(NO2)2-FDPN | 200001-79-2

• 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: (NO2)2-FDPN
• 英文别名: 7-(2-Fluoro-4-nitrophenyl)-7-(4-nitrophenyl)bicyclo[2.2.1]heptane
• CAS: 200001-79-2
• 化学式: C₁₉H₁₇FN₂O₄
• 分子量: 356.353
• InChiKey: YCYGRKKHVVNKRW-UHFFFAOYSA-N

物化性质

• 沸点：
  498.2±45.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (NO2)2-FDPN 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以100%的产率得到7-(4-amino-2-fluorophenyl)-7-(4-aminophenyl)norbornane
  参考文献：
  名称：

  Hindered Rotation in Diphenylmethane Derivatives. Electrostatic vs Charge-Transfer and Homoconjugative Aryl−Aryl Interactions

  摘要：

  A series of p,p'-disubstituted 7-phenyl-7-(2-fluorophenyl)norbornanes 5xy has been prepared, and the barrier (Delta G(#)) to 160 degrees libration around the 2-fluoroaryl-norbornane bond has been measured by DNMR. There is spectroscopic evidence of strong homoconjugative and charge-transfer (CT) interactions between both aryl groups of 5xy. However, the relationship between Delta G(#) and the nature of the substituents X and Y is accounted for only by electrostatic interactions between both aryl groups in the ground state as well as in the transition state of the libration. Therefore, the notion of CT and aromatic homoconjugation as strong attractive forces between aryl groups should be definitively rejected.

  DOI：

  10.1021/ja971388+
• 作为产物：
  描述：

  2-氟碘苯 在 三氟甲磺酸 、 magnesium 、 三氟乙酸 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 45.0h， 生成 (NO2)2-FDPN
  参考文献：
  名称：

  Hindered Rotation in Diphenylmethane Derivatives. Electrostatic vs Charge-Transfer and Homoconjugative Aryl−Aryl Interactions

  摘要：

  A series of p,p'-disubstituted 7-phenyl-7-(2-fluorophenyl)norbornanes 5xy has been prepared, and the barrier (Delta G(#)) to 160 degrees libration around the 2-fluoroaryl-norbornane bond has been measured by DNMR. There is spectroscopic evidence of strong homoconjugative and charge-transfer (CT) interactions between both aryl groups of 5xy. However, the relationship between Delta G(#) and the nature of the substituents X and Y is accounted for only by electrostatic interactions between both aryl groups in the ground state as well as in the transition state of the libration. Therefore, the notion of CT and aromatic homoconjugation as strong attractive forces between aryl groups should be definitively rejected.

  DOI：

  10.1021/ja971388+

文献信息

• A Joint Experimental and Computational Investigation on Homoconjugated Push-Pull Chromophores Derived from 7,7-Diphenylnorbornane
  作者：Noelia Herrero-García、María del Rosario Colorado Heras、María del Rosario Torres、Israel Fernández、José Osío Barcina

  DOI：10.1002/ejoc.201200159

  日期：2012.5

  spectroscopic properties and computational studies of novel aromatic homoconjugated compounds derived from 7,7-diphenylnorbornane (DPN). The UV/Vis spectra of these compounds show bands corresponding to the respective chromophores as well as new homoconjugation bands and charge transfer absorptions in D–DPN–A push-pull derivatives. Homoconjugation between the aromatic rings strongly depends on the

  我们在此报告了衍生自 7,7-二苯基降冰片烷 (DPN) 的新型芳香族同共轭化合物的合成、光谱特性和计算研究。这些化合物的紫外/可见光谱显示了对应于各自发色团的谱带以及 D-DPN-A 推挽衍生物中新的同共轭谱带和电荷转移吸收。芳环之间的同共轭很大程度上取决于芳基部分的取代性质。因此，通过控制取代基的电子性质和位置，可以很容易地调整通过同共轭进行的电子通信。强烈的共轭相互作用也反映在所研究化合物的反应性、NMR 光谱和 NLO 特性中。