N-oxidoethanimine | 140390-74-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-oxidoethanimine
• CAS: 140390-74-5
• 化学式: C₂H₄NO
• 分子量: 58.0599
• InChiKey: FZENGILVLUJGJX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-硝基苯基)二苯基磷酸酯 、 N-oxidoethanimine 在 1-十二烷基-3-甲基咪唑氯盐 、 sodium hydroxide 作用下， 生成 、 4-硝基苯酚阴离子
  参考文献：
  名称：

  胶束催化中的表面活性离子液体：阴离子选择对亲核取代反应速率的影响†

  摘要：

  合成了一系列基于1-十二烷基-3-甲基咪唑鎓阳离子和不同阴离子（例如卤化物和烷基硫酸盐）的表​​面活性离子液体。通过表面张力、电导率测量和紫外-可见光谱来表征这些离子液体在水中的聚集行为，以确定临界胶束浓度 (CMC) 并提供聚集参数。两亲性离子液体的表面活性和聚集特性的测定伴随着对选定的表面活性离子液体的 SAXS 研究。测试了这些具有不同阴离子的表面活性离子液体在亲核取代反应中对有机磷化合物降解的应用。通过紫外-可见分光光度法进行的动力学研究表明，与纯水相比，胶束系统中的反应强烈加速。此外，还观察到阴离子的影响，导致与胶束结合的阴离子与反应速率常数之间存在相关性，表明仔细选择表面活性离子液体可以显着影响反应结果。

  DOI：

  10.1039/c6cp00493h
• 作为产物：
  描述：

  亚硝酸甲酯 、 丙醛烯醇阴离子 以52.9%的产率得到N-oxidoethanimine
  参考文献：
  名称：

  Anion Structure Determination in the Gas Phase:  Chemical Reactivity as a Probe

  摘要：

  In the gas phase, the discrimination between two isomeric anion structures is a challenge that requires different solutions for different applications. The anionic oxy-Cope rearrangement involves the rearrangement of an alkoxide to an isomeric enolate; the mechanistic study of such a process in the gas phase requires a simple and selective probe process. Using a flowing afterglow mass spectrometer, we have examined the utility and limitations of using chemical reactivity to discriminate between alkoxides and enolates in the gas phase. A series of alkoxides and enolates were allowed to react with three chemical probe reagents: methanol-O-d, methyl nitrite, and dimethyl disulfide. Quantitative and qualitative characterization of each probe reagent reveals the especially broad and flexible utility of dimethyl disulfide as a chemical probe. Dimethyl disulfide is a selective reagent with ambident behavior that reacts efficiently with all anions studied and fully capitalizes on the structure/reactivity differences between alkoxides and enolates. Alkoxides behave as classical ''hard bases'' when allowed to react with dimethyl disulfide, effecting elimination across the C-S bond, whereas enolates, ''soft bases'', attack at sulfur. Methyl nitrite is also a selective ambident probe reagent but, due to its particularly slow reaction with enolates, is useful only in conjunction with a more reliable probe such as dimethyl disulfide. Methanol-O-d, for a variety of reasons detailed in the paper, is unsuitable as a chemical probe reagent for the unequivocal discernment between alkoxides and enolates.

  DOI：

  10.1021/jo961463j

文献信息

• Kinetic study of the reactions of<i>p</i>-nitrophenyl acetate and<i>p</i>-nitrophenyl benzoate with oximate nucleophiles
  作者：Shuchi Tiwari、Sancheeta Kolay、Kallol K. Ghosh、Kamil Kuca、Jan Marek

  DOI：10.1002/kin.20363

  日期：2009.1

  The reactions of p‐nitrophenyl acetate (PNPA) and p‐nitrophenyl benzoate (PNPB) with α‐nucleophile oximates, that is, butane 2,3‐dione monoximate, pralidoximate, and other oximates have been studied in the presence of different cationic surfactants. The first‐order rate constant increases with increasing surfactant concentration. The extent of acceleration is dependent on the head group structure of

