3-carboxy-5-(2-pyridinio)-6-(2-pyridyl)-pyrazine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-carboxy-5-(2-pyridinio)-6-(2-pyridyl)-pyrazine-2-carboxylate
• 英文别名: 3-Carboxy-5-(2-pyridinio)-6-(2-pyridyl)pyrazine-2-carboxylate；5,6-dipyridin-2-ylpyrazine-2,3-dicarboxylic acid
• 化学式: C₁₆H₁₀N₄O₄
• 分子量: 322.28
• InChiKey: IBEHNEMWMYLQBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-二吡啶-2-基喹喔啉 在 potassium permanganate 作用下， 以 水 为溶剂， 反应 3.0h， 以60.5%的产率得到3-carboxy-5-(2-pyridinio)-6-(2-pyridyl)-pyrazine-2-carboxylate
  参考文献：
  名称：

  Hydrogen bonding in the inner-salt zwitterion and in two different charged forms of 5,6-bis(2-pyridyl)pyrazine-2,3-dicarboxylic acid

  摘要：

  5,6-Bis(2-pyridyl)pyrazine-2,3-dicarboxylic acid exists as an inner-salt zwitterion, 3-carboxy-5-(2-pyridinio)-6-(2-pyridyl)pyrazine-2-carboxylate, (Ia), C(16)H(10)N(4)O(4). The adjacent pyridine and pyridinium rings are almost coplanar due to the presence of an intramolecular hydrogen bond involving the pyridine N atom and the NH H atom of the pyridinium group. In the crystal of (Ia), symmetry-related molecules are hydrogen bonded via the carboxylic acid OH group and one of the carboxylate O atoms to form a polymer, which exhibits a channel-type structure. In the HCl, HClO(4) and HPF(6) salts, 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium chloride 2.25-hydrate, (II), C(16)H(11)N(4)O(4)(+).Cl(-).2.25H(2)O, 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium perchlorate trihydrate, (IIIa), C(16)H(11)N(4)O(4)(+).ClO(4)(-).3H(2)O, and 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium hexafluorophosphate trihydrate, (IIIb), C(16)H(11)N(4)O(4)(+).PF(6)(-).3H(2)O, both pyridine rings are protonated. In the perchlorate form, and in the isomorphous hexafluorophosphate form, the molecule possesses C(2) symmetry, with has a symmetrical intramolecular hydrogen bond involving the adjacent carboxylate and carboxylic acid substituents. In the crystals of the chloride and perchlorate (or hexafluorophosphate) salts, hydrogen-bonded polymers are formed which are three-dimensional and one-dimensional, respectively.

  DOI：

  10.1107/s0108270101010757

文献信息

• Hydrogen bonding in the inner-salt zwitterion and in two different charged forms of 5,6-bis(2-pyridyl)pyrazine-2,3-dicarboxylic acid
  作者：Montserrat Alfonso、Yi Wang、Helen Stoeckli-Evans

  DOI：10.1107/s0108270101010757

  日期：2001.10.15

  5,6-Bis(2-pyridyl)pyrazine-2,3-dicarboxylic acid exists as an inner-salt zwitterion, 3-carboxy-5-(2-pyridinio)-6-(2-pyridyl)pyrazine-2-carboxylate, (Ia), C(16)H(10)N(4)O(4). The adjacent pyridine and pyridinium rings are almost coplanar due to the presence of an intramolecular hydrogen bond involving the pyridine N atom and the NH H atom of the pyridinium group. In the crystal of (Ia), symmetry-related molecules are hydrogen bonded via the carboxylic acid OH group and one of the carboxylate O atoms to form a polymer, which exhibits a channel-type structure. In the HCl, HClO(4) and HPF(6) salts, 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium chloride 2.25-hydrate, (II), C(16)H(11)N(4)O(4)(+).Cl(-).2.25H(2)O, 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium perchlorate trihydrate, (IIIa), C(16)H(11)N(4)O(4)(+).ClO(4)(-).3H(2)O, and 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium hexafluorophosphate trihydrate, (IIIb), C(16)H(11)N(4)O(4)(+).PF(6)(-).3H(2)O, both pyridine rings are protonated. In the perchlorate form, and in the isomorphous hexafluorophosphate form, the molecule possesses C(2) symmetry, with has a symmetrical intramolecular hydrogen bond involving the adjacent carboxylate and carboxylic acid substituents. In the crystals of the chloride and perchlorate (or hexafluorophosphate) salts, hydrogen-bonded polymers are formed which are three-dimensional and one-dimensional, respectively.