(Z,E)-iodoacetone oxime | 116668-65-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z,E)-iodoacetone oxime
• 英文别名: (Z)-iodoacetone oxime；iodo-acetone oxime；Jod-aceton-oxim；Jodacetoxim；(NZ)-N-(1-iodopropan-2-ylidene)hydroxylamine
• CAS: 116668-65-6
• 化学式: C₃H₆INO
• 分子量: 198.991
• InChiKey: LAFQLJIJLFXVFY-HYXAFXHYSA-N

物化性质

• 沸点：
  240.3±23.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-碘丙烷-2-酮 在 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (Z,E)-iodoacetone oxime
  参考文献：
  名称：

  Stereochemical and electronic interaction studies of α-heterosubstituted acetone oximes

  摘要：

  The free nu(C=N) bands in the IR spectra of some alpha-heterosubstituted acetone oximes show the existence of only a monomeric form in chloroform solutions at concentrations below 10(-2) M, while in carbon tetrachloride self-associated species are also present. The H-1 and C-13 NMR chemical shift data indicate the predominance of the E over the Z isomer. The Delta nu(C=N), frequency shifts and molecular mechanics calculations strongly suggest that the oximes are in the gauche conformation. X-ray diffraction data have shown that the single dimethylaminoacetone oxime isomer exists in the E configuration and gauche conformation. Non-additivity effects for the ir-methylene carbon chemical shifts seem to indicate the occurrence of a pi(C=N)/sigma(C-X)* interaction besides the pi(C=N)*/sigma(C-X) hyperconjugative interaction.

  DOI：

  10.1016/0584-8539(95)01409-n

文献信息

• Stereochemical and electronic interaction studies of α-heterosubstituted acetone oximes
  作者：P.R Olivato、D.S Ribeiro、R Rittner、Y Hase、D del Pra、G Bombieri

  DOI：10.1016/0584-8539(95)01409-n

  日期：1995.8

  The free nu(C=N) bands in the IR spectra of some alpha-heterosubstituted acetone oximes show the existence of only a monomeric form in chloroform solutions at concentrations below 10(-2) M, while in carbon tetrachloride self-associated species are also present. The H-1 and C-13 NMR chemical shift data indicate the predominance of the E over the Z isomer. The Delta nu(C=N), frequency shifts and molecular mechanics calculations strongly suggest that the oximes are in the gauche conformation. X-ray diffraction data have shown that the single dimethylaminoacetone oxime isomer exists in the E configuration and gauche conformation. Non-additivity effects for the ir-methylene carbon chemical shifts seem to indicate the occurrence of a pi(C=N)/sigma(C-X)* interaction besides the pi(C=N)*/sigma(C-X) hyperconjugative interaction.