  在不同阳离子表面活性剂存在下，研究了乙酸对硝基苯酯（PNPA）和对硝基苯甲酸苯酯（PNPB）与α-亲核肟酸酯的反应，即2,3-二酮丁烷单肟酸酯，对羟基苯甲酸酯和其他肟酸酯的反应。 。一级速率常数随表面活性剂浓度的增加而增加。加速程度取决于表面活性剂的头基结构。在较高的表面活性剂浓度下，PNPA对所有亲核试剂的反应性均比PNPB高。©2008 Wiley Periodicals，Inc.国际化学杂志Kinet 41：57–64，2009
• Surface-active ionic liquids in micellar catalysis: impact of anion selection on reaction rates in nucleophilic substitutions
  作者：Alice Cognigni、Peter Gaertner、Ronald Zirbs、Herwig Peterlik、Katharina Prochazka、Christian Schröder、Katharina Bica

  DOI：10.1039/c6cp00493h

  日期：——

  anions was tested in nucleophilic substitution reactions for the degradation of organophosphorus compounds. Kinetic studies via UV-Vis spectrophotometry showed a strong acceleration of the reaction in the micellar system compared to pure water. In addition, an influence of the anion was observed, resulting in a correlation between the anion binding to the micelle and the reaction rate constants, indicating

  合成了一系列基于1-十二烷基-3-甲基咪唑鎓阳离子和不同阴离子（例如卤化物和烷基硫酸盐）的表​​面活性离子液体。通过表面张力、电导率测量和紫外-可见光谱来表征这些离子液体在水中的聚集行为，以确定临界胶束浓度 (CMC) 并提供聚集参数。两亲性离子液体的表面活性和聚集特性的测定伴随着对选定的表面活性离子液体的 SAXS 研究。测试了这些具有不同阴离子的表面活性离子液体在亲核取代反应中对有机磷化合物降解的应用。通过紫外-可见分光光度法进行的动力学研究表明，与纯水相比，胶束系统中的反应强烈加速。此外，还观察到阴离子的影响，导致与胶束结合的阴离子与反应速率常数之间存在相关性，表明仔细选择表面活性离子液体可以显着影响反应结果。
• Anion Structure Determination in the Gas Phase:  Chemical Reactivity as a Probe
  作者：Jeehiun K. Lee、Joseph J. Grabowski

  DOI：10.1021/jo961463j

  日期：1996.1.1

  In the gas phase, the discrimination between two isomeric anion structures is a challenge that requires different solutions for different applications. The anionic oxy-Cope rearrangement involves the rearrangement of an alkoxide to an isomeric enolate; the mechanistic study of such a process in the gas phase requires a simple and selective probe process. Using a flowing afterglow mass spectrometer, we have examined the utility and limitations of using chemical reactivity to discriminate between alkoxides and enolates in the gas phase. A series of alkoxides and enolates were allowed to react with three chemical probe reagents: methanol-O-d, methyl nitrite, and dimethyl disulfide. Quantitative and qualitative characterization of each probe reagent reveals the especially broad and flexible utility of dimethyl disulfide as a chemical probe. Dimethyl disulfide is a selective reagent with ambident behavior that reacts efficiently with all anions studied and fully capitalizes on the structure/reactivity differences between alkoxides and enolates. Alkoxides behave as classical ''hard bases'' when allowed to react with dimethyl disulfide, effecting elimination across the C-S bond, whereas enolates, ''soft bases'', attack at sulfur. Methyl nitrite is also a selective ambident probe reagent but, due to its particularly slow reaction with enolates, is useful only in conjunction with a more reliable probe such as dimethyl disulfide. Methanol-O-d, for a variety of reasons detailed in the paper, is unsuitable as a chemical probe reagent for the unequivocal discernment between alkoxides and enolates.