19-octadecyloxy-1-nonadecyl thioacetate | 205938-17-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: 19-octadecyloxy-1-nonadecyl thioacetate
• 英文别名: S-(19-octadecoxynonadecyl) ethanethioate
• CAS: 205938-17-6
• 化学式: C₃₉H₇₈O₂S
• 分子量: 611.113
• InChiKey: AXDJXRINILHEKD-UHFFFAOYSA-N

物化性质

• 沸点：
  647.8±28.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.18
• 重原子数：
  42.0
• 可旋转键数：
  37.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  19-octadecyloxy-1-nonadecyl thioacetate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以90%的产率得到19-octadecyloxy-1-nonadecanethiol
  参考文献：
  名称：

  In situ studies of thiol self-assembly on gold from solution using atomic force microscopy

  摘要：

  The kinetics and mechanism for the solution-phase adsorption of n-alkanethiols onto gold to form self-assembled monolayers (SAMs) have been monitored in situ using atomic force microscopy (AFM). Time-dependent AFM images reveal detailed structural information about the adsorbed layer during its growth. In 2-butanol, CH3(CH2)17SH molecules initially adsorb on gold with the molecular axis of their hydrocarbon chains oriented parallel to the surface. As the surface coverage increases to near saturation, a two-dimensional phase transition occurs and produces islands composed of molecules with their hydrocarbon axis oriented ∼30° from the surface normal. Continued exposure to the thiol solution results in a greater number of these islands and the growth of these nuclei until a SAM is formed with a commensurate (∛×∛)R30° structure. The growth of the lying-down phase follows a first-order Langmuir adsorption isotherm, while the phase transition is best described by a second-order reaction. The kinetics of the self-assembly process also depends on the chain length of the alkanethiol and the cleanness of the gold surface. Longer-chained thiols, such as CH3(CH2)17O(CH2)19SH, formed complete SAMs more rapidly than did shorter-chained thiols, such as CH3(CH2)17SH. The physisorbed, lying-down phase for CH3(CH2)17O(CH2)19SH was less homogeneous and its two-dimensional phase transition was more complicated than for CH3(CH2)17SH and CH3(CH2)21SH, as the CH3(CH2)17O(CH2)19SH molecules adopt multiple conformations. Of these, the two dominant ones are an all-trans, and another where the hydrocarbon chain adopts an all-trans conformation except for a gauche bond on both sides of the ether unit. These conformers coexist on the surface during the initial adsorption and its transition to the standing-up phase, but change to the all-trans structure in the complete SAM.

  DOI：

  10.1063/1.475908
• 作为产物：
  描述：

  19-bromononadec-1-ene 在 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 45.0h， 生成 19-octadecyloxy-1-nonadecyl thioacetate
  参考文献：
  名称：

  In situ studies of thiol self-assembly on gold from solution using atomic force microscopy

  摘要：

  The kinetics and mechanism for the solution-phase adsorption of n-alkanethiols onto gold to form self-assembled monolayers (SAMs) have been monitored in situ using atomic force microscopy (AFM). Time-dependent AFM images reveal detailed structural information about the adsorbed layer during its growth. In 2-butanol, CH3(CH2)17SH molecules initially adsorb on gold with the molecular axis of their hydrocarbon chains oriented parallel to the surface. As the surface coverage increases to near saturation, a two-dimensional phase transition occurs and produces islands composed of molecules with their hydrocarbon axis oriented ∼30° from the surface normal. Continued exposure to the thiol solution results in a greater number of these islands and the growth of these nuclei until a SAM is formed with a commensurate (∛×∛)R30° structure. The growth of the lying-down phase follows a first-order Langmuir adsorption isotherm, while the phase transition is best described by a second-order reaction. The kinetics of the self-assembly process also depends on the chain length of the alkanethiol and the cleanness of the gold surface. Longer-chained thiols, such as CH3(CH2)17O(CH2)19SH, formed complete SAMs more rapidly than did shorter-chained thiols, such as CH3(CH2)17SH. The physisorbed, lying-down phase for CH3(CH2)17O(CH2)19SH was less homogeneous and its two-dimensional phase transition was more complicated than for CH3(CH2)17SH and CH3(CH2)21SH, as the CH3(CH2)17O(CH2)19SH molecules adopt multiple conformations. Of these, the two dominant ones are an all-trans, and another where the hydrocarbon chain adopts an all-trans conformation except for a gauche bond on both sides of the ether unit. These conformers coexist on the surface during the initial adsorption and its transition to the standing-up phase, but change to the all-trans structure in the complete SAM.

  DOI：

  10.1063/1.475908