heptan-2-yl(propyl)sulfane | 1125575-92-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: heptan-2-yl(propyl)sulfane
• CAS: 1125575-92-9
• 化学式: C₁₀H₂₂S
• 分子量: 174.351
• InChiKey: KNKJGZJWGXFWAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  11.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-庚烯 、 丙烷-1-硫醇 在 硫酸 作用下， 以62%的产率得到heptan-2-yl(propyl)sulfane
  参考文献：
  名称：

  The electrophilic addition of thiols to olefins: A theoretical and experimental study

  摘要：

  Density functional theory with the B3LYP hybrid functional and 6-31G* basis set was used to study the geometric and electronic structure of H2C = CHR (R = H, CH3, C2H5, C3H7, C4H9, and C5H11) olefins, their carbocations formed in the addition of the proton to the olefins, R'-S-H aliphatic thiols (R' = H, CH3, C2H5, and C3H7), the products of the addition of thiols to carbocations, and the final products of the addition of thiols to olefins. The proton affinity of the olefins and the products of the addition of thiols to olefins was calculated. The conclusion was drawn that the limiting stage in the nonradical addition of thiols to olefins catalyzed by acids was proton transfer from the protonated reaction product to the olefin. The theoretical results were compared with the experimental data on the electrophilic addition of polymercaptan to heptene-1.

  DOI：

  10.1134/s0036024408120212

文献信息

• The electrophilic addition of thiols to olefins: A theoretical and experimental study
  作者：Yu. A. Borisov、A. K. Dyusengaliev、K. I. Dyusengaliev、T. P. Serikov

  DOI：10.1134/s0036024408120212

  日期：2008.12

  Density functional theory with the B3LYP hybrid functional and 6-31G* basis set was used to study the geometric and electronic structure of H2C = CHR (R = H, CH3, C2H5, C3H7, C4H9, and C5H11) olefins, their carbocations formed in the addition of the proton to the olefins, R'-S-H aliphatic thiols (R' = H, CH3, C2H5, and C3H7), the products of the addition of thiols to carbocations, and the final products of the addition of thiols to olefins. The proton affinity of the olefins and the products of the addition of thiols to olefins was calculated. The conclusion was drawn that the limiting stage in the nonradical addition of thiols to olefins catalyzed by acids was proton transfer from the protonated reaction product to the olefin. The theoretical results were compared with the experimental data on the electrophilic addition of polymercaptan to heptene-1.