Succinimidyl-Radikal | 24344-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: Succinimidyl-Radikal
• 英文别名: Succinimido
• CAS: 24344-83-0
• 化学式: C₄H₄NO₂
• 分子量: 98.0813
• InChiKey: HCXJFMDOHDNDCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Succinimidyl-Radikal 在 钌 作用下， 生成 succinimide anion
  参考文献：
  名称：

  水中琥珀酰亚胺基团的单电子还原势和开环

  摘要：

  By means of pulse radiolysis in water, N-chlorosuccinimide (SCl) was reduced in a one-electron step to yield the succinimidyl radical, S., via the intermediacy of the radical anion, SCl.-. The rate of ring opening of S. was measured to be 8 x 10(4) s-1. By equilibration with Cl2.-/2Cl-, the one-electron reduction potential of S. was determined to be 2.22 +/- 0.02 V vs NHE. From this value and other data, the N-H bond strength in succinimide was calculated to be 118 +/- 3 kcal/mol.

  DOI：

  10.1021/j100110a023
• 作为产物：
  描述：

  N-氯代丁二酰亚胺 在 盐酸 、 氧气 作用下， 以 水 为溶剂， 生成 Succinimidyl-Radikal
  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

• Cyclisation of ω-(isocyanatocarbonyl)alkyl radicals: acyclic precursors of imidyl radicals
  作者：Parveen Kaushal、Brian P. Roberts

  DOI：10.1039/p29890001559

  日期：——

  2,2-dimethylsuccinimidyl radical which subsequently undergoes rin opening to yield Me2ĊCH2C(O)NCO (15). The overall rearrangement of (14) to (15) represents 1,2-shift of the –C(O)NCO group via an intermediate imidyl radical. The glutarimidyl radical is forme by 1,6-endo cyclisation of H2ĊCH2CH2C(O)NCO. It is proposed that the rapid cyclisation of ω-isocyanatoalkyl radicals provides strong evidence

  由N-卤代亚胺的光解或卤素原子的提取生成的亚胺基自由基在Bu 2 t C CH 2的有效捕集下得到了相对持久的加合物，这已通过es光谱学进行了研究。溴原子抽象从BRCH 2 CH 2 C（O）NCO（2）得到ħ 2 CCH 2 C（O）NCO（1），其经历快速1,5-内切环化，得到琥珀酰亚胺基团。已使用esr光谱结合Bu 2 t C CH 2的自旋阱对这种环化进行了研究。和BU吨Ñ O.为（环化率系数1）已被估计为3.7×10 6小号-1在环己烷328ķ从（之间的自由基链式反应的产物的分析2）的triethylgermane。ESR和产物的分析研究表明，ħ 2 CCME 2 C（O）NCO（14）cyclises，MOR速度比（1），得到2,2- dimethylsuccinimidyl基团，其随后经历RIN开口，得到我2 CCH 2 Ç （O）NCO（15）。（14）至（15）的整体重排
• Reaction of phenylchlorocarbene and diphenylcarbene with the carbon-chlorine bond: kinetics and mechanisms
  作者：Michelle B. Jones、Vincent M. Maloney、Matthew S. Platz

  DOI：10.1021/ja00032a034

  日期：1992.3

  The reactions of phenylchlorocarbene (PCC) and diphenylcarbene (DPC) with carbon-chlorine bonds were investigated by laser flash photolysis techniques, product studies, and electrochemical methods. The data with both carbenes are consistent with a polar chlorine atom transfer to form radical pairs. The PCC reaction can be thought of as an inner sphere electron transfer from the carbene to the carbon-halogen

  通过激光闪光光解技术、产物研究和电化学方法研究了苯基氯卡宾 (PCC) 和二苯基卡宾 (DPC) 与碳-氯键的反应。两种卡宾的数据与极性氯原子转移形成自由基对一致。PCC 反应可以被认为是从卡宾到碳卤键的内球电子转移，其中在过渡态中形成了部分碳卤键。过渡态被认为涉及闭壳和开壳单线态表面之间的交叉。DPC 与氯供体反应获得的数据类似于 PCC 获得的数据，但更难以解释，因为与 C-Cl 键反应的状态的多样性尚不清楚。40 个参考文献，10 个图，9 个标签。
• One-electron reduction of N-bromosuccinimide. Rapid expulsion of a bromine atom
  作者：Johan Lind、Xinhua Shen、Trygve E. Eriksen、Gabor Merenyi、Lennart Eberson

  DOI：10.1021/ja00012a035

  日期：1991.6

  By means of pulse radiolysis N-bromosuccinimide, SBr, was reduced to its radical anion, SBr .− . Evidence is presented that SBr .− rapidly fragments into the succinimide anion, S − , and a free bromine atom, Br . , which is converted into Br 2 •− by reacting with Br − present. The rate constant of hydrogen abstraction by Br . from 2-propanol and methanol have been determined. The carbon-centered radical

  通过脉冲辐射分解，N-溴代琥珀酰亚胺 SBr 被还原为其自由基阴离子 SBr .- 。有证据表明 SBr .- 迅速分裂成琥珀酰亚胺阴离子 S - 和游离溴原子 Br 。，通过与存在的 Br - 反应转化为 Br 2 •-。Br 夺氢的速率常数。已从 2-丙醇和甲醇中测定。还发现叔丁醇的碳中心自由基在 Br - 存在下与 SBr 2 .- 反应
• Electrochemical reduction of N-bromosuccinimide. Reaction mechanism for formation of the succinimidyl radical
  作者：John E. Barry、Manuel Finkelstein、W. Michael Moore、Sidney D. Ross、Lennart Eberson、Lennart Joensson

  DOI：10.1021/jo00346a026

  日期：1982.3
• ESR single-crystal study of the succinimidyl .pi.-electron radical in x-irradiated succinimide at 26 K
  作者：A. Lund、P. O. Samskog、L. Eberson、S. Lunell

  DOI：10.1021/j100210a044

  日期：1982.6