2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione compound with pyrrolidin-2-one (1:1) | 1351962-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione compound with pyrrolidin-2-one (1:1)
• CAS: 1351962-06-5
• 化学式: C₄H₇NO*C₆H₂Cl₂O₄
• 分子量: 294.091
• InChiKey: FDUXAOVVFANONF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103.7
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-吡咯烷酮 、 氯冉酸 以 乙腈 为溶剂， 生成 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione compound with pyrrolidin-2-one (1:1)
  参考文献：
  名称：

  分子晶体中自组装氢键带的剧烈重排†

  摘要：

  2-吡咯烷酮和氯苯甲酸的2：1氢键合晶体显示出结构相变，伴随着氢键合带的剧烈重排。这种现象归因于氢键的选择性和方向性。

  DOI：

  10.1039/c8cc04376k

文献信息

• Hydrogen-bonded structures of the 1:1 and 1:2 compounds of chloranilic acid with pyrrolidin-2-one and piperidin-2-one
  作者：Kazuma Gotoh、Hiroyuki Ishida

  DOI：10.1107/s0108270111048165

  日期：2011.12.15

  In the four compounds of chloranilic acid (2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione) with pyrrolidin-2-one and piperidin-2-one, namely, chloranilic acid-pyrrolidin-2-one (1/1), C6H2Cl2O4 center dot C4H7NO, (I), chloranilic acid-pyrrolidin-2-one (1/2), C6H2Cl2O4 center dot 2C(4)H(7)NO, (II), chloranilic acid-piperidin-2-one (1/1), C6H2Cl2O4 center dot C5H9NO, (III), and chloranilic acid-piperidin-2-one (1/2), C6H2Cl2O4 center dot 2C(5)H(9)NO, (IV), the shortest interactions between the two components are O-H center dot center dot center dot O hydrogen bonds, which act as the primary intermolecular interaction in the crystal structures. In (II), (III) and (IV), the chloranilic acid molecules lie about inversion centres. For (III), this necessitates the presence of two independent acid molecules. In (I), there are two formula units in the asymmetric unit. The O center dot center dot center dot O distances are 2.4728 (11) and 2.4978 (11) angstrom in (I), 2.5845 (11) angstrom in (II), 2.6223 (11) and 2.5909 (10) angstrom in (III), and 2.4484 (10) angstrom in (IV). In the hydrogen bond of (IV), the H atom is disordered over two positions with site occupancies of 0.44 (3) and 0.56 (3). This indicates that proton transfer between the acid and base has partly taken place to form ion pairs. In (I) and (II), N-H center dot center dot center dot O hydrogen bonds, the secondary intermolecular interactions, connect the pyrrolidin-2-one molecules into a dimer, while in (III) and (IV) these hydrogen bonds link the acid and base to afford three-and two-dimensional hydrogen-bonded networks, respectively.