N-<(phenylthio)methyl>trimethylammonium chloride

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-<(phenylthio)methyl>trimethylammonium chloride
• 英文别名: N,N,N-trimethylaminomethyl phenyl sulfide chloride；N-[(phenylthio)methyl]trimethylammonium chloride；Trimethyl(phenylsulfanylmethyl)azanium;chloride
• 化学式: C₁₀H₁₆NS*Cl
• 分子量: 217.763
• InChiKey: AUZGYUQGOYLNFG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<(phenylthio)methyl>trimethylammonium chloride 在 双氧水 、 溶剂黄146 作用下， 反应 18.0h， 生成 N-<(phenylsulfonyl)methyl>trimethylammonium chloride
  参考文献：
  名称：

  Equilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations

  摘要：

  Equilibrium acidities (pK(HA)s) of the cations in sixteen N-substituted trimethylammonium salts, one N-phenacylquinuclidinium salt, eight N-substituted pyridinium salts, and N-(ethoxycarbonyl)isoquinolinium bromide, together with the oxidation potentials of their conjugate bases, have been determined in dimethyl sulfoxide (DMSO) solution. The acidifying effects of the alpha-trimethylammonium groups (alpha-Me3N+) and the alpha-pyridinium groups (alpha-PyN+) on the adjacent acidic C-H bonds in these cations were found to average about 10 and 18 pK(HA) units, respectively, in DMSO. The homolytic bond dissociation energies of the acidic C-H bonds in these cations, estimated by the combination of the equilibrium acidities with the oxidation potentials of their corresponding conjugate bases (ylides), show that the alpha-trimethylammonium groups destabilize adjacent radicals by 2-6 kcal/mol, whereas alpha-pyridinium groups stabilize adjacent radicals by 3-6 kcal/mol. The effects of alpha-pyridinium groups on the stabilization energies of the radicals derived from these cations were found to be ca. 4-10 kcal/mol smaller than those of the corresponding phenyl groups, whereas their effects on the equilibrium acidities of the cations were 5.4-13.1 pK(HA) units larger. The pK(HA) value of tetramethylammonium cation (Me4N+) was estimated by extrapolation to be about 42 in DMSO.

  DOI：

  10.1021/jo00063a026
• 作为产物：
  描述：

  氯甲基苯硫醚 、 三乙胺 以 苯 为溶剂， 反应 3.0h， 以78%的产率得到N-<(phenylthio)methyl>trimethylammonium chloride
  参考文献：
  名称：

  硫化物单线态氧反应表面上中间体的取代基指示分配。α-氢过氧硫化物氧化 C-S 键断裂的新机制

  摘要：

  报道了单线态氧与 17 个带有阴离子或自由基稳定取代基的硫化物的反应。根据氢过氧锍叶立德中间体的分配，分析了取代基在氧化裂解和硫化物氧化途径中改变产物组成的能力。有证据表明氢过氧锍叶立德以双自由基和两性离子形式存在。此外，建议分解 α-氢过氧硫化物的分子间和分子内途径使氧化 C-S 键裂解产物的取代基依赖性形成合理化。

  DOI：

  10.1021/ja004188y