tris(2,4,6-trimethoxyphenyl)phosphine selenide | 5853-63-4

• 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: tris(2,4,6-trimethoxyphenyl)phosphine selenide
• 英文别名: Tris(pentafluorphenyl)phosphansulfid；Tris-(pentafluorphenyl)-phosphinsulfid；Tri-(pentafluorphenyl)-phosphinsulfid；Tris-pentafluorphenyl-phosphinsulfid；Tris-pentafluorphenyl-thiophosphor；Phosphine sulfide, tris(pentafluorophenyl)-；tris(2,3,4,5,6-pentafluorophenyl)-sulfanylidene-λ5-phosphane
• CAS: 5853-63-4
• 化学式: C₁₈F₁₅PS
• 分子量: 564.214
• InChiKey: ZKXAGCHSURXSAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  tris(2,4,6-trimethoxyphenyl)phosphine selenide 在 potassium dichromate 作用下， 以 硫酸 、 水 、 溶剂黄146 为溶剂， 生成 1-二(2,3,4,5,6-五氟苯基)磷酰-2,3,4,5,6-五氟苯
  参考文献：
  名称：

  五氟苯基磷化学—I。三（五氟苯基）膦硫化物和三（五氟苯基）二氯磷烷

  摘要：

  DOI：

  10.1016/0022-1902(66)80352-4
• 作为产物：
  描述：

  三(五氟苯基)膦 在 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 96.0h， 以60.1%的产率得到tris(2,4,6-trimethoxyphenyl)phosphine selenide
  参考文献：
  名称：

  Assessing Phosphine–Chalcogen Bond Energetics from Calculations

  摘要：

  Phosphine chalcogenides are useful reagents in chalcogen atom transfer reactions and nanocrystal syntheses. Understanding the strength and electronic structure of these bonds is key to optimizing their use, but a limited number of experimental and computational studies probe these issues. Using density functional theory (DFT), we computationally screen multiple series of trisubstituted phosphine chalcogenide molecules with a variety of phosphorus substituents and examine how these affect the strength of the phosphorus-chalcogen bond. DFT provides valuable data on these compounds including PE bond dissociation energies, P-E bond order, Lowdin charge on phosphorus and chalcogen atoms, and molecular geometries. Experimentally monitoring the P-31 and Se-77 NMR chemical shifts and published Hammett constants provides good estimates and confirmation of the relative magnitude of electronic shielding around these nuclei and confirms the predictive value of the computational results.

  DOI：

  10.1021/acs.organomet.5b00428

文献信息

• Phosphorus–fluorine chemistry. Part XXI. Pentafluorophenylfluorophosphines and pentafluorophenylfluorophosphoranes
  作者：M. Fild、R. Schmutzler

  DOI：10.1039/j19690000840

  日期：——

  The preparation of the fluorophosphines, (C6F5)nPF3–n, and of the fluorophosphoranes, (C6F5)nPF5–n, as well as of the related oxygen species, (C6F5)nP(:O)F3–n(n= 1, 2) is described. 19F and 31P N.m.r. data for the new compounds are reported and discussed.

  （C 6 F 5）n PF 3– n的氟代膦酸酯和（C 6 F 5）n PF 5– n的氟代膦酸酯的制备以及相关的氧种类（C 6 F 5）描述n P（：O）F 3- n（n = 1，2）。报告并讨论了新化合物的19 F和31 P Nmr数据。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.3, 1.10, page 123 - 137
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.3, 1.12, page 137 - 160
  作者：

  DOI：——

  日期：——
• Pentafluorophenyl-phosphorus chemistry—I. Tris(pentafluorophenyl)phosphine sulphide and tris(pentafluorophenyl)dichlorophosphorane
  作者：H.J. Emeléus、J.M. Miller

  DOI：10.1016/0022-1902(66)80352-4

  日期：1966.2
• Assessing Phosphine–Chalcogen Bond Energetics from Calculations
  作者：Samuel R. Alvarado、Ian A. Shortt、Hua-Jun Fan、Javier Vela

  DOI：10.1021/acs.organomet.5b00428

  日期：2015.8.24

  Phosphine chalcogenides are useful reagents in chalcogen atom transfer reactions and nanocrystal syntheses. Understanding the strength and electronic structure of these bonds is key to optimizing their use, but a limited number of experimental and computational studies probe these issues. Using density functional theory (DFT), we computationally screen multiple series of trisubstituted phosphine chalcogenide molecules with a variety of phosphorus substituents and examine how these affect the strength of the phosphorus-chalcogen bond. DFT provides valuable data on these compounds including PE bond dissociation energies, P-E bond order, Lowdin charge on phosphorus and chalcogen atoms, and molecular geometries. Experimentally monitoring the P-31 and Se-77 NMR chemical shifts and published Hammett constants provides good estimates and confirmation of the relative magnitude of electronic shielding around these nuclei and confirms the predictive value of the computational results.