Trifluoropropionic acid sodium salt

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Trifluoropropionic acid sodium salt
• 英文别名: sodium 3,3,3-trifluoropropanoate；Sodium;3,3,3-trifluoropropanoate；sodium;3,3,3-trifluoropropanoate
• 化学式: C₃H₂F₃O₂*Na
• 分子量: 150.033
• InChiKey: CTEGORMZMNTCFV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.31
• 重原子数：
  9
• 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：
  40.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Trifluoropropionic acid sodium salt 在 水 作用下， 生成 三氟乙烷 、 二氧化碳
  参考文献：
  名称：

  Spectroscopy of Hydrothermal Reactions 13. Kinetics and Mechanisms of Decarboxylation of Acetic Acid Derivatives at 100−260 °C under 275 bar

  摘要：

  The rates and pathways of decarboxylation of acetic acid derivatives, RCO2H, and their Na+ salts, RCO2Na, which possess electron-withdrawing groups (R = CCl3-, CF3-, HOC(O)CH2-, NH2C(O)CH2-, CF3CH2-, NCCH2-, CH3C(O)-) were determined in H2O at 100-260 degrees C and a pressure of 275 bar. Simple conversion to RH + CO2 occurs in most cases, except that H2O appears to be a required reactant for the anions. Real-time FTIR spectroscopy was used to determine the rate of formation of CO2 in flow reactors constructed of 316 stainless steel (SS) and of titanium. With a few exceptions, the rate of decarboxylation is similar within the 95% confidence interval in 316 SS and Ti and the difference is smaller than that caused by R. Therefore, while wall effects/catalysis may exist in some cases, it plays a lesser role in the relative rates than the substituent R. The acid form of the keto derivatives decarboxylates more rapidly than the anionic form, whereas the reverse is true for the nonketo derivatives. In keeping with the greater role of H2O as a reactant, the entropy of activation for the anions is smaller or more negative than for the acids. A Taft plot of the decarboxylation rates suggests that the mechanistic details can be interpreted in terms of the various roles of R. Where R = HOC(O)CH2- and NH2C(O)CH2-, decarboxylation occurs faster than expected, probably because a cyclic transition state can exist. The rate is slower than expected for R = CF3-, perhaps because of stabilization of the acid by hyperconjugation. The mechanism of decarboxylation of acids of the remaining R groups is similar and the steric effect of R is somewhat more influential than its electron withdrawing power.

  DOI：

  10.1021/jp984122d
• 作为产物：
  描述：

  1,1,1-trifluoro-3-diazo-2-oxopropane 以 乙醚 为溶剂， 反应 0.25h， 以48%的产率得到Trifluoropropionic acid sodium salt
  参考文献：
  名称：

  重新研究了3-重氮-1,1,1-三氟-2-氧丙烷的光化学Wolff重排。

  摘要：

  2-重氮-4,4,4-三氟乙酰乙酸乙酯（1a）和3-重氮-1,1,1-三氟-2-氧丙烷（1b）在溶液光解中表现出不同的行为（1a的氢提取; 3a的Wolff重排） 1b）[（a）F. Weygand，W。Schwenke和HJ Bestmann，Angew。化学，1958，70，506; （b）F. Weygand，H。Dworschak，K。Koch和S. Konstas，Angew。化学，1961，73，409]。如1b的13C标记所示，这种差异不是由最初形成的α-氧代碳烯重排为具有氢原子作为Wolff重排的迁移取代基的异构体α-氧代碳烯引起的。讨论了从1a生成的单线态α-氧卡宾迅速经历自旋平衡，随后氢脱氢了三重态α-氧卡宾。相反，

  DOI：

  10.1039/b304002j