Ethylidene-tri-furan-3-yl-λ⁵-phosphane | 905312-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: Ethylidene-tri-furan-3-yl-λ⁵-phosphane
• CAS: 905312-17-6
• 化学式: C₁₄H₁₃O₃P
• 分子量: 260.229
• InChiKey: FDCJEENFFIUDNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.42
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Ethylidene-tri-furan-3-yl-λ⁵-phosphane 、 苯甲醛 生成 、
  参考文献：
  名称：

  Electronic Properties of Furyl Substituents at Phosphorus and Their Influence on ³¹P NMR Chemical Shifts

  摘要：

  The electronic properties of 2-furyl and 3-furyl substituents attached to phosphanes and phosphonium salts were studied by means of IR spectroscopy and experimental and computational P-31 NMR spectroscopy. The heteroaromatic systems proved to be electron withdrawing with respect to phenyl substituents. However, phosphorus atoms with attached furyl substituents are strongly shielded in NMR. The reason for this phenomenon was studied by solid state P-31 MAS NMR experiments. The chemical shift tensor was extracted, and the orientation within the molecules was determined. The tensor component sigma(33), which is effected the most by furyl systems, is oriented perpendicular to the P-C bonds of the substituents. P-furyl bonds are shorter than P-phenyl bonds. We assume therefore a lower ground-state energy of the molecules, because of the electron withdrawing properties of the 2-furyl systems. The sigma(para) component of the P-31 NMR magnetic shielding is therefore smaller, which results in an overall increase of the magnetic shielding.

  DOI：

  10.1021/ja057085u
• 作为产物：
  描述：

  tri(3-furyl)phosphine 在 sodium hexamethyldisilazane 作用下， 生成 Ethylidene-tri-furan-3-yl-λ⁵-phosphane
  参考文献：
  名称：

  Electronic Properties of Furyl Substituents at Phosphorus and Their Influence on ³¹P NMR Chemical Shifts

  摘要：

  The electronic properties of 2-furyl and 3-furyl substituents attached to phosphanes and phosphonium salts were studied by means of IR spectroscopy and experimental and computational P-31 NMR spectroscopy. The heteroaromatic systems proved to be electron withdrawing with respect to phenyl substituents. However, phosphorus atoms with attached furyl substituents are strongly shielded in NMR. The reason for this phenomenon was studied by solid state P-31 MAS NMR experiments. The chemical shift tensor was extracted, and the orientation within the molecules was determined. The tensor component sigma(33), which is effected the most by furyl systems, is oriented perpendicular to the P-C bonds of the substituents. P-furyl bonds are shorter than P-phenyl bonds. We assume therefore a lower ground-state energy of the molecules, because of the electron withdrawing properties of the 2-furyl systems. The sigma(para) component of the P-31 NMR magnetic shielding is therefore smaller, which results in an overall increase of the magnetic shielding.

  DOI：

  10.1021/ja057085u