7H-7,11b-epidioxydibenzo[a,o]perylene | 25305-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7H-7,11b-epidioxydibenzo[a,o]perylene
• CAS: 25305-13-9
• 化学式: C₂₈H₁₆O₂
• 分子量: 384.434
• InChiKey: WYYNZPSFQSGPGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  30.0
• 可旋转键数：
  0.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7H-7,11b-epidioxydibenzo[a,o]perylene 以 甲苯 为溶剂， 生成 二苯并[a,o]苝
  参考文献：
  名称：

  Endoperoxide formation of helianthrene with triplet molecular oxygen. A spin-forbidden reaction

  摘要：

  Dibenzo[a,o]perylene (helianthrene = HEL), known to be a very reactive singlet molecular oxygen (O-1(2), 1-DELTA-g) acceptor, also reacts with molecular oxygen in its triplet ground state (O-3(2), 3-SIGMA(g)-) to form helianthrene endoperoxide (HELPO). The thermal endoperoxide formation was studied in several solvents at r m temperature. In nonpolar solvents such as toluene and carbon disulfide the temperature-dependent equilibrium, HEL + O-3(2) reversible HELPO, is established by the thermolysis of HELPO even at low temperatures. Kinetic parameters for the HELPO formation in toluene are DELTA-H double dagger = 10.2 +/- 1.0 kcal mol-1 and DELTA-S double dagger = -39 +/- 5 eu, indicating that O-1(2) is not involved in the reaction pathway. This is the first example of aromatic endoperoxide formation by reaction with molecular oxygen in its ground state.

  DOI：

  10.1021/ja00038a007
• 作为产物：
  描述：

  二苯并[a,o]苝 在 氧气 作用下， 以 甲苯 为溶剂， 生成 7H-7,11b-epidioxydibenzo[a,o]perylene
  参考文献：
  名称：

  Endoperoxide formation of helianthrene with triplet molecular oxygen. A spin-forbidden reaction

  摘要：

  Dibenzo[a,o]perylene (helianthrene = HEL), known to be a very reactive singlet molecular oxygen (O-1(2), 1-DELTA-g) acceptor, also reacts with molecular oxygen in its triplet ground state (O-3(2), 3-SIGMA(g)-) to form helianthrene endoperoxide (HELPO). The thermal endoperoxide formation was studied in several solvents at r m temperature. In nonpolar solvents such as toluene and carbon disulfide the temperature-dependent equilibrium, HEL + O-3(2) reversible HELPO, is established by the thermolysis of HELPO even at low temperatures. Kinetic parameters for the HELPO formation in toluene are DELTA-H double dagger = 10.2 +/- 1.0 kcal mol-1 and DELTA-S double dagger = -39 +/- 5 eu, indicating that O-1(2) is not involved in the reaction pathway. This is the first example of aromatic endoperoxide formation by reaction with molecular oxygen in its ground state.

  DOI：

  10.1021/ja00038a007