N-phenacyltrimethylammonium chloride | 60595-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-phenacyltrimethylammonium chloride
• 英文别名: trimethyl-phenacyl-ammonium; chloride；Trimethyl-phenacyl-ammonium; Chlorid；Trimethyl(phenacyl)azanium;chloride
• CAS: 60595-14-4
• 化学式: C₁₁H₁₆NO*Cl
• 分子量: 213.707
• InChiKey: NBMYHTBQWFNYQP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.42
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenacyltrimethylammonium chloride 在 水 、 silver(l) oxide 作用下， 生成 1,2,3-tribenzoylcyclopropane
  参考文献：
  名称：

  Harley; Mason, Journal of the Chemical Society, 1949, p. 518

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 N-phenacyltrimethylammonium chloride
  参考文献：
  名称：

  Algar; Hickey; Sherry, Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science, 1943, vol. 49 B, p. 109,118

  摘要：

  DOI：

文献信息

• Equilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations
  作者：Xian Man Zhang、Frederick G. Bordwell、Michael Van Der Puy、Herbert E. Fried

  DOI：10.1021/jo00063a026

  日期：1993.5

  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.
• Algar et al., Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science, 1943, vol. 49 B, p. 109,118
  作者：Algar et al.

  DOI：——

  日期：——
• Algar; Sherry, Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science, 1945, vol. 50 B, p. 343,344
  作者：Algar、Sherry

  DOI：——

  日期：——
• US4068085A
  申请人：——

  公开号：US4068085A

  公开（公告）日：1978-01-10
• Harley; Mason, Journal of the Chemical Society, 1949, p. 518
  作者：Harley、Mason

  DOI：——

  日期：——