piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate | 1310373-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate
• 英文别名: pipzH2(2+)cdo(2-).H2O；4-oxopyran-2,6-dicarboxylate;piperazine-1,4-diium;hydrate
• CAS: 1310373-35-3
• 化学式: C₄H₁₀N₂*C₇H₄O₆*H₂O
• 分子量: 288.257
• InChiKey: NHGLQCUONRTWEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.33
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate 在 nickel(II) nitrate hexahydrate 作用下， 以 水 为溶剂， 反应 168.0h， 生成 piperazine-1,4-diium bis(6-carboxy-4-oxo-4H-pyran-2-carboxylate)
  参考文献：
  名称：

  Statistically disordered short hydrogen bonds in (pipzH₂)(cdoH)₂and a comparison with (pipzH₂)(cdo)·H₂O (pipz is piperazine and cdoH₂is chelidonic acid)

  摘要：

  Two related proton-transfer compounds, namely piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate, C4H12N2 2+center dot C7H2O6 2-center dot H2O or (pipzH(2))(cdo)center dot H2O, (I), and piperazine-1,4-diium bis(6-carboxy-4-oxo-4H-pyran-2-carboxylate), C4H12N2 2+center dot 2C(7)H(3)O(6) - or (pipzH(2))(cdoH)(2), (II), were obtained by the reaction of 4-oxo-4H-pyran-2,6-dicarboxylic acid (chelidonic acid, cdoH(2)) and piperazine (pipz). In (I), both carboxyl H atoms of chelidonic acid have been transferred to piperazine to form the piperazine-1,4-diium ion. The structure is a monohydrate. All potential N-H donors are involved in N-H...O hydrogen bonds. The water molecule spans two anions via the 4-oxo group of the pyranose ring and a carboxylate O atom. The hydrogen-bonding motif is essentially two-dimensional. The structure is a pseudomerohedral twin. In the asymmetric unit of (II), the anion consists of monodeprotonated chelidonic acid, while the piperazine-1,4-diium cation is located on an inversion centre. The single carboxyl H atom is disordered in two respects. Firstly, the disordered H atom is shared equally by both carboxylic acid groups. Secondly, the H atom is statistically disordered between two positions on either side of a centre of symmetry and is engaged in a very short hydrogen-bonding interaction; the relevant O...O distances are 2.4549 (11) and 2.4395 (11) A, and the O-H...O angles are 177 (6) and 177 (5)degrees, respectively. Further hydrogen bonding of the type N-H...O places the (pipzH(2))2+ cations in pockets formed by the chains of (cdoH)- anions. In contrast with (I), the (pipzH(2))2+ cations form hydrogen-bonding arrays that are perpendicular to the anions, yielding a three-dimensional hydrogen-bonding motif. The structures of both (I) and (II) also feature pi-pi stacking interactions between aromatic rings.

  DOI：

  10.1107/s0108270111008110
• 作为产物：
  描述：

  哌嗪 、 白屈菜酸 以 甲醇 为溶剂， 生成 piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate
  参考文献：
  名称：

  Statistically disordered short hydrogen bonds in (pipzH₂)(cdoH)₂and a comparison with (pipzH₂)(cdo)·H₂O (pipz is piperazine and cdoH₂is chelidonic acid)

  摘要：

  Two related proton-transfer compounds, namely piperazine-1,4-diium 4-oxo-4H-pyran-2,6-dicarboxylate monohydrate, C4H12N2 2+center dot C7H2O6 2-center dot H2O or (pipzH(2))(cdo)center dot H2O, (I), and piperazine-1,4-diium bis(6-carboxy-4-oxo-4H-pyran-2-carboxylate), C4H12N2 2+center dot 2C(7)H(3)O(6) - or (pipzH(2))(cdoH)(2), (II), were obtained by the reaction of 4-oxo-4H-pyran-2,6-dicarboxylic acid (chelidonic acid, cdoH(2)) and piperazine (pipz). In (I), both carboxyl H atoms of chelidonic acid have been transferred to piperazine to form the piperazine-1,4-diium ion. The structure is a monohydrate. All potential N-H donors are involved in N-H...O hydrogen bonds. The water molecule spans two anions via the 4-oxo group of the pyranose ring and a carboxylate O atom. The hydrogen-bonding motif is essentially two-dimensional. The structure is a pseudomerohedral twin. In the asymmetric unit of (II), the anion consists of monodeprotonated chelidonic acid, while the piperazine-1,4-diium cation is located on an inversion centre. The single carboxyl H atom is disordered in two respects. Firstly, the disordered H atom is shared equally by both carboxylic acid groups. Secondly, the H atom is statistically disordered between two positions on either side of a centre of symmetry and is engaged in a very short hydrogen-bonding interaction; the relevant O...O distances are 2.4549 (11) and 2.4395 (11) A, and the O-H...O angles are 177 (6) and 177 (5)degrees, respectively. Further hydrogen bonding of the type N-H...O places the (pipzH(2))2+ cations in pockets formed by the chains of (cdoH)- anions. In contrast with (I), the (pipzH(2))2+ cations form hydrogen-bonding arrays that are perpendicular to the anions, yielding a three-dimensional hydrogen-bonding motif. The structures of both (I) and (II) also feature pi-pi stacking interactions between aromatic rings.

  DOI：

  10.1107/s0108270111008110