malononitrile bis-ketenimine tautomer | 20815-46-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: malononitrile bis-ketenimine tautomer
• 英文别名: propadienediylidenediamine；1,2-Propadiene-1,3-diimine
• CAS: 20815-46-7
• 化学式: C₃H₂N₂
• 分子量: 66.0623
• InChiKey: WTJRKYUPEQNLPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-amino-4-cyanoisoxazole 生成 malononitrile bis-ketenimine tautomer
  参考文献：
  名称：

  Formation and identification of ionized and neutral cumulenes, RNCCCNH, by tandem mass spectrometry

  摘要：

  AbstractUsing a combination of mass spectrometric techniques, it is shown that 5‐amino‐4‐cyanoisoxazole molecular ions (1+˙), lose isocyanic acid HNO, not fulminic acid, HCN → O. Metastable ion fragmentations (unimolecular and collision induced) and deuterium‐labelling experiments are in agreement with the formation of a cumulenic structure, HNCCCNH (3a+˙). The hitherto unreported molecules HNCCCNH are also shown to be stable when formed in the low‐pressure gas phase of the mass spectrometer by using the technique of neutralization–reionization mass spectrometry. The arguments developed for the characterization of 3a+˙ have also been extended to the methylated and phenylated analogues 3b+˙ and 3c+˙ [RNCCCNH+˙, R = CH3 or C6H5]. On flash‐vacuum pyrolysis at 700°C, 1 also loses HNCO producing the cumulene 3a, which is in turn readily tautomerized into malononitrile via wall collisions.

  DOI：

  10.1002/oms.1210281030

文献信息

• Formation and identification of ionized and neutral cumulenes, RNCCCNH, by tandem mass spectrometry
  作者：Robert Flammang、Sophie Laurent、Monique Flammang-Barbieux、Curt Wentrup

  DOI：10.1002/oms.1210281030

  日期：1993.10

  AbstractUsing a combination of mass spectrometric techniques, it is shown that 5‐amino‐4‐cyanoisoxazole molecular ions (1+˙), lose isocyanic acid HNO, not fulminic acid, HCN → O. Metastable ion fragmentations (unimolecular and collision induced) and deuterium‐labelling experiments are in agreement with the formation of a cumulenic structure, HNCCCNH (3a+˙). The hitherto unreported molecules HNCCCNH are also shown to be stable when formed in the low‐pressure gas phase of the mass spectrometer by using the technique of neutralization–reionization mass spectrometry. The arguments developed for the characterization of 3a+˙ have also been extended to the methylated and phenylated analogues 3b+˙ and 3c+˙ [RNCCCNH+˙, R = CH3 or C6H5]. On flash‐vacuum pyrolysis at 700°C, 1 also loses HNCO producing the cumulene 3a, which is in turn readily tautomerized into malononitrile via wall collisions.