glutarimidyl radical | 94694-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: glutarimidyl radical
• CAS: 94694-72-1
• 化学式: C₅H₆NO₂
• 分子量: 112.108
• InChiKey: WMSMIDFZPYCCJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  glutarimidyl radical 在 氢溴酸 、 一氧化二氮 、 叔丁醇 作用下， 以 水 为溶剂， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The Return of the Succinimidyl Radical.

  摘要：

  The aqueous kinetics of the succinimidyl radical. S-. has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S-. and its ring-opened analogue, the beta B-(isocyanatocarbonyl)ethyl radical, PI.. The equilibrium constant K-1, is ca, 10, with k(1) approximate to 10(7) s(-1) and k(-1) approximate to 10(6) s(-1). The glutarimidyl radical, G(.), was produced by one-electron reduction of N-chloroglutarimide, GCI. The rate constants of several oxidation and hydrogen abstraction reactions with S-. and G(.) have been determined. Furthermore. halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong beta-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI. radical appears to be solvent-insensitive, the ring opening rate of S-., k(1), is estimated to be ca. 100 times faster in, e.g., CH2Cl2, than in water. This suggests hydrogen-bonded stabilisation of S-..

  DOI：

  10.3891/acta.chem.scand.52-0062
• 作为产物：
  描述：

  1-chloropiperidine-2,6-dione 在 e^(1-)(aq) 作用下， 以 水 为溶剂， 生成 glutarimidyl radical
  参考文献：
  名称：

  The Return of the Succinimidyl Radical.

  摘要：

  The aqueous kinetics of the succinimidyl radical. S-. has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S-. and its ring-opened analogue, the beta B-(isocyanatocarbonyl)ethyl radical, PI.. The equilibrium constant K-1, is ca, 10, with k(1) approximate to 10(7) s(-1) and k(-1) approximate to 10(6) s(-1). The glutarimidyl radical, G(.), was produced by one-electron reduction of N-chloroglutarimide, GCI. The rate constants of several oxidation and hydrogen abstraction reactions with S-. and G(.) have been determined. Furthermore. halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong beta-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI. radical appears to be solvent-insensitive, the ring opening rate of S-., k(1), is estimated to be ca. 100 times faster in, e.g., CH2Cl2, than in water. This suggests hydrogen-bonded stabilisation of S-..

  DOI：

  10.3891/acta.chem.scand.52-0062

文献信息

• The Return of the Succinimidyl Radical.
  作者：Gábor Merényi、Johan Lind、Lennart Eberson、Björn Åkermark、John H. Wagenknecht、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0062

  日期：——

  The aqueous kinetics of the succinimidyl radical. S-. has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S-. and its ring-opened analogue, the beta B-(isocyanatocarbonyl)ethyl radical, PI.. The equilibrium constant K-1, is ca, 10, with k(1) approximate to 10(7) s(-1) and k(-1) approximate to 10(6) s(-1). The glutarimidyl radical, G(.), was produced by one-electron reduction of N-chloroglutarimide, GCI. The rate constants of several oxidation and hydrogen abstraction reactions with S-. and G(.) have been determined. Furthermore. halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong beta-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI. radical appears to be solvent-insensitive, the ring opening rate of S-., k(1), is estimated to be ca. 100 times faster in, e.g., CH2Cl2, than in water. This suggests hydrogen-bonded stabilisation of S-..