2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-N-propyloctanamide | 75668-30-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-N-propyloctanamide
• CAS: 75668-30-3
• 化学式: C₁₁H₈F₁₅NO
• 分子量: 455.167
• InChiKey: IICRIFBPEINZKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  40.2 °C
• 沸点：
  74.5-75.1 °C(Press: 3.2 Torr)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  全氟辛酸 在 吡啶 、 草酰氯 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-N-propyloctanamide
  参考文献：
  名称：

  N-Alkyl Perfluoroalkanamides as Low Molecular-Mass Organogelators

  摘要：

  A new class of low molecular-mass organogelators (LMOGs), N-alkyl perfluoroalkanamides, F(CF2)(n)CONH(CH2)(m)H, is described. The molecules are designed to exploit the incompatibilities of their three molecular parts, and the results demonstrate that this strategy can be used to tune molecular aggregation and gel stability. The gelating properties of these LMOGs have been examined in a wide variety of organic liquids (including alkanes, alcohols, toluene, n-perfluorooctane, CCl4, and DMSO) as a function of the N-alkyl and perfluoroalkyl chain lengths by X-ray diffraction, polarizing optical microscopy, infrared spectroscopy, differential scanning calorimetry, and small-angle neutron scattering (SANS). The gels are thermally reversible and require generally very low concentrations (<2 wt %) of LMOG. Several of the gels are stable for very long periods at room temperature. The incompatibility of the fluorocarbon and hydrocarbon segments causes the LMOGs to aggregate, probably into lamellae within the fibrils that constitute the basic unit of the gel networks. The SANS studies show that the cross-sections of fibers in the gel networks of LMOGs with shorter perfluoroalkyl chains are much larger than those with longer ones. Comparisons with the gelating properties of some analogous esters (F(CF2)(n)CO2(CH2)(m)H) and diblock perfluoroalkylalkanes (F(CF2)(n)(CH2)(m)H) indicate that additional ordering within the aggregate units is enforced by the intermolecular H bonding among amide groups that is evidenced by IR spectroscopy. Analyses of these results and structure/solvent correlations are provided.

  DOI：

  10.1021/ja0362407

文献信息

• KITA MASAYOSHI; YAMADA YUTAKA; TATEMATSU RYOICHI; OZAKI SHINPEI, YUKAGAKU, YUKAGAKU, 1980, 29, NO 7, 514-516
  作者：KITA MASAYOSHI、 YAMADA YUTAKA、 TATEMATSU RYOICHI、 OZAKI SHINPEI

  DOI：——

  日期：——
• KITA, MASAYOSHI;YAMADA, YUTAKA;TATEMATSU, RYOICHI, REPTS GOVT IND. RES. INST., NAGOYA, 1982, 31, N 4, 105-110
  作者：KITA, MASAYOSHI、YAMADA, YUTAKA、TATEMATSU, RYOICHI

  DOI：——

  日期：——
• <i>N-</i>Alkyl Perfluoroalkanamides as Low Molecular-Mass Organogelators
  作者：Mathew George、Samuel L. Snyder、Pierre Terech、Charles J. Glinka、Richard G. Weiss

  DOI：10.1021/ja0362407

  日期：2003.8.1

  A new class of low molecular-mass organogelators (LMOGs), N-alkyl perfluoroalkanamides, F(CF2)(n)CONH(CH2)(m)H, is described. The molecules are designed to exploit the incompatibilities of their three molecular parts, and the results demonstrate that this strategy can be used to tune molecular aggregation and gel stability. The gelating properties of these LMOGs have been examined in a wide variety of organic liquids (including alkanes, alcohols, toluene, n-perfluorooctane, CCl4, and DMSO) as a function of the N-alkyl and perfluoroalkyl chain lengths by X-ray diffraction, polarizing optical microscopy, infrared spectroscopy, differential scanning calorimetry, and small-angle neutron scattering (SANS). The gels are thermally reversible and require generally very low concentrations (<2 wt %) of LMOG. Several of the gels are stable for very long periods at room temperature. The incompatibility of the fluorocarbon and hydrocarbon segments causes the LMOGs to aggregate, probably into lamellae within the fibrils that constitute the basic unit of the gel networks. The SANS studies show that the cross-sections of fibers in the gel networks of LMOGs with shorter perfluoroalkyl chains are much larger than those with longer ones. Comparisons with the gelating properties of some analogous esters (F(CF2)(n)CO2(CH2)(m)H) and diblock perfluoroalkylalkanes (F(CF2)(n)(CH2)(m)H) indicate that additional ordering within the aggregate units is enforced by the intermolecular H bonding among amide groups that is evidenced by IR spectroscopy. Analyses of these results and structure/solvent correlations are provided.