phenyl 2,5-dichlorobenzenesulfonate | 41480-03-9

• 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: phenyl 2,5-dichlorobenzenesulfonate
• 英文别名: 2,5-dichloro-benzenesulfonic acid phenyl ester；2,5-Dichlor-benzolsulfonsaeure-phenylester
• CAS: 41480-03-9
• 化学式: C₁₂H₈Cl₂O₃S
• 分子量: 303.166
• InChiKey: KTTIVPKHWGEYSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二氯苄磺酸氯 、 苯酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到phenyl 2,5-dichlorobenzenesulfonate
  参考文献：
  名称：

  2,5-Dichloro-1-(ROSO2)benzene [R=C6H5, C6F5, and CH2(CF2)4H]: Synthesis, molecular structure, and solubility in supercritical CO2

  摘要：

  Highly crystalline phenyl 2,5-dichlorobenzenesulfonate (PDBS, T-melt = 86-87 degrees C) and pentafluorophenyl 2,5-dichlorobenzenesulfonate (FPDBS, T-melt = 120-122 degrees C) were synthesized. Single-crystal X-ray molecular structure determinations show that both compounds have similar three-dimensional molecular structures; however, PDBS crystals are thin platelets and FPDBS crystals form hexagonal tube-like structures that are predominately hollow at one end. PDBS crystals exhibit offset pi-stacking of the phenoxy-rings that form complete two-dimensional layers each two molecules thick. Hydrogen-bonding interactions are calculated at similar to 3.2 angstrom between the C6-hydrogen and the sulfonyl-oxygen of a neighboring molecule. On the other hand, for FPDBS, pi-stacking of the dichloro-substituted ring as well as dipole-dipole interactions of the fluorinated-phenoxy rings appears to be the predominate intermolecular interactions. Neither structure exhibits any kind of side-on interaction of the phenyl rings. PDBS and FPDBS exhibit melting point depressions of 26 and 40 degrees C, respectively, in the presence of supercritical CO2. Although both sulfonates exhibit high solubility in CO2, Much lower pressures are needed to dissolve FPDBS compared to PDBS. For example, at 100 degrees C FPDBS dissolves at 4750 psia and PDBS dissolves at 11,000 psia. The solubility data reinforce the observation that fluorinating a compound can significantly lower the conditions needed to dissolve that compound in CO2. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.014

文献信息

• Wisgert; Sawtschuk, Zhurnal Obshchei Khimii, 1956, vol. 26, p. 2268,2269;engl.Ausg.S.2537,2538
  作者：Wisgert、Sawtschuk

  DOI：——

  日期：——
• 2,5-Dichloro-1-(ROSO2)benzene [R=C6H5, C6F5, and CH2(CF2)4H]: Synthesis, molecular structure, and solubility in supercritical CO2
  作者：Michael E. Wright、Casey E. Gorish、Zhihao Shen、Mark A. McHugh

  DOI：10.1016/j.jfluchem.2005.12.014

  日期：2006.3

  Highly crystalline phenyl 2,5-dichlorobenzenesulfonate (PDBS, T-melt = 86-87 degrees C) and pentafluorophenyl 2,5-dichlorobenzenesulfonate (FPDBS, T-melt = 120-122 degrees C) were synthesized. Single-crystal X-ray molecular structure determinations show that both compounds have similar three-dimensional molecular structures; however, PDBS crystals are thin platelets and FPDBS crystals form hexagonal tube-like structures that are predominately hollow at one end. PDBS crystals exhibit offset pi-stacking of the phenoxy-rings that form complete two-dimensional layers each two molecules thick. Hydrogen-bonding interactions are calculated at similar to 3.2 angstrom between the C6-hydrogen and the sulfonyl-oxygen of a neighboring molecule. On the other hand, for FPDBS, pi-stacking of the dichloro-substituted ring as well as dipole-dipole interactions of the fluorinated-phenoxy rings appears to be the predominate intermolecular interactions. Neither structure exhibits any kind of side-on interaction of the phenyl rings. PDBS and FPDBS exhibit melting point depressions of 26 and 40 degrees C, respectively, in the presence of supercritical CO2. Although both sulfonates exhibit high solubility in CO2, Much lower pressures are needed to dissolve FPDBS compared to PDBS. For example, at 100 degrees C FPDBS dissolves at 4750 psia and PDBS dissolves at 11,000 psia. The solubility data reinforce the observation that fluorinating a compound can significantly lower the conditions needed to dissolve that compound in CO2. (c) 2006 Elsevier B.V. All rights reserved.