N-Benzoyl-4-(dimethylamino)pyridinium tetraphenylborate | 143106-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Benzoyl-4-(dimethylamino)pyridinium tetraphenylborate
• 英文别名: [4-(Dimethylamino)pyridin-1-ium-1-yl]-phenylmethanone;tetraphenylboranuide
• CAS: 143106-44-9
• 化学式: C₁₄H₁₅N₂O*C₂₄H₂₀B
• 分子量: 546.52
• InChiKey: PKVYEWYAPHKXMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-benzoyloxy-4-(4'-dimethylaminostyryl)pyridinium tetraphenylborate 、 4-二甲氨基吡啶 以 乙腈 为溶剂， 生成 4-(二甲胺基丙基)吡啶 、 N-Benzoyl-4-(dimethylamino)pyridinium tetraphenylborate
  参考文献：
  名称：

  Rate and Equilibrium Constants of Benzoyl Group Transfer between Pyridine N-Oxides

  摘要：

  在乙腈中采用停流法研究了苯甲酰基从 N-苯甲酰氧基吡啶鎓盐转移到吡啶 N-氧化物和 4-二甲氨基吡啶的 19 个转移反应的动力学特征。通过动态核磁共振光谱法测量了 4-甲氧基吡啶的相同反应速率。其他 5 个相同反应的速率是通过布朗斯梯相关性估算的。平衡常数是通过紫外分光光度法（6）、红外光谱法（2）、动力学数据（K ij = k ij /k ji ）（2）以及 logK i-j = logK i-x - logK j-x 估算得出的。二阶速率常数（k ij ）的变化范围为 102-105 l mol-1 s-1，平衡常数（K ij ）的变化范围为 102-10-2；活化参数（ΔH ≠）的变化范围为 15-50 kJ mol-1，（-ΔS ≠）的变化范围为 -20-110 J mol-1 K-1。所研究的反应是按照协同 SN2 机制通过早期缔合过渡态在一个阶段内发生的。苯甲酰基的交换速率和平衡可以用简化的马库斯方程（省略二次项）很好地描述。

  DOI：

  10.1007/s11178-005-0244-5

文献信息

• Preparation and characterization of crystalline N-acylammonium salts
  作者：Joseph A. King、Garold L. Bryant

  DOI：10.1021/jo00045a025

  日期：1992.9

  The reaction of a tertiary amine with an acid chloride or chloroformate followed by anion exchange with either sodium tetraphenylborate or silver tetrafluoroborate provides stable, nonhygroscopic, crystalline acylammonium salts.
• Rate and Equilibrium Constants of Benzoyl Group Transfer between Pyridine N-Oxides
  作者：V. I. Rybachenko、G. Schroeder、K. Yu. Chotii、B. Lenska、A. N. Red’ko、V. V. Kovalenko

  DOI：10.1007/s11178-005-0244-5

  日期：2005.5

  Kinetic characteristics of 19 transfer reactions of benzoyl group from N-benzoyloxypyridinium salts to pyridine N-oxides and 4-dimethylaminopyridine were studied in acetonitrile by the stopped-flow method. The rate of an identical reaction for 4-methoxypyridine was measured by dynamic NMR spectroscopy. For 5 other identical reactions the rates were estimated from Bronsted correlations. Equilibrium constants were estimated with the use of UV spectrophotometry (6), IR spectroscopy (2), from kinetic data (K ij = k ij /k ji ) (2), and in one case as logK i−j = logK i−x − logK j−x . The second order rate constants (k ij ) varied in the range 102–105 l mol−1 s−1, the equilibrium constants (K ij ) in the range 102–10−2; the activation parameters (ΔH ≠) were within 15–50 kJ mol−1, (−ΔS ≠) −20–110 J mol−1 K−1. The reactions under study occur in a single stage following the concerted SN2 mechanism through an early associative transition state. The benzoyl groups exchange rate and equilibrium are well described by simplified Marcus equation (omitting the quadratic term).

  在乙腈中采用停流法研究了苯甲酰基从 N-苯甲酰氧基吡啶鎓盐转移到吡啶 N-氧化物和 4-二甲氨基吡啶的 19 个转移反应的动力学特征。通过动态核磁共振光谱法测量了 4-甲氧基吡啶的相同反应速率。其他 5 个相同反应的速率是通过布朗斯梯相关性估算的。平衡常数是通过紫外分光光度法（6）、红外光谱法（2）、动力学数据（K ij = k ij /k ji ）（2）以及 logK i-j = logK i-x - logK j-x 估算得出的。二阶速率常数（k ij ）的变化范围为 102-105 l mol-1 s-1，平衡常数（K ij ）的变化范围为 102-10-2；活化参数（ΔH ≠）的变化范围为 15-50 kJ mol-1，（-ΔS ≠）的变化范围为 -20-110 J mol-1 K-1。所研究的反应是按照协同 SN2 机制通过早期缔合过渡态在一个阶段内发生的。苯甲酰基的交换速率和平衡可以用简化的马库斯方程（省略二次项）很好地描述。