4-dodecyl-α,α-bis(trifluoromethyl)benzyl alcohol | 2092-83-3

• 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: 4-dodecyl-α,α-bis(trifluoromethyl)benzyl alcohol
• 英文别名: 4-Dodecyl-1-<2-hydroxy-hexafluor-2-propyl>-benzol；4-(Hexafluor-2-hydroxy-2-propyl)-dodecylbenzol；2-(4-Dodecylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol；2-(4-dodecylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol
• CAS: 2092-83-3
• 化学式: C₂₁H₃₀F₆O
• 分子量: 412.459
• InChiKey: LMUOJLWBNBDQSN-UHFFFAOYSA-N

物化性质

• 沸点：
  128-130 °C(Press: 2 Torr)
• 密度：
  1.121±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-dodecyl-α,α-bis(trifluoromethyl)benzyl alcohol 、 碘甲烷 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 0.25h， 生成 4-dodecyl-α,α-bis(trifluoromethyl)benzyl methyl ether
  参考文献：
  名称：

  Gas chromatographic study of solute hydrogen bond basicity

  摘要：

  The purpose of the present work was to develop a scale of relative hydrogen bond basicity for a wide variety of solutes by means of their retention in gas chromatography. We used a powerful hydrogen bond donor (4-dodecyl-alpha,alpha-bis-(trifluoromethyl)benzyl alcohol) as an active hydrogen bond donor phase and a related ether (4-dodecyl-alpha,alpha-bis(trifluoromethyl)benzyl methyl ether) as a chemically similar but hydrogen bond inert reference stationary phase. The results are compared to a free energy based scale for the formation of 1:1 hydrogen bond complexes. In general, agreement is good, but a number of systematic discrepancies are found. FT-IR studies show that complexes with stoichiometries higher than 1:1 can be formed even for species as simple as THF in the presence of excess donor. Our results indicate that the use of hydrogen bond basicity scales based on the free energy of formation of hydrogen bond complexes to the rationalization of solvation-related phenomena must be used with discretion, at least in solvents which are very strong hydrogen bond acids.

  DOI：

  10.1021/ja00051a014
• 作为产物：
  描述：

  正十二烷基苯 、 六氟丙酮 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 以90%的产率得到4-dodecyl-α,α-bis(trifluoromethyl)benzyl alcohol
  参考文献：
  名称：

  Gas chromatographic study of solute hydrogen bond basicity

  摘要：

  The purpose of the present work was to develop a scale of relative hydrogen bond basicity for a wide variety of solutes by means of their retention in gas chromatography. We used a powerful hydrogen bond donor (4-dodecyl-alpha,alpha-bis-(trifluoromethyl)benzyl alcohol) as an active hydrogen bond donor phase and a related ether (4-dodecyl-alpha,alpha-bis(trifluoromethyl)benzyl methyl ether) as a chemically similar but hydrogen bond inert reference stationary phase. The results are compared to a free energy based scale for the formation of 1:1 hydrogen bond complexes. In general, agreement is good, but a number of systematic discrepancies are found. FT-IR studies show that complexes with stoichiometries higher than 1:1 can be formed even for species as simple as THF in the presence of excess donor. Our results indicate that the use of hydrogen bond basicity scales based on the free energy of formation of hydrogen bond complexes to the rationalization of solvation-related phenomena must be used with discretion, at least in solvents which are very strong hydrogen bond acids.

  DOI：

  10.1021/ja00051a014

文献信息

• Gas chromatographic study of solute hydrogen bond basicity
  作者：Jianjun Li、Yunke Zhang、Hsiu Ouyang、Peter W. Carr

  DOI：10.1021/ja00051a014

  日期：1992.12

  The purpose of the present work was to develop a scale of relative hydrogen bond basicity for a wide variety of solutes by means of their retention in gas chromatography. We used a powerful hydrogen bond donor (4-dodecyl-alpha,alpha-bis-(trifluoromethyl)benzyl alcohol) as an active hydrogen bond donor phase and a related ether (4-dodecyl-alpha,alpha-bis(trifluoromethyl)benzyl methyl ether) as a chemically similar but hydrogen bond inert reference stationary phase. The results are compared to a free energy based scale for the formation of 1:1 hydrogen bond complexes. In general, agreement is good, but a number of systematic discrepancies are found. FT-IR studies show that complexes with stoichiometries higher than 1:1 can be formed even for species as simple as THF in the presence of excess donor. Our results indicate that the use of hydrogen bond basicity scales based on the free energy of formation of hydrogen bond complexes to the rationalization of solvation-related phenomena must be used with discretion, at least in solvents which are very strong hydrogen bond acids.