1,1'-(naphthalen-1,8-diyl)cobaltocene | 1280173-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1'-(naphthalen-1,8-diyl)cobaltocene
• 英文别名: cobalt(2+);1,8-di(cyclopenta-2,4-dien-1-yl)naphthalene
• CAS: 1280173-93-4
• 化学式: C₂₀H₁₄Co
• 分子量: 313.324
• InChiKey: ZFIWAVMJAIEYBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  ferrocenium hexafluorophosphate 、 1,1'-(naphthalen-1,8-diyl)cobaltocene 以 二氯甲烷 为溶剂， 以52%的产率得到1,1'-(naphthalen-1,8-diyl)cobaltocenium hexafluorophosphate
  参考文献：
  名称：

  An ansa-Cobaltocene with a Naphthalene Handle: Synthesis and Spectroscopic and Structural Characterization

  摘要：

  The ansa-cobaltocene 1, 1'-(naphthalen-1,8-diyl)cobaltocene (2) and the corresponding cation 1,1'-(naphthalen-1,8-diyl)cobaltocenium hexafluoridophosphate (2(+)) have been synthesized utilizing two different pathways. The solid-state molecular structure of the two complexes was determined by single-crystal X-ray diffraction. The redox properties were characterized by means of cyclic voltammetry. The electronic structure of the neutral, paramagnetic complex 2 has been studied by EPR, variable-temperature (VT) H-1 NMR, and UV-vis spectroscopy, as well as DFT calculations. Due to the bent structure of the ansa-cobaltocene 2, the 2-fold degeneracy of the e,8-orbitals of the archetype cobaltocene is broken, which allows recording a well-resolved EPR spectrum at 100 K. The VT H-1 NMR measurements in the temperature range -60 to +60 degrees C confirm 2 as a pure paramagnet. DFT calculations reveal an energy gap between the SOMO and LUMO of about 263 kJ/mol.

  DOI：

  10.1021/om200013t
• 作为产物：
  描述：

  [1,8-bis(cobaltocen-1'-ylium)naphthalen bis(tetrafluoridoborate)]*0.5(nitromethane) 在 NaHg 作用下， 以 四氢呋喃 为溶剂， 生成 1,1'-(naphthalen-1,8-diyl)cobaltocene
  参考文献：
  名称：

  An ansa-Cobaltocene with a Naphthalene Handle: Synthesis and Spectroscopic and Structural Characterization

  摘要：

  The ansa-cobaltocene 1, 1'-(naphthalen-1,8-diyl)cobaltocene (2) and the corresponding cation 1,1'-(naphthalen-1,8-diyl)cobaltocenium hexafluoridophosphate (2(+)) have been synthesized utilizing two different pathways. The solid-state molecular structure of the two complexes was determined by single-crystal X-ray diffraction. The redox properties were characterized by means of cyclic voltammetry. The electronic structure of the neutral, paramagnetic complex 2 has been studied by EPR, variable-temperature (VT) H-1 NMR, and UV-vis spectroscopy, as well as DFT calculations. Due to the bent structure of the ansa-cobaltocene 2, the 2-fold degeneracy of the e,8-orbitals of the archetype cobaltocene is broken, which allows recording a well-resolved EPR spectrum at 100 K. The VT H-1 NMR measurements in the temperature range -60 to +60 degrees C confirm 2 as a pure paramagnet. DFT calculations reveal an energy gap between the SOMO and LUMO of about 263 kJ/mol.

  DOI：

  10.1021/om200013t