1,4-bis(2-nonylbenzimidazol-1-ylmethyl)benzene | 1307710-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,4-bis(2-nonylbenzimidazol-1-ylmethyl)benzene
• 英文别名: Nbenzbix；2-nonyl-1-[[4-[(2-nonylbenzimidazol-1-yl)methyl]phenyl]methyl]benzimidazole
• CAS: 1307710-90-2
• 化学式: C₄₀H₅₄N₄
• 分子量: 590.896
• InChiKey: SAZYJTQMZCOCHH-UHFFFAOYSA-N

物化性质

• 沸点：
  758.8±53.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  44
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  十羰基二铼 、 6,11-二羟基-5,12-萘并萘二酮 、 1,4-bis(2-nonylbenzimidazol-1-ylmethyl)benzene 、 甲苯 以 甲苯 为溶剂， 以83%的产率得到[(CO)3Re(μ-6,11-dihydroxy-5,12-naphthacenedione(2-))(μ-1,4-bis(2-nonylbenzimidazol-1-ylmethylbenzene)Re(CO)3]*2toluene
  参考文献：
  名称：

  Adaptation toward Restricted Conformational Dynamics: From the Series of Neutral Molecular Rotors

  摘要：

  A semirigid ligand, 1,4-bis(2-nonylbenzimidazol-1-ylmethyl)benzene (Nbenzbix), containing a long alkyl chain substituted stator and a rotating unit was designed and synthesized. Three dinuclear metallacycles [(Re(CO)(3))(mu-L) (mu-Nbenzbix)(Re(CO)(3))] (1, H-2-L = H-2-dhnq = 6,11-dihydroxy-5,12-naphthacenedione; 2, H-2-L = H-2-dhaq = 1,4-dihydroxy-9,10-anthraquinone; and 3, H-2-L = H-2-CA = 2,5-dichloro-3,6-dihydroxy-p-benzoquinone) were synthesized from Re-2(CO)(10), Nbenzbix, and H-2-L units. Compounds 1-3 and the ligand Nbenzbix were characterized by elemental analysis, FT-TR, and H-1 NMR spectroscopy. Compound 1 was further characterized by a single-crystal X-ray diffraction analysis. The dynamic properties of 1-3 in solution were studied using variable-temperature H-1 NMR spectroscopy, and the findings indicate that the p-phenylene unit in the metallacycle rotates in solution. To prevent the stator units from undergoing conformational changes due to the syn/anti arrangement of the benzirnidazolyl units, a long-chain alkyl group was introduced at the 2-position of the benzimidazolyl unit. Molecular modeling calculations indicate that the energy barrier for the p-phenylene rotating unit in the metallacycle would be very low. Hence, these neutral metallacycles can be regarded as surface-mounted altitudinal rotors in which the bischelating unit is related to the surface, the nonylbenzimidazolyl units are related to the stators, and the p-phenylene is related to the rotating unit.

  DOI：

  10.1021/om200269z
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 2-壬基苯并咪唑 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到1,4-bis(2-nonylbenzimidazol-1-ylmethyl)benzene
  参考文献：
  名称：

  Adaptation toward Restricted Conformational Dynamics: From the Series of Neutral Molecular Rotors

  摘要：

  A semirigid ligand, 1,4-bis(2-nonylbenzimidazol-1-ylmethyl)benzene (Nbenzbix), containing a long alkyl chain substituted stator and a rotating unit was designed and synthesized. Three dinuclear metallacycles [(Re(CO)(3))(mu-L) (mu-Nbenzbix)(Re(CO)(3))] (1, H-2-L = H-2-dhnq = 6,11-dihydroxy-5,12-naphthacenedione; 2, H-2-L = H-2-dhaq = 1,4-dihydroxy-9,10-anthraquinone; and 3, H-2-L = H-2-CA = 2,5-dichloro-3,6-dihydroxy-p-benzoquinone) were synthesized from Re-2(CO)(10), Nbenzbix, and H-2-L units. Compounds 1-3 and the ligand Nbenzbix were characterized by elemental analysis, FT-TR, and H-1 NMR spectroscopy. Compound 1 was further characterized by a single-crystal X-ray diffraction analysis. The dynamic properties of 1-3 in solution were studied using variable-temperature H-1 NMR spectroscopy, and the findings indicate that the p-phenylene unit in the metallacycle rotates in solution. To prevent the stator units from undergoing conformational changes due to the syn/anti arrangement of the benzirnidazolyl units, a long-chain alkyl group was introduced at the 2-position of the benzimidazolyl unit. Molecular modeling calculations indicate that the energy barrier for the p-phenylene rotating unit in the metallacycle would be very low. Hence, these neutral metallacycles can be regarded as surface-mounted altitudinal rotors in which the bischelating unit is related to the surface, the nonylbenzimidazolyl units are related to the stators, and the p-phenylene is related to the rotating unit.

  DOI：

  10.1021/om200269z