(N-tert-Butyl)acetonitrilium cation | 48028-69-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (N-tert-Butyl)acetonitrilium cation
• 英文别名: N-Ethylidyne-2-methylpropan-2-aminium；N-tert-butylacetonitrilium
• CAS: 48028-69-9
• 化学式: C₆H₁₂N
• 分子量: 98.168
• InChiKey: XSMVEMICVCFCJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  氯代叔丁烷 、 乙腈 在 五氟化锑 作用下， 以 liquid sulphur dioxide 为溶剂， 生成 (N-tert-Butyl)acetonitrilium cation
  参考文献：
  名称：

  Interaction of Acetonitrile with Olefins and Alcohols in Zeolite H-ZSM-5: In situ Solid-state NMR Characterization of the Reaction Products

  摘要：

  AbstractThe reaction products and intermediates from the interaction of acetonitrile with olefins (oct‐1‐ene) or alcohols (tert‐butyl alcohol) in zeolite H‐ZSM‐5 at 296 K have been characterized with 13C and 15N solid‐state NMR. It has been shown that coadsorption of acetonitrile and olefin on H‐ZSM‐5 gives rise to the intermediate N‐alkylnitrilium cation represents a persistent species inside a zeolite under anhydrous conditions. Upon admittance of water to the pores of the zeolite, the N‐alkylnitrilium cation slowly converts into N‐alkylamide in accordance with the classic Ritter reaction. In the case of acetonitrile and alcohol, just after coadsorption both the intermediate N‐alkylnitrilium cation and the final N‐alkyl‐amide are identified simultaneously; the former slowly disappears over a few days. Thus, 1) it has been shown that the Ritter reaction can occur not only in liquid acidic media but also on a solid acid catalyst, zeolite H‐ZSM‐5; 2) N‐alkylnitrilium cations have been detected and characterized with solid‐state NMR as persistent intermediates in the Ritter reaction for the first time while the reaction proceeds.

  DOI：

  10.1002/chem.19970030109

文献信息

• Interaction of Acetonitrile with Olefins and Alcohols in Zeolite H-ZSM-5: In situ Solid-state NMR Characterization of the Reaction Products
  作者：Alexander G. Stepanov、Mikhail V. Luzgin

  DOI：10.1002/chem.19970030109

  日期：1997.1

  AbstractThe reaction products and intermediates from the interaction of acetonitrile with olefins (oct‐1‐ene) or alcohols (tert‐butyl alcohol) in zeolite H‐ZSM‐5 at 296 K have been characterized with 13C and 15N solid‐state NMR. It has been shown that coadsorption of acetonitrile and olefin on H‐ZSM‐5 gives rise to the intermediate N‐alkylnitrilium cation represents a persistent species inside a zeolite under anhydrous conditions. Upon admittance of water to the pores of the zeolite, the N‐alkylnitrilium cation slowly converts into N‐alkylamide in accordance with the classic Ritter reaction. In the case of acetonitrile and alcohol, just after coadsorption both the intermediate N‐alkylnitrilium cation and the final N‐alkyl‐amide are identified simultaneously; the former slowly disappears over a few days. Thus, 1) it has been shown that the Ritter reaction can occur not only in liquid acidic media but also on a solid acid catalyst, zeolite H‐ZSM‐5; 2) N‐alkylnitrilium cations have been detected and characterized with solid‐state NMR as persistent intermediates in the Ritter reaction for the first time while the reaction proceeds.