1,6-bis-(α-hydroxy-benzhydryl)-pyrene | 202974-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,6-bis-(α-hydroxy-benzhydryl)-pyrene
• 英文别名: 1.6-Bis-(hydroxy-diphenyl-methyl)-pyren；1,6-Bis-(α-hydroxy-benzhydryl)-pyren；[6-[Hydroxy(diphenyl)methyl]pyren-1-yl]-diphenylmethanol
• CAS: 202974-49-0
• 化学式: C₄₂H₃₀O₂
• 分子量: 566.699
• InChiKey: CLGQLJPFEPVNDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-bis-(α-hydroxy-benzhydryl)-pyrene 在 氯氟磺酰 、 氟磺酸 作用下， 生成 1,6-bis(diphenylmethylenium)pyrene dication
  参考文献：
  名称：

  Conformational Studies of Phenyl- and (1-Pyrenyl)triarylmethylcarbenium Ions:  Semiempirical Calculations and NMR Investigations under Stable Ion Conditions

  摘要：

  Highly stable crowded carbenium ions such as (1-pyrenyl)diphenylmethylcarbenium ion (2) and 1,6-(3) and 1,8-bis(diphenylmethylenium)pyrene [dication] (4) and their dibrominated analogues (3Br and 4Br) have been studied at low and at ambient temperatures. 2 shows a conventional two-ring flip (ph,ph), whereas the disubstituted pyrene derivatives show one-ring flips (py) and two-ring flips (ph,ph) with a higher rotational barrier in agreement with AM1 calculations. A series of calculations show that the AM1 method gives the transition-state energies in best agreement with experiment. The propeller-shaped geometry of these molecules is reflected in characteristic low-frequency resonances of the phenyl rings. At low temperature, 3 and 4 exist as rotational isomers with C-2 and C-s (or C-i) symmetry. In 4, steric interaction makes the two rotamers slightly different in energy (1 kcal). For 4 or 4Br, the C-13 chemical shift differences between the C-2 and the C-s species of 4 or 4Br correlate roughly with the calculated charge differences between the C-2 and the C-s species. The charge at the C+ carbon is most extensively delocalized in 2, whereas in 3 and 4 with two C+ groups the pyrene moieties are less effective in charge delocalization.

  DOI：

  10.1021/jo9715480
• 作为产物：
  描述：

  1,6-二苯甲酰芘 、 phenylmagnesium bromide 在 苯甲醚 作用下， 生成 1,6-bis-(α-hydroxy-benzhydryl)-pyrene
  参考文献：
  名称：

  Lund; Berg, Matematisk - Fysiske Meddelelser - Kongelige Danske Videnskabernes Selskab, 1941, vol. 18, # 9, p. 15

  摘要：

  DOI：

文献信息

• Lund; Berg, Matematisk - Fysiske Meddelelser - Kongelige Danske Videnskabernes Selskab, 1941, vol. 18, # 9, p. 3,16
  作者：Lund、Berg

  DOI：——

  日期：——
• Conformational Studies of Phenyl- and (1-Pyrenyl)triarylmethylcarbenium Ions:  Semiempirical Calculations and NMR Investigations under Stable Ion Conditions
  作者：Poul Erik Hansen、Jens Spanget-Larsen、Kenneth K. Laali

  DOI：10.1021/jo9715480

  日期：1998.3.1

  Highly stable crowded carbenium ions such as (1-pyrenyl)diphenylmethylcarbenium ion (2) and 1,6-(3) and 1,8-bis(diphenylmethylenium)pyrene [dication] (4) and their dibrominated analogues (3Br and 4Br) have been studied at low and at ambient temperatures. 2 shows a conventional two-ring flip (ph,ph), whereas the disubstituted pyrene derivatives show one-ring flips (py) and two-ring flips (ph,ph) with a higher rotational barrier in agreement with AM1 calculations. A series of calculations show that the AM1 method gives the transition-state energies in best agreement with experiment. The propeller-shaped geometry of these molecules is reflected in characteristic low-frequency resonances of the phenyl rings. At low temperature, 3 and 4 exist as rotational isomers with C-2 and C-s (or C-i) symmetry. In 4, steric interaction makes the two rotamers slightly different in energy (1 kcal). For 4 or 4Br, the C-13 chemical shift differences between the C-2 and the C-s species of 4 or 4Br correlate roughly with the calculated charge differences between the C-2 and the C-s species. The charge at the C+ carbon is most extensively delocalized in 2, whereas in 3 and 4 with two C+ groups the pyrene moieties are less effective in charge delocalization.
• Lund; Berg, Matematisk - Fysiske Meddelelser - Kongelige Danske Videnskabernes Selskab, 1941, vol. 18, # 9, p. 15
  作者：Lund、Berg

  DOI：——

  日期：——