1-(1-methyl-1-phenylethyl)pyridinium perchlorate | 93588-27-3

• 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: 1-(1-methyl-1-phenylethyl)pyridinium perchlorate
• 英文别名: 1-(2-Phenylpropan-2-yl)pyridin-1-ium;perchlorate
• CAS: 93588-27-3
• 化学式: C₁₄H₁₆N*ClO₄
• 分子量: 297.738
• InChiKey: QGZBGCNCPYABHH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1-methyl-1-phenylethyl)pyridinium perchlorate 生成 高氯酸,吡啶
  参考文献：
  名称：

  Kinetics and mechanism of nucleophilic displacements with heterocyclics as leaving groups. Part 24. Rates and mechanism for the solvolysis of N-tert-alkylpyridinium cations in a variety of solvents

  摘要：

  DOI：

  10.1021/ja00283a026
• 作为产物：
  描述：

  吡啶 、 ALFA, ALFA-二甲基苄氯 在 silver perchlorate 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以81%的产率得到1-(1-methyl-1-phenylethyl)pyridinium perchlorate
  参考文献：
  名称：

  Kinetics and mechanism of nucleophilic displacements with heterocyclics as leaving groups. Part 24. Rates and mechanism for the solvolysis of N-tert-alkylpyridinium cations in a variety of solvents

  摘要：

  DOI：

  10.1021/ja00283a026

文献信息

• Ion−Molecule Pairs in Leaving-Group-Promoted Solvolytic Elimination Reactions
  作者：Alf Thibblin、Yoshihiro Saeki

  DOI：10.1021/jo9619645

  日期：1997.2.1

  Solvolysis of 1-(1-methyl-1-phenylethyl)pyridinium cation (1-P+) in 25% vol acetonitrile in water at 60 degrees C provides the substitution product 2-hydroxy-2-phenylpropane (1-OH) and the elimination product 2-phenylpropene (3). The fraction of elimination is about half of that obtained with an acetate leaving group of similar basicity. The total rate of reaction is dependent on the basicity of the leaving group, 1-(1-methyl-1-(4-cyanophenyl)ethyl)pyridinium cation (1-P-CN+) reacts 1100 times faster than 1-P+ which corresponds to a Bronsted parameter of beta(lg) = -0.93. Also the fraction of elimination is leaving-group dependent as expressed by a Bronsted parameter of beta = 0.12 for the dehydronation of the ion-molecule pair by the leaving group. Addition of substituted pyridines has only a minor effect on the product ratio. The reactions are concluded to occur stepwise through a common carbocation intermediate of ion-molecule pair type. The overall kinetic deuterium isotope effects using the hexadeuteriated analogs were measured as k(obs)(H)/k(obs)(D6) = 1.85 +/- 0.10 (60 degrees C) with the pyridinium ion 1-P+ and as k(obs)(H)/k(obs)(D6) = 1.53 +/- 0.06 (40 degrees C) with the 4-cyanopyridinium ion 1-P-CN+. The kinetic deuterium isotope effects on the elimination step (assuming the reaction from intermediate to alcohol is insensitive to isotopic substitution) were measured as k(e)(H)/k(e)(D6) = 2.7 +/- 0.2 for 1-P+ (60 degrees C) and 3.4 +/- 0.2 for 1-P-CN+ (40 degrees C).
• KATRITZKY, A. R.;RUBIO, O.;SZAJDA, M.;NOWAK-WYDRA, B., J. CHEM. RES. SYNOP., 1984, N 7, 234-235
  作者：KATRITZKY, A. R.、RUBIO, O.、SZAJDA, M.、NOWAK-WYDRA, B.

  DOI：——

  日期：——
• Kinetics and mechanism of nucleophilic displacements with heterocyclics as leaving groups. Part 24. Rates and mechanism for the solvolysis of N-tert-alkylpyridinium cations in a variety of solvents
  作者：Alan R. Katritzky、Bogumil. Brycki

  DOI：10.1021/ja00283a026

  日期：1986.11