2,6-bis(benzimidazol-2-yl)-4-tert-butylphenol

• 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: 2,6-bis(benzimidazol-2-yl)-4-tert-butylphenol
• 英文别名: 2,6-bis(1H-benzimidazol-2-yl)-4-tert-butylphenol
• 化学式: C₂₄H₂₂N₄O
• mdl: MFCD04211907
• 分子量: 382.465
• InChiKey: MPNAVBYDGRSIRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-叔丁基-2,6-二甲酰基苯酚 、 邻苯二胺 以 甲醇 为溶剂， 反应 2.0h， 以30%的产率得到2,6-bis(benzimidazol-2-yl)-4-tert-butylphenol
  参考文献：
  名称：

  Structural and optical properties of the p-alkylated 2,6-bis(benzimidazol)phenoles obtained from o-phenylenediamine and their sensitive behavior towards zinc(II) ions

  摘要：

  DOI：

  10.1016/j.poly.2022.116004

文献信息

• ——
  作者：Yu. A. Ustynyuk、N. E. Borisova、V. M. Nosova、M. D. Reshetova、S. S. Talismanov、S. E. Nefedov、G. A. Aleksandrov、I. L. Eremenko、I. I. Moiseev

  DOI：10.1023/a:1015564403703

  日期：——

  Condensation of 4-tert-butyl-2,6-diformylphenol with 1,2-diaminobenzene in ethanol is accompanied by partial reduction of the azomethine double bonds to form symmetrical macrocyclic Schiff's base containing the alternating >C=N and >CH-NH fragments. In solution, this compound exists as the only isomer in which two endocyclic hydrogen atoms are bound to the oxygen atoms of the phenol groups and two other endocyclic H atoms are attached to the nitrogen atoms of the CH2-NH fragments. All endocyclic protons are involved in hydrogen bonding and undergo rapid exchange with each other at room temperature. In the crystal, the planar macrocyclic molecules are arranged in closely packed stacks. The steric hindrances resulting from overlapping of the bulky tert-butyl groups are eliminated through rotation of the molecules with respect to each other in the adjacent layers. Study of the potential energy surface for the Schiff's base under consideration by the DFT method demonstrated that the structure corresponding to the global minimum is similar to that found in solution, However, the isolated molecule is nonplanar, its macrocycle adopting a ladder conformation. The local minimum on the potential energy surface whose energy is 2.6 kcal mol(-1) higher than that of the global minimum corresponds to the zwitterionic structure in which all four endocyclic hydrogen atoms are attached to the nitrogen atoms and the macrocycle adopts a tub conformation. Flattening of the ring is considered as a consequence of stacking interactions between the molecules in the crystal.
• Structural and optical properties of the p-alkylated 2,6-bis(benzimidazol)phenoles obtained from o-phenylenediamine and their sensitive behavior towards zinc(II) ions
  作者：Magdalena Barwiolek、Dominika Jankowska、Anna Kaczmarek-Kędziera、Tadeusz M. Muzioł

  DOI：10.1016/j.poly.2022.116004

  日期：2022.9