β-cyanoethyl anion | 71857-20-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: β-cyanoethyl anion
• 英文别名: 2-cyano-ethanide；propanenitrile
• CAS: 71857-20-0
• 化学式: C₃H₄N
• 分子量: 54.0715
• InChiKey: ZEQZMKBUMATFGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氰基乙基三甲基硅烷 在 氢氟酸 作用下， 生成 β-cyanoethyl anion 、 、
  参考文献：
  名称：

  β-Cyanoethyl Anion:  Lusus Naturae

  摘要：

  A stable E1(cb) intermediate, beta-cyanoethyl anion (1 beta), has been synthesized in the gas phase at room temperature under thermal conditions via the fluoride-induced desilylation of 3-(trimethylsilyl)propionitrile. The reactivity and thermodynamic properties of this ion are reported. The cyano group is found to lower the proton affinity of 1 beta by 29 +/- 6 kcal/mol, which represents a particularly large substituent effect. High-level ab initio and density functional calculations have been carried out on 1 beta and several related species. The computational results are compared to each other, and their accuracy is evaluated.

  DOI：

  10.1021/ja953796o

文献信息

• β-Cyanoethyl Anion:  Lusus Naturae
  作者：Grant N. Merrill、Gregg D. Dahlke、Steven R. Kass

  DOI：10.1021/ja953796o

  日期：1996.1.1

  A stable E1(cb) intermediate, beta-cyanoethyl anion (1 beta), has been synthesized in the gas phase at room temperature under thermal conditions via the fluoride-induced desilylation of 3-(trimethylsilyl)propionitrile. The reactivity and thermodynamic properties of this ion are reported. The cyano group is found to lower the proton affinity of 1 beta by 29 +/- 6 kcal/mol, which represents a particularly large substituent effect. High-level ab initio and density functional calculations have been carried out on 1 beta and several related species. The computational results are compared to each other, and their accuracy is evaluated.