3-[(2-carboxyphenyl)hydrazono]-1,1,1-trifluoropentane-2,4-dione | 709021-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(2-carboxyphenyl)hydrazono]-1,1,1-trifluoropentane-2,4-dione
• 英文别名: 2-[2-(1,1,1-trifluoro-2,4-dioxopentan-3-ylidene)hydrazinyl]benzoic acid
• CAS: 709021-44-3
• 化学式: C₁₂H₉F₃N₂O₄
• 分子量: 302.21
• InChiKey: QKPBQGKQDMFUMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  三氟乙酰丙酮 、 邻氨基苯甲酸 在 盐酸 、 sodium nitrite 、 sodium acetate 、 sodium hydroxide 作用下， 以 水 、 甲醇 为溶剂， 以92%的产率得到3-[(2-carboxyphenyl)hydrazono]-1,1,1-trifluoropentane-2,4-dione
  参考文献：
  名称：

  A new carboxylic chelate ligand and its supramolecular complexes formed with sodium ions and alcohol molecules

  摘要：

  The new hydrazone ligand 1, featuring a 2-carboxy group at the aromatic ring and a trifluoromethyl structural modification in the pentane-2,4-dione moiety, has been synthesised via the Japp-Klingemann route. The compound is shown to form binuclear multicomponent chelate complexes (2 and 3) composed of two sodium ions, two charge equalising carboxylates of the hydrazone molecule, two more carboxylic hydrazones and two alcohol solvent molecules, with the latter being either EtOH or n-BuOH. X-ray crystal structures of the free hydrazone ligand as well as of the complexes have been studied. They demonstrate for the free ligand a ribbon-type aggregation of carboxylic dimers, while the isomorphous complexes possess a remarkable binuclear structure with the two sodium ions in a distorted octahedral coordination geometry of six oxygen atoms coming, at the equatorial and apical sites, from the hydrazone carbonyl groups and the hydroxyl of the solvent molecules, respectively. The hydrogen bonds owing to the alcohol molecules give rise to the stack formation of the supramolecular cluster. Weak intermolecular contacts involving the fluorine atoms also contribute to the crystalline packing in the case of both the free ligand and the complexes.

  DOI：

  10.1080/10610270902980648

文献信息

• A new carboxylic chelate ligand and its supramolecular complexes formed with sodium ions and alcohol molecules
  作者：Jan Marten、Wilhelm Seichter、Edwin Weber

  DOI：10.1080/10610270902980648

  日期：2010.3.1

  The new hydrazone ligand 1, featuring a 2-carboxy group at the aromatic ring and a trifluoromethyl structural modification in the pentane-2,4-dione moiety, has been synthesised via the Japp-Klingemann route. The compound is shown to form binuclear multicomponent chelate complexes (2 and 3) composed of two sodium ions, two charge equalising carboxylates of the hydrazone molecule, two more carboxylic hydrazones and two alcohol solvent molecules, with the latter being either EtOH or n-BuOH. X-ray crystal structures of the free hydrazone ligand as well as of the complexes have been studied. They demonstrate for the free ligand a ribbon-type aggregation of carboxylic dimers, while the isomorphous complexes possess a remarkable binuclear structure with the two sodium ions in a distorted octahedral coordination geometry of six oxygen atoms coming, at the equatorial and apical sites, from the hydrazone carbonyl groups and the hydroxyl of the solvent molecules, respectively. The hydrogen bonds owing to the alcohol molecules give rise to the stack formation of the supramolecular cluster. Weak intermolecular contacts involving the fluorine atoms also contribute to the crystalline packing in the case of both the free ligand and the complexes.