sulfoethyl viologen radical | 28055-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: sulfoethyl viologen radical
• 英文别名: 2,2'(4,4'-bipyridinium-1,1'-diyl)di(ethanesulfonate)；4,4'-bipyridinium-1,1'-bis(2-ethylsulfonate)；4,4'-bipyridinium-1,1'-bis(ethanesulfonate)；1,1'-bis(2-sulfonatoethyl)-4,4'-dipyridyl；sulfoethylviologen
• CAS: 28055-98-3
• 化学式: C₁₄H₁₆N₂O₆S₂
• 分子量: 372.423
• InChiKey: MEXXUUJPPBLQTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.98
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122.16
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  sulfoethyl viologen radical 、 对苯二酚 在 盐酸胍 作用下， 以 甲醇 、 水 为溶剂， 生成 2,2'(4,4'-bipyridinium-1,1'-diyl)di(ethanesulfonate)-hydroquinone (1/2)
  参考文献：
  名称：

  A zwitterionic viologen disulfonate–hydroquinone charge-transfer crystal: 2,2′-(4,4′-bipyridinium-1,1′-diyl)di(ethanesulfonate)–hydroquinone (1/2)

  摘要：

  The structure of the title compound, C14H16N2O6S2.2C(6)H(6)O(2), consists of 2,2'-(4,4'-bipyridinium-1,1'-diyl)di(ethanesulfonate) molecules (with crystallographically imposed twofold symmetry) that are hydrogen bonded to each other, as well as to hydroquinone molecules, in a complex three-dimensional motif. The orange color of the crystals is indicative of the donor-acceptor interaction between the electron-rich hydroquinone pi-donor and the electron-dercient bipyridinium pi-acceptor. The dihedral angle between the bipyridyl planes is 38.31 (11) degrees. The distance from the centroid of one of the hydroquinone molecules to the center of the bipyridinium group is 3.653 (3) Angstrom, which is within the range typically observed for molecular complexes exhibiting charge-transfer characteristics.

  DOI：

  10.1107/s0108270102016219
• 作为产物：
  描述：

  4,4'-联吡啶 、 sodium 2-bromethanesulfonate 以 二甲基亚砜 为溶剂， 反应 20.0h， 以17%的产率得到sulfoethyl viologen radical
  参考文献：
  名称：

  库仑对吩噻嗪和紫精之间光诱导的电子转移反应的影响

  摘要：

  DOI：

  10.1021/j100402a041

文献信息

• Viologens with charged groups: New redox carriers in reactions of photocatalytic separation of hydrogen from water in homogeneous and vesicular systems
  作者：V. E. Maier、A. N. Kitaigorodskii、N. K. Khannanov、V. Ya. Shafirovich

  DOI：10.1007/bf00957296

  日期：1987.11
• A Photochromic Zwitterionic Viologen: 4,4'-Bipyridinium-1,1'-bis(2-ethylsulfonate) Monohydrate
  作者：L. A. Vermeulen、P. D. Robinson

  DOI：10.1107/s0108270195013989

  日期：1996.4.15

  The structural analysis of the title compound, C14H16-N2O6S2.H2O, shows that the packing of the zwitterionic molecule in the crystal is such that the anionic sulfonate groups are located between the dicationic bipyridinium groups of adjacent molecules. Hydrogen bonds between a water molecule and the sulfonate groups link adjacent molecules into infinite molecular chains. The bipyridinium portions of adjacent molecules are not parallel, but form an angle of 58.0(1)degrees with respect to one another, forming a wedge within which the anionic groups are located.