乙酰氟烯醇阴离子 | 64723-98-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 乙酰氟烯醇阴离子
• 英文名称: acetyl fluoride enolate anion
• 英文别名: acetyl fluoride; deprotonated form；1-fluoro-ethenolate
• CAS: 64723-98-4
• 化学式: C₂H₂FO
• 分子量: 61.0357
• InChiKey: DLZHJQBWMXWVBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  4.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6,6-二甲基-5-亚甲基-1,3-环戊二烯 、 乙酰氟烯醇阴离子 以13%的产率得到6,6-dimethylfulvene anion
  参考文献：
  名称：

  Gas-phase Broensted versus Lewis acid-base reactions of 6,6-dimethylfulvene. A sensitive probe of the electronic structures of organic anions

  摘要：

  DOI：

  10.1021/ja00217a002
• 作为产物：
  描述：

  乙酸乙酯 在 氦气 、 氢氟酸 作用下， 24.85 ℃ 、66.66 Pa 条件下， 以54%的产率得到乙酰氟烯醇阴离子
  参考文献：
  名称：

  流动余辉研究某些甲酰基，乙酰基和环状酯的气相亲核反应

  摘要：

  在流动的余辉中，已经研究了多种亲核试剂与气相中甲酰基和乙酰基酯的反应。气相中所允许的反应比冷凝相中所见的反应变化更大。甲基和乙基酯以及各种内酯的反应的速率已进行与各种亲核试剂：H 2 Ñ -，HO -，CH 3 ö -，NCCH 2 -，F -，CH 3 C（O）CH 2 -，CH 3 S –和O 2 NCH 2 –。例如，已发现NCCH 2 –  + HCO 2 CH 2 CH 3的反应速率为（1.3±0.2）×10 –10 cm 3分子–1 s –1，唯一的产物是HC（O –）CHCN这是由于亲核酰基取代（B AC 2），然后在离子-分子络合物中进行质子转移所致。已经观察到的其他反应机理包括β-消除（E2），烷基上的双分子亲核取代（BAL 2）和Riveros反应（消除CO）。F –  + HCO 2的机制已在B3LYP / 6-31 + G（d）水平确定了CH 3反应。最值得注意的是，通道是通过计算确定的（BAL

  DOI：

  10.1039/a905632g

文献信息

• A comprehensive view of the gas-phase reaction of fluoride ions and acetic acid derivatives
  作者：Jose M. Riveros

  DOI：10.1039/c39900000773

  日期：——

  The gas-phase reaction of F– with several acetic acid derivatives (MeCOX) is shown to proceed primarily by proton abstraction in the collision complex, rather than nucleophilic displacement, leading to the facile formation of FHX– or CH2CFO–.

  结果表明，F –与几种乙酸衍生物（MeCOX）的气相反应主要是通过质子在碰撞复合物中的提取而不是亲核取代进行的，从而导致FHX –或CH 2 CFO –的容易形成。
• Fragmentation reactions of some aliphatic esters in the NCl(F−) and NCl(NH2−) mass spectra
  作者：Hans-Fr. Grützmacher、Barbara Grotemeyer

  DOI：10.1002/oms.1210190305

  日期：1984.3

  AbstractThe NCI(F−) and NCI(NH2−) mass spectra of a series of aliphatic acetates and of methyl and ethyl trimethylacetate have been obtained. The formation of fluoroenolate ions CH2COF− and of carboxamide anions RCONH− (R  CH3))CH3C). respectively, is observed besides formation of [M  H]− ions and carboxylate ions RCOO− (R  CH3, (CH3)3C). The relative intensities of the different anions depend on the structure of the ester molecules and on the primary reactant anions. Usually, the NCI(NH2−) spectra of the acetates are dominated by [M  H]− ions ([MD]− ions in the case of trideuteroacetates) fragmenting unimolecularly by elimination of an alcohol. The carboxylate ions are important fragments, too, but carboxamide ions are only observed with large intensities in the NCI(NH2− spectra of the trimethylacetates. The NCI(F−) spectra show much larger intensities of carboxylate ions and fluoroenolate ions. The mechanisms of the fragmentation reactions are discussed. The results indicate that most or even all of the fragment ions in the NCI(F− mass spectra of aliphatic esters are formed by addition‐elimination reactions via a tetrahedral intermediate, while competition between direct proton abstraction and addition‐elimination reactions occurs in the NCI(NH2−) mass spectra because of the higher basicity of NH2− resulting in an early transition state for direct proton abstraction.