(E)-fluoro-acetone oxime

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-fluoro-acetone oxime
• 英文别名: (E)-fluoroacetoxime
• 化学式: C₃H₆FNO
• 分子量: 91.0851
• InChiKey: UIVYJELOMTZOGM-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (Z)-fluoro-acetone oxime 以 氘代氯仿 为溶剂， 生成 (E)-fluoro-acetone 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

• Conformational analysis of fluoroacetoxime and of itsO-methyl ether by1H,13C and15N NMR and theoretical calculations
  作者：Cláudio F. Tormena、Roberto Rittner、Raymond J. Abraham、Ernani A. Basso、Barbara C. Fiorin

  DOI：10.1002/poc.682

  日期：2004.1

  The solvent dependence of the 1H, 13C and 15N NMR spectra of (E)-fluoroacetoxime [(E)-FAO] and of (E)-fluoroacetoxime O-methyl ether [(E)-FAOME], was examined and the HF, CF and NF couplings are reported. Density functional theory (DFT) at the B3LYP/6–311++g(2df,2p) level with ZPE (zero point energy) correction was used to obtain the rotamer geometries. In both (E)-FAO and (E)-FAOME the DFT method

  检查了（E）-氟代肟基[（E）-FAO]和（E）-氟代肟基O-甲基醚[（E）-FAOME]的1 H，13 C和15 N NMR光谱的溶剂依赖性，并报告了HF，CF和NF耦合。使用ZPE（零点能量）校正在B3LYP / 6–311 ++ g（2df，2p）级别的密度泛函理论（DFT）来获得旋转异构体的几何形状。在这两种（ë）-FAO和（Ë）-FAOME的DFT方法，得到对应于所述两个能量最小值顺（F-C-C N，0°）和笨拙（F-C-CN，124.1°）旋转木马。相反，在（Z）-FAO中，DFT方法仅给出了与反式旋转异构体相对应的最小能量。通过溶剂化理论分析了（E）-FAO中的4 J HF和1 J CF偶合，假定顺式和薄纱形式以汽相形式存在，在CCl 4中降至1.54 kcal mol -1，在-1.19 kcal mol -1时降低在DMSO中（1 kcal = 4.184 kJ。在（E）
• 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.