16-methoxyhexadecanethiol | 115422-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 16-methoxyhexadecanethiol
• 英文别名: 16-Methoxyhexadecane-1-thiol；16-methoxyhexadecane-1-thiol
• CAS: 115422-11-2
• 化学式: C₁₇H₃₆OS
• 分子量: 288.538
• InChiKey: LKYHXNVMXYFGPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  19
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  10.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Thioacetic acid S-(16-methoxy-hexadecyl) ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 16-methoxyhexadecanethiol
  参考文献：
  名称：

  Structure and Wetting Properties of .omega.-Alkoxy-n-alkanethiolate Monolayers on Gold and Silver

  摘要：

  omega-Alkoxy-n-alkanethiols (HS(CH2)(n)OR) adsorb from solution onto the surfaces of evaporated silver and gold films and form oriented self-assembled monolayers (SAMs). For many of these SAMs (R greater than or equal to propyl), the wetting properties of the SAMs by various polar and nonpolar liquids are indistinguishable from those of SAMs derived from n-alkanethiols and suggest that the presence of the ether oxygen atom is not sensed by contacting liquids. The structures of the SAMs that form from these adsorbates on silver and gold are different from, but reminiscent of, the canted structures that form upon adsorption of n-alkanethiols (CH3(CH2)(x)SH) onto these metal surfaces. The structural differences that exist between the SAMs on the two metals do not affect the wetting properties of the SAMs. The structure of the SAMs on the two metals has been determined using X-ray photoelectron spectroscopy (XPS), reflection absorption infrared spectroscopy (RAIRS), and sum-frequency generation spectroscopy (SFS). Application of these techniques indicates that the ether oxygen atom causes a local disordering and increases the population of gauche conformations. The magnitude of this disordering depends sensitively on the position of the oxygen atom along the chain. When the oxygen atom was located similar to 2 or more methylene units away from the chain end, the terminal methyl group in the SAMs exhibited the same molecular orientations as is found in SAMs that do not contain the heteroatom This observation suggests that this type of substitution constitutes a weak perturbation of chain ordering, and one which need not affect the structure of an extended chain.

  DOI：

  10.1021/j100019a054

文献信息

• Structure and Wetting Properties of .omega.-Alkoxy-n-alkanethiolate Monolayers on Gold and Silver
  作者：Paul E. Laibinis、Colin D. Bain、Ralph G. Nuzzo、George M. Whitesides

  DOI：10.1021/j100019a054

  日期：1995.5

  omega-Alkoxy-n-alkanethiols (HS(CH2)(n)OR) adsorb from solution onto the surfaces of evaporated silver and gold films and form oriented self-assembled monolayers (SAMs). For many of these SAMs (R greater than or equal to propyl), the wetting properties of the SAMs by various polar and nonpolar liquids are indistinguishable from those of SAMs derived from n-alkanethiols and suggest that the presence of the ether oxygen atom is not sensed by contacting liquids. The structures of the SAMs that form from these adsorbates on silver and gold are different from, but reminiscent of, the canted structures that form upon adsorption of n-alkanethiols (CH3(CH2)(x)SH) onto these metal surfaces. The structural differences that exist between the SAMs on the two metals do not affect the wetting properties of the SAMs. The structure of the SAMs on the two metals has been determined using X-ray photoelectron spectroscopy (XPS), reflection absorption infrared spectroscopy (RAIRS), and sum-frequency generation spectroscopy (SFS). Application of these techniques indicates that the ether oxygen atom causes a local disordering and increases the population of gauche conformations. The magnitude of this disordering depends sensitively on the position of the oxygen atom along the chain. When the oxygen atom was located similar to 2 or more methylene units away from the chain end, the terminal methyl group in the SAMs exhibited the same molecular orientations as is found in SAMs that do not contain the heteroatom This observation suggests that this type of substitution constitutes a weak perturbation of chain ordering, and one which need not affect the structure of an extended chain.