C-methylnitrilimine

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: C-methylnitrilimine
• 英文别名: methyl nitrile imine；Ethylidyneazaniumylazanide；ethylidyneazaniumylazanide
• 化学式: C₂H₄N₂
• 分子量: 56.0672
• InChiKey: VZINGKJEDFOIII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  5.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  C-methylnitrilimine 反应 0.03h， 生成 3-methyl-1H-diazirine
  参考文献：
  名称：

  Generation and Characterization of a 4π-Electron Three-Membered Ring 1H-Diazirine: An Elusive Intermediate in Nitrile Imine–Carbodiimide Isomerization

  摘要：

  The photolysis at 222 nm of 5-methyltetrazole isolated in a cryogenic argon matrix leads to formation of methyl nitrile innine as primary product. Subsequent irradiation at 328 nm induces transformation of the nitrile imine into 4 pi-electron three-membered-ring 3-methyl-1H-diazirine, which photorearranges to give methyl carbodiimide. These products were characterized by IR spectroscopy and theoretical calculations. For the first time, a 1H-diazirine was captured as intermediate in the photoisomerization of nitrile imines into carbodiimides.

  DOI：

  10.1021/jo402744f
• 作为产物：
  描述：

  5-甲基四氮唑 反应 0.02h， 生成 N-methylcarbodiimide 、 C-methylnitrilimine
  参考文献：
  名称：

  Generation and Characterization of a 4π-Electron Three-Membered Ring 1H-Diazirine: An Elusive Intermediate in Nitrile Imine–Carbodiimide Isomerization

  摘要：

  The photolysis at 222 nm of 5-methyltetrazole isolated in a cryogenic argon matrix leads to formation of methyl nitrile innine as primary product. Subsequent irradiation at 328 nm induces transformation of the nitrile imine into 4 pi-electron three-membered-ring 3-methyl-1H-diazirine, which photorearranges to give methyl carbodiimide. These products were characterized by IR spectroscopy and theoretical calculations. For the first time, a 1H-diazirine was captured as intermediate in the photoisomerization of nitrile imines into carbodiimides.

  DOI：

  10.1021/jo402744f

文献信息

• Photochemical transformations of 5-methyltetrazole. Matrix isolation FTIR and DFT studies
  作者：M. Pagacz-Kostrzewa、J. Krupa、M. Wierzejewska

  DOI：10.1016/j.jphotochem.2013.12.011

  日期：2014.3

  In situ photolysis of 5-methyltetrazole (MT) isolated in low temperature argon matrices was induced by tunable UV laser radiation. The progress of the reactions was followed by FTIR spectroscopy that allowed for spectroscopic identification of three photoproducts resulting from the MT ring cleavage, namely C-methylnitrilimine CH3CNNH, N-methylcarbodiimide CH3NCNH, methylcyanamide CH3NHCN. The kinetic

  可调谐的紫外激光辐射可诱导低温氩气中5-甲基四唑（MT）的原位光解。FTIR光谱跟踪反应进程，该光谱可用于光谱鉴定由MT环断裂产生的三种光产物，即C-甲基丁腈CH 3 CNNH，N-甲基碳二亚胺CH 3 NCNH，甲基氰胺CH 3NHCN。这些产品获得的动力学曲线显示了在辐照过程中物质的不同行为。发现N-甲基碳二亚胺分子进一步分解成两个HCN或HNC分子，它们在基质笼中相互作用形成不同的氢键二聚体。量子化学计算（DFT，TD-DFT）支持对观察到的光过程的解释。
• Generation and Characterization of a 4π-Electron Three-Membered Ring 1<i>H</i>-Diazirine: An Elusive Intermediate in Nitrile Imine–Carbodiimide Isomerization
  作者：Cláudio M. Nunes、Cuauhtémoc Araujo-Andrade、Rui Fausto、Igor Reva

  DOI：10.1021/jo402744f

  日期：2014.4.18

  The photolysis at 222 nm of 5-methyltetrazole isolated in a cryogenic argon matrix leads to formation of methyl nitrile innine as primary product. Subsequent irradiation at 328 nm induces transformation of the nitrile imine into 4 pi-electron three-membered-ring 3-methyl-1H-diazirine, which photorearranges to give methyl carbodiimide. These products were characterized by IR spectroscopy and theoretical calculations. For the first time, a 1H-diazirine was captured as intermediate in the photoisomerization of nitrile imines into carbodiimides.