tetraphenylbismuth 4-hydroxybenzenesulfonate | 955409-88-8

• 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: tetraphenylbismuth 4-hydroxybenzenesulfonate
• CAS: 955409-88-8；955409-92-4
• 化学式: C₆H₅O₄S*C₂₄H₂₀Bi
• 分子量: 690.573
• InChiKey: MRHCVZIEUZHQHA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.43
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tetraphenylbismuth 4-hydroxybenzenesulfonate 、 水 以 水 为溶剂， 生成 tetraphenylbismuth 4-hydroxybenzenesulfonate monohydrate
  参考文献：
  名称：

  Synthesis and structures of organoantimony and organobismuth derivatives of 4-sulfophenol and 2,4-disulfophenol

  摘要：

  Tetraphenylbismuth 4-hydroxybenzenesulfonate (I) and tetraphenylantimony 4-hydroxybenzenesulfonate (II) are synthesized in yields up to 80% by the reaction of pentaphenylbismuth and pentaphenylantimony, respectively, with 4-sulfophenol. Compounds I and II are also prepared by the ligand redistribution reaction from pentaphenyl compounds of bismuth and antimony and triphenylbismuth bis(4-hydroxybenzenesulfonate) and triphenylantimony bis(4-hydroxybenzenesulfonate), respectively, in yields up to 87%. The recrystallization of compounds I and II from water gives crystalline hydrates Ph4BiOSO2C6H4(OH-4) center dot H2O (III) and Ph4SbOSO2C6H4(OH-4) center dot H2O (IV). Pentaphenylbismuth and pentaphenylantimony react with 2,4-disulfophenol in acetone, regardless of the ratio of the starting reactants, to form bis(tetraphenylbismuth) 4-hydroxybenzene-1,3-disulfonate (V) and bis(tetraphenyl antimony) 4-hydroxybenzene-1,3-disulfonate (VI) in yields up to 74%. According to X-ray diffraction data, coordination of the bismuth atoms in compound I is trigonal-bipyramidal with the axial oxygen atom of the 4-hydroxybenzenesulfonate group (Bi center dot center dot center dot O 2.764 angstrom). In compound II, coordination of the Sb atom is tetrahedral (CSbC angles 106.2 degrees-112.3 degrees). In crystal III, the disc lances between the central atom and the nearest oxygen atoms of the arenesulfonate group and the hydrate water molecule are 3.094 and 3.125 angstrom, respectively. Crystals V and VI consist of doubly charged anions of 2,4-disulfophenol and several distorted tetrahedral cations of letraphenylbismuthonium (CBi(1)C, CBi(2)C angles and Bi(1)-C Bi(2)-C bond lengths vary in the intervals 102.1 degrees-122.7 degrees, 105.4 degrees-114.0 degrees and 2.103-2.230, 2.187-2.209 angstrom, respectively) and tetraphenylantimonium (CSb(1)C, CSb(2)angles and Sb(1)-C, Sb(2)-C bond lengths 106.3 degrees-112.2 degrees, 101.3 degrees-122.4 degrees and 2.095-2.110, 2.092-2.123 angstrom, respectively). The Bi(1) and Sb(2) atoms are coordinated by one of the oxygen atoms of the 2,4-disulfophenol anions (distances Bi(1)center dot center dot center dot O(3) 2.803, Sb(2)center dot center dot center dot O(1) 2.704 angstrom).

  DOI：

  10.1134/s1070328407030037
• 作为产物：
  描述：

  4-羟基苯磺酸 、 pentaphenylbismuth 以 苯 为溶剂， 以90%的产率得到tetraphenylbismuth 4-hydroxybenzenesulfonate
  参考文献：
  名称：

  Synthesis and structures of organoantimony and organobismuth derivatives of 4-sulfophenol and 2,4-disulfophenol

  摘要：

  Tetraphenylbismuth 4-hydroxybenzenesulfonate (I) and tetraphenylantimony 4-hydroxybenzenesulfonate (II) are synthesized in yields up to 80% by the reaction of pentaphenylbismuth and pentaphenylantimony, respectively, with 4-sulfophenol. Compounds I and II are also prepared by the ligand redistribution reaction from pentaphenyl compounds of bismuth and antimony and triphenylbismuth bis(4-hydroxybenzenesulfonate) and triphenylantimony bis(4-hydroxybenzenesulfonate), respectively, in yields up to 87%. The recrystallization of compounds I and II from water gives crystalline hydrates Ph4BiOSO2C6H4(OH-4) center dot H2O (III) and Ph4SbOSO2C6H4(OH-4) center dot H2O (IV). Pentaphenylbismuth and pentaphenylantimony react with 2,4-disulfophenol in acetone, regardless of the ratio of the starting reactants, to form bis(tetraphenylbismuth) 4-hydroxybenzene-1,3-disulfonate (V) and bis(tetraphenyl antimony) 4-hydroxybenzene-1,3-disulfonate (VI) in yields up to 74%. According to X-ray diffraction data, coordination of the bismuth atoms in compound I is trigonal-bipyramidal with the axial oxygen atom of the 4-hydroxybenzenesulfonate group (Bi center dot center dot center dot O 2.764 angstrom). In compound II, coordination of the Sb atom is tetrahedral (CSbC angles 106.2 degrees-112.3 degrees). In crystal III, the disc lances between the central atom and the nearest oxygen atoms of the arenesulfonate group and the hydrate water molecule are 3.094 and 3.125 angstrom, respectively. Crystals V and VI consist of doubly charged anions of 2,4-disulfophenol and several distorted tetrahedral cations of letraphenylbismuthonium (CBi(1)C, CBi(2)C angles and Bi(1)-C Bi(2)-C bond lengths vary in the intervals 102.1 degrees-122.7 degrees, 105.4 degrees-114.0 degrees and 2.103-2.230, 2.187-2.209 angstrom, respectively) and tetraphenylantimonium (CSb(1)C, CSb(2)angles and Sb(1)-C, Sb(2)-C bond lengths 106.3 degrees-112.2 degrees, 101.3 degrees-122.4 degrees and 2.095-2.110, 2.092-2.123 angstrom, respectively). The Bi(1) and Sb(2) atoms are coordinated by one of the oxygen atoms of the 2,4-disulfophenol anions (distances Bi(1)center dot center dot center dot O(3) 2.803, Sb(2)center dot center dot center dot O(1) 2.704 angstrom).

  DOI：

  10.1134/s1070328407030037