propionyl cation | 35696-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: propionyl cation
• 英文别名: Propanoyl cation；Ethyloxocarbenium ion；Propylidyne-oxonium；propan-1-one
• CAS: 35696-65-2
• 化学式: C₃H₅O
• 分子量: 57.0721
• InChiKey: IXRIKXJQFYIWSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  propionyl cation 在 丙酮 作用下， 生成 甲基乙烯酮
  参考文献：
  名称：

  Thermokinetic Determination of Gas-Phase Basicities. Application to Ketene, Methylketene, and Formaldimine

  摘要：

  Rate constants have been determined for proton transfer reactions of the type [MH](+) + B reversible arrow M + [BH](+), where M is ketene, methylketene, and formaldimine and B is a reference base. A quantitative relationship between the rate constant and the free energy (or enthalpy) of the reaction allows the determination of the gas-phase basicity, GB, (or proton affinity, PA) of M. This thermokinetic method gives results comparable to that obtained from equilibrium constant measurements. The values derived for ketene, methylketene, and formaldimine follow: GB(ketene) = 788 +/- 3 kJ/mol, PA(ketene) = 817 +/- 3 kJ/mol; GB(methylketene) = 809 +/- 3 kJ/mol, PA(methylketene)= 842 +/- 3 kJ/mol; GB(formaldimine) = 830 +/- 3 kJ/mol and PA(formaldimine) = 860 +/- 5 kJ/mol. Heats of formation of methylketene and of formaldimine that may be deduced from a combination of these results with literature data are as follows: Delta H-f degrees(300) (CH3CHCO) = -97 +/- 5 kJ/mol and Delta H-f degrees(300) (CH2=NH) = 75 +/- 5 kJ/mol.

  DOI：

  10.1021/jp960761h
• 作为产物：
  描述：

  甲基乙烯酮 在 (CH₃COOCH₃)H+ 作用下， 生成 propionyl cation
  参考文献：
  名称：

  Methylketene. Ion chemistry and proton affinity

  摘要：

  DOI：

  10.1021/ja00535a040
• 作为试剂：
  描述：

  3-巯基丙酸 在 propionyl cation 作用下， 以 gas 为溶剂， 生成 1-thioxopropylium ion
  参考文献：
  名称：

  硫酰离子。硫代和二硫代酸衍生物的气相离子分子反应

  摘要：

  Les 离子 thioacylium CH 3 CS + et C 2 H 5 CS + 子类同相凝视部分 acylium CH 3 CO + et C 2 H 5 CO + et les acides thioacetique et thiopropionique par 共振回旋加速器。De plus, CH 3 CS + est forme aussi a partir du diacetylsulfe。Mecanisme de Formisme des ionic des thioacylium et des reaction de transfert d'acyle et de thioacyle en phasegazeuse

  DOI：

  10.1021/ja00361a026

文献信息

• Oxidation of Alkyl Ions, C<i>_n</i>H₂<i>_n</i>₊₁⁺ (<i>n</i> = 1−5), in Reactions with O₂ and O₃ in the Gas Phase
  作者：Skip Williams、W. B. Knighton、Anthony J. Midey、A. A. Viggiano、Stephan Irle、Qingfang Wang、Keiji Morokuma

  DOI：10.1021/jp031099+

  日期：2004.3.1

  product ion branching fractions are reported for the reactions of CH3+, C2H5+, s-C3H7+, s-C4H9+, t-C4H9+, and t-C5H11+ with O2 and O3 at 300 K in a variable-temperature selected-ion flow tube (VT-SIFT). The reaction rate constant for CH3+ with O3 is large and approximately equal to the thermal energy capture rate constant given by the Su−Chesnavich equation. The C2H5+, s-C3H7+, and s-C4H9+ ions are somewhat

  报告了 CH3+、C2H5+、s-C3H7+、s-C4H9+、t-C4H9+ 和 t-C5H11+ 与 O2 和 O3 在 300 K 温度下在变温选择离子流管中反应的速率常数和产物离子支化分数(VT-SIFT)。CH3+ 与 O3 的反应速率常数很大，大约等于 Su-Chesnavich 方程给出的热能捕获速率常数。C2H5+、s-C3H7+ 和 s-C4H9+ 离子的反应性稍差，反应速率约为热捕获率的 7-46%。HCO+ 和 C2H3O+ 离子是这些反应的主要产物。发现 t-C4H9+ 和 t-C5H11+ 离子没有反应性，速率常数 <5 × 10-12 cm3 s-1，这是我们使用这种臭氧源的仪器的当前检测限。臭氧是基态的单线态，和 B3LYP/6-31G(d) 理论水平的从头算计算表明，可以形成反应物配合物，稳定性随着连接到阳离子碳原子的烷基链的大小而降低。反应性下降...
• Selective carbonylation of propane in HF–SBF₅: control of the activation step via the hydrocarbon/carbon monoxide ratio
  作者：Serge Delavarenne、Michel Simon、Michel Fauconet、Jean Sommer

  DOI：10.1039/c39890001049

  日期：——

  The selectivity of propane carbonylation in HF–SbF5 is found to depend on the propane/CO ratio, and is rationalized in terms of two competing activation processes for the alkane.

  发现在HF–SbF 5中丙烷羰基化的选择性取决于丙烷/ CO比率，并且根据两个相互竞争的烷烃活化过程进行了合理化。
• Nonrandomization of energy in chemically activated 2-butanone ions
  作者：David J. McAdoo、Charles E. Hudson

  DOI：10.1021/j100237a001

  日期：1983.7
• Halogen promoted selective carbonylation of propane in superacid media
  作者：Serge Delavarenne、Michel Simon、Michel Fauconet、Jean Sommer

  DOI：10.1021/ja00183a067

  日期：1989.1
• Thermokinetic Determination of Gas-Phase Basicities. Application to Ketene, Methylketene, and Formaldimine
  作者：Guy Bouchoux、Jean-Yves Salpin

  DOI：10.1021/jp960761h

  日期：1996.1.1

  Rate constants have been determined for proton transfer reactions of the type [MH](+) + B reversible arrow M + [BH](+), where M is ketene, methylketene, and formaldimine and B is a reference base. A quantitative relationship between the rate constant and the free energy (or enthalpy) of the reaction allows the determination of the gas-phase basicity, GB, (or proton affinity, PA) of M. This thermokinetic method gives results comparable to that obtained from equilibrium constant measurements. The values derived for ketene, methylketene, and formaldimine follow: GB(ketene) = 788 +/- 3 kJ/mol, PA(ketene) = 817 +/- 3 kJ/mol; GB(methylketene) = 809 +/- 3 kJ/mol, PA(methylketene)= 842 +/- 3 kJ/mol; GB(formaldimine) = 830 +/- 3 kJ/mol and PA(formaldimine) = 860 +/- 5 kJ/mol. Heats of formation of methylketene and of formaldimine that may be deduced from a combination of these results with literature data are as follows: Delta H-f degrees(300) (CH3CHCO) = -97 +/- 5 kJ/mol and Delta H-f degrees(300) (CH2=NH) = 75 +/- 5 kJ/mol.