异丙醇质子化 | 18639-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 异丙醇质子化
• 英文名称: Isopropyl alcohol protonated
• 英文别名: propan-2-ol; protonated form；Protoniertes 2-Propanol；Propan-2-yloxidanium
• CAS: 18639-80-0
• 化学式: C₃H₉O
• 分子量: 61.1039
• InChiKey: KFZMGEQAYNKOFK-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  异丙醇质子化 在 硫酸 作用下， 生成 仲丙基阳离子
  参考文献：
  名称：

  Reactions of azolium cations. I. Kinetics and mechanism of alkylation of 5-phenyltetrazole with isopropyl alcohol in aqueous sulfuric acid media

  摘要：

  AbstractAlkylation of 5‐phenyltetrazole with isopropyl alcohol in 84–99% sulfuric acid medium occurs regioselectively at N2 position of the heterocycle to produce 2‐isopropyl‐5‐phenyltetrazole. The regioselectivity is conditioned by 1H, 4H‐5‐phenyltetrazolium cation being the alkylation substratum. The reaction mechanism is proved to be two‐stage one. Its first and rate‐limiting stage is an interaction between the azolium cation and isopropyl cation generated from protonated isopropyl alcohol. The reaction rate constant was estimated as 0.47 L mol−1s−1at 25°C. Water activity scale was used for quantitative description of equilibrium of isopropyl cation formation from the protonated alcohol, and the equilibrium constant pKR+= −5.3 was evaluated from the data of the alkylation kinetics. © 1993 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550251209
• 作为产物：
  描述：

  仲丙基阳离子 在 硫酸 作用下， 生成 异丙醇质子化
  参考文献：
  名称：

  Reactions of azolium cations. I. Kinetics and mechanism of alkylation of 5-phenyltetrazole with isopropyl alcohol in aqueous sulfuric acid media

  摘要：

  AbstractAlkylation of 5‐phenyltetrazole with isopropyl alcohol in 84–99% sulfuric acid medium occurs regioselectively at N2 position of the heterocycle to produce 2‐isopropyl‐5‐phenyltetrazole. The regioselectivity is conditioned by 1H, 4H‐5‐phenyltetrazolium cation being the alkylation substratum. The reaction mechanism is proved to be two‐stage one. Its first and rate‐limiting stage is an interaction between the azolium cation and isopropyl cation generated from protonated isopropyl alcohol. The reaction rate constant was estimated as 0.47 L mol−1s−1at 25°C. Water activity scale was used for quantitative description of equilibrium of isopropyl cation formation from the protonated alcohol, and the equilibrium constant pKR+= −5.3 was evaluated from the data of the alkylation kinetics. © 1993 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550251209

文献信息

• Emsley, John; Gold, Victor; Hibbert, Frank, Journal of the Chemical Society. Perkin transactions II, 1986, p. 1279 - 1282
  作者：Emsley, John、Gold, Victor、Hibbert, Frank、Jais, M. Jamil B.

  DOI：——

  日期：——
• Alkyl-transfer reactions between protonated alcohols and ethers: gas-phase alkylation of formaldehyde
  作者：Zeev Karpas、Michael Meot-Ner

  DOI：10.1021/j100342a032

  日期：1989.3
• Ion chemistry of cyanides and isocyanides. 2. Alkylation of hydrogen cyanide and cyanides by oxygen and sulfur compounds. Gas-phase synthesis and reactions of protonated isocyanides
  作者：Michael Meot-Ner、Zeev Karpas

  DOI：10.1021/j100401a042

  日期：1986.5
• SHAXGELDIEV, M. A.;SHAMXALOV, R. M.;GORYACHEV, V. V., DOKL. AN AZSSR, 43,(1987) N 6, 29-32
  作者：SHAXGELDIEV, M. A.、SHAMXALOV, R. M.、GORYACHEV, V. V.

  DOI：——

  日期：——
• Reactions of azolium cations. I. Kinetics and mechanism of alkylation of 5-phenyltetrazole with isopropyl alcohol in aqueous sulfuric acid media
  作者：A. O. Koren、P. N. Gaponik、V. A. Ostrovskii

  DOI：10.1002/kin.550251209

  日期：1993.12

  AbstractAlkylation of 5‐phenyltetrazole with isopropyl alcohol in 84–99% sulfuric acid medium occurs regioselectively at N2 position of the heterocycle to produce 2‐isopropyl‐5‐phenyltetrazole. The regioselectivity is conditioned by 1H, 4H‐5‐phenyltetrazolium cation being the alkylation substratum. The reaction mechanism is proved to be two‐stage one. Its first and rate‐limiting stage is an interaction between the azolium cation and isopropyl cation generated from protonated isopropyl alcohol. The reaction rate constant was estimated as 0.47 L mol−1s−1at 25°C. Water activity scale was used for quantitative description of equilibrium of isopropyl cation formation from the protonated alcohol, and the equilibrium constant pKR+= −5.3 was evaluated from the data of the alkylation kinetics. © 1993 John Wiley & Sons, Inc.