13 kcal/mol both by the steric congestion in the covalent molecules and the stabilization of the cyclopropenylium ions by solvation.

  DOI：

  10.1021/jo00073a047

文献信息

• OKAMOTO, KUNIO;KITAGAWA, TOSHIKAZU;TAKEUCHI, KENICHI;KOMATSU, KOICHI;KINO+, J. ORG. CHEM., 55,(1990) N, C. 996-1002
  作者：OKAMOTO, KUNIO、KITAGAWA, TOSHIKAZU、TAKEUCHI, KENICHI、KOMATSU, KOICHI、KINO+

  DOI：——

  日期：——