[6,6]-(1-N-triphenylgermylmethyl-triazoline)-C60 | 1144111-33-0

• 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: [6,6]-(1-N-triphenylgermylmethyl-triazoline)-C60
• CAS: 1144111-33-0
• 化学式: C₇₉H₁₇GeN₃
• 分子量: 1080.61
• InChiKey: FIDINNVGYBENLM-UXUXQZERSA-N

物化性质

• 熔点：
  >300 °C

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  83.0
• 可旋转键数：
  5.0
• 环数：
  36.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  27.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [6,6]-(1-N-triphenylgermylmethyl-triazoline)-C60 以 邻二氯苯 为溶剂， 以9%的产率得到[6,6]-(1-N-triphenylgermylmethyl-fulleroaziridine)-C60
  参考文献：
  名称：

  Syntheses and crystal structures of azafulleroid and aziridinofullerene bearing silyl or germyl benzene

  摘要：

  Addition of silyl and germylmethyl azides (1) to fullerene C-60 at 50 degrees C through [2+3] cycloaddition led to the formation of the triazoline adducts (2). Subsequently, heating 2 at 100 degrees C in the solid state, caused N-2 extrusion producing two different isomers, [5,6]-azafulleroid (3) and [6,6]-aziridinofullerene (4). The C-13 NMR spectrum of 3 had an absence of resonances in the aliphatic region for the fullerene C-60 cage, showing a fulleroid with CS symmetry. In contrast, 4 exhibited one sp(3) resonance in the aliphatic region for the fullerene C-60 cage, indicative of an aziridinofullerene with C-2V symmetry. However, MALDI-TOF mass characterization was hampered because ion peaks corresponding to the bis-adduct are detected in positive ion mode measurements, whereas the ion peaks [M-N-2] for 2a as well as [M] for 3a and 4a are observed in negative ion measurements. In an effort to obtain X-ray data, silyl and germylphenyl groups were introduced to form intermolecular complexes with fullerene C-60. The X-ray structures of 3c and 3d revealed a strong enhancement of homoconjugation in the bridged annulene moiety based on POAV analysis. The X-ray structures of 3c,d and 4c were confirmed with the detection of silyl and germylphenyl-C-60 interactions, similar to dimethoxyphenyl-C-60 interactions. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.11.049
• 作为产物：
  描述：

  triphenylgermylmethylazide 、 足球烯 以 邻二氯苯 为溶剂， 以26%的产率得到[6,6]-(1-N-triphenylgermylmethyl-triazoline)-C60
  参考文献：
  名称：

  Syntheses and crystal structures of azafulleroid and aziridinofullerene bearing silyl or germyl benzene

  摘要：

  Addition of silyl and germylmethyl azides (1) to fullerene C-60 at 50 degrees C through [2+3] cycloaddition led to the formation of the triazoline adducts (2). Subsequently, heating 2 at 100 degrees C in the solid state, caused N-2 extrusion producing two different isomers, [5,6]-azafulleroid (3) and [6,6]-aziridinofullerene (4). The C-13 NMR spectrum of 3 had an absence of resonances in the aliphatic region for the fullerene C-60 cage, showing a fulleroid with CS symmetry. In contrast, 4 exhibited one sp(3) resonance in the aliphatic region for the fullerene C-60 cage, indicative of an aziridinofullerene with C-2V symmetry. However, MALDI-TOF mass characterization was hampered because ion peaks corresponding to the bis-adduct are detected in positive ion mode measurements, whereas the ion peaks [M-N-2] for 2a as well as [M] for 3a and 4a are observed in negative ion measurements. In an effort to obtain X-ray data, silyl and germylphenyl groups were introduced to form intermolecular complexes with fullerene C-60. The X-ray structures of 3c and 3d revealed a strong enhancement of homoconjugation in the bridged annulene moiety based on POAV analysis. The X-ray structures of 3c,d and 4c were confirmed with the detection of silyl and germylphenyl-C-60 interactions, similar to dimethoxyphenyl-C-60 interactions. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.11.049