pentan-3-one, deprotonated form | 29263-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pentan-3-one, deprotonated form
• 英文别名: pentan-3-one; deprotonated form；pent-2-en-3-olate；3-Pentanon enolat
• CAS: 29263-72-7
• 化学式: C₅H₉O
• 分子量: 85.1259
• InChiKey: DIFUHTVNCOXBKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  6.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  环己三烯 、 pentan-3-one, deprotonated form 生成 2-phenylpentan-3-one
  参考文献：
  名称：

  The SRN1 Reaction: An Attempt to Calculate the Thermodynamic Driving Force for the Addition of Nucleophiles to Phenyl Radical.

  摘要：

  Phenyl radical is formed in the propagation chain of the aromatic SRN 1 reaction from cleavage of the radical anion of the precursor phenyl halide (PhX.-); subsequent addition of nucleophile Y- to Ph-. yields the radical anion of the substitution product (PhY.-). In this addition step, transfer of an electron from the nucleophile to Ph-. is concerted with bond formation, and the extra electron of the new two-center three-electron bond is, in general, located in a pi* MO of the aromatic moiety. Three factors mainly affect the efficiency of this addition step: (i) the energy of the new Ph-Y bond; (ii) the stability of the radical anion of the substitution product; (iii) the oxidation potential of the nucleophile. In keeping with these points, the energy of some Ph-Y bonds has been calculated, and the oxidation potential of Y- species, along with the reduction potential of the related PhY substitution products, have been determined. Calculation of the thermodynamic driving force of the nucleophile/radical addition step is reported for some significant nucleophiles. Finally, comparison of the thermodynamic driving force with experimental reactivity of the same nucleophile in the addition step is attempted.

  DOI：

  10.3891/acta.chem.scand.52-0067
• 作为产物：
  描述：

  3-ethylpentan-3-olate 生成 乙烷 、 pentan-3-one, deprotonated form
  参考文献：
  名称：

  气相负离子单分子分解的机理研究。醇盐阴离子

  摘要：

  Les ion alcoolates subissent une demoles neutres pour donner des ions enolates

  DOI：

  10.1021/ja00217a003

文献信息

• Mercer, Roger S.; Harrison, Alex G., Canadian Journal of Chemistry, 1988, vol. 66, p. 2947 - 2953
  作者：Mercer, Roger S.、Harrison, Alex G.

  DOI：——

  日期：——
• Mechanistic studies on gas-phase negative ion unimolecular decompositions. Alkoxide anions
  作者：William. Tumas、Robert F. Foster、John I. Brauman

  DOI：10.1021/ja00217a003

  日期：1988.4

  Les ions alcoolates subissent une elimination de molecules neutres pour donner des ions enolates

  Les ion alcoolates subissent une demoles neutres pour donner des ions enolates
• The SRN1 Reaction: An Attempt to Calculate the Thermodynamic Driving Force for the Addition of Nucleophiles to Phenyl Radical.
  作者：Carlo Galli、Patrizia Gentili、Lian Zhang、Björn Åkