perfluorophenylchlorodiazirine | 1312886-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: perfluorophenylchlorodiazirine
• 英文别名: 3-chloro-3-pentafluorophenyldiazirine；3-Chloro-3-(2,3,4,5,6-pentafluorophenyl)diazirine；3-chloro-3-(2,3,4,5,6-pentafluorophenyl)diazirine
• CAS: 1312886-29-5
• 化学式: C₇ClF₅N₂
• 分子量: 242.535
• InChiKey: IFQVSISGSOYLGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  perfluorophenylchlorodiazirine 以 正戊烷 为溶剂， 生成 F5-PhCCl
  参考文献：
  名称：

  Trimethoxybenzene Complexes of Pentafluorophenylchlorocarbene

  摘要：

  Pentafluorophenylchlorocarbene, generated by laser flash photolysis (LFP) of pentafluorophenylchlorodiazirine, formed pi-type complexes with 1,3,5-trimethoxybenzene in pentane. The carbene and carbene complexes were in equilibrium with K = 3.21 x 10(5) M-1 at 294 K From the temperature dependence of K, Delta H degrees = -10.2 kcal/mol, Delta S degrees = 9.5 eu, and Delta G degrees = -7.4 kcal/mol at 298 K The carbene complexes were characterized by UV-vis spectroscopy and computational analysis.

  DOI：

  10.1021/jp2039493
• 作为产物：
  描述：

  五氟苯腈 在 sodium hypochlorite 、 三甲基铝 、 氯化铵 、 lithium chloride 作用下， 以 水 、 二甲基亚砜 、 甲苯 、 正戊烷 为溶剂， 反应 51.0h， 生成 perfluorophenylchlorodiazirine
  参考文献：
  名称：

  Trimethoxybenzene Complexes of Pentafluorophenylchlorocarbene

  摘要：

  Pentafluorophenylchlorocarbene, generated by laser flash photolysis (LFP) of pentafluorophenylchlorodiazirine, formed pi-type complexes with 1,3,5-trimethoxybenzene in pentane. The carbene and carbene complexes were in equilibrium with K = 3.21 x 10(5) M-1 at 294 K From the temperature dependence of K, Delta H degrees = -10.2 kcal/mol, Delta S degrees = 9.5 eu, and Delta G degrees = -7.4 kcal/mol at 298 K The carbene complexes were characterized by UV-vis spectroscopy and computational analysis.

  DOI：

  10.1021/jp2039493

文献信息

• Negative activation energies for carbene additions to tetramethoxyethylene
  作者：Lei Wang、Robert A. Moss、Karsten Krogh-Jespersen

  DOI：10.1016/j.tetlet.2016.08.001

  日期：2016.9

  Activation energies were determined for the additions of three arylhalocarbenes to tetramethoxyethylene (TMeOE) and tetramethylethylene (TME) in pentane and decane. For addition of 3,5-dinitrophenylchlorocarbene to TMeOE in decane, Ea = −10.4 ± 0.7 kcal/mol, the most negative activation energy yet encountered in a carbene–alkene addition reaction. Computational studies parallel and elucidate the experimental

  确定了在戊烷和癸烷中向四甲氧基乙烯（TMeOE）和四甲基乙烯（TME）中添加三种芳基卤代卡宾的活化能。对于在癸烷中的TMeOE中添加3,5-二硝基苯基氯卡宾，E a  = -10.4±0.7 kcal / mol，这是卡宾-烯烃加成反应中遇到的最负的活化能。计算研究平行并阐明了实验结果。
• Pentafluorophenylhalocarbenes
  作者：Robert A. Moss、Yongmaio Shen、Lei Wang、Karsten Krogh-Jespersen

  DOI：10.1021/ol2019532

  日期：2011.9.2

  Pentafluorophenylchlorocarbene and pentafluorophenylfluorocarbene are highly reactive species and effective carriers of fluorine labels via addition to alkenes and insertion into C-H bonds.