1,4-bis(2-benzyl-1,2-dicarba-closo-dodecaboran-1-yl)benzene | 1257631-39-2

• 英文名称: 1,4-bis(2-benzyl-1,2-dicarba-closo-dodecaboran-1-yl)benzene
• CAS: 1257631-39-2
• 化学式: C₂₄H₃₈B₂₀
• 分子量: 542.786
• InChiKey: BOUSANYTEHHETP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  1,4-bis(1,2-dicarba-closo-dodecaboran-1-yl)benzene 、 溴甲苯 在 NaH 作用下， 以 乙二醇二甲醚 为溶剂， 以34%的产率得到1,4-bis(2-benzyl-1,2-dicarba-closo-dodecaboran-1-yl)benzene
  参考文献：
  名称：

  Conformational Control of Benzyl-o-carboranylbenzene Derivatives and Molecular Encapsulation of Acetone in the Dynamically Formed Space of 1,3,5-Tris(2-benzyl-o-carboran-1-yl)benzene

  摘要：

  A 1,3,5-substituted benzene platform has been widely used in the fields of supramolecular chemistry and molecular recognition. Here, we show that 1,3,5-tris(2-benzyl-o-carboran-1-yl)benzene 6 exhibits solvent-dependent conformation in the crystalline state. Recrystallization from dichloromethane-n-pentane gave the anti conformation 6-anti, while recrystallization from methanol-acetone gave the syn conformation 6-syn, in which the three benzyl-o-carboranyl moieties are located to one side of the central benzene ring. Interestingly, one acetone molecule is captured in the pi-rich space of 6-syn and two complexes facing each other encapsulate two acetone molecules in a pi-rich container formed by the eight benzene rings. The inclusion involves several weak interactions, that is, T-shaped C-H center dot center dot center dot pi interactions, and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. Two C-H center dot center dot center dot O interactions involving benzylic C-H hydrogens activated by the electron-withdrawing character of the o-carborane cage and the oxygen atom of the acetone seem to be the most important. DFT calculations indicate that the binding energy for entrapment of acetone is 6.6 kcal/mol. Inclusion of acetone is achieved through not only multiple C-H center dot center dot center dot O interactions but also a number of C-H center dot center dot center dot pi interactions. The third benzyl-o-carborane moiety is fixed in the syn conformation by intramolecular and intermolecular C-H center dot center dot center dot pi interactions.

  DOI：

  10.1021/ic101862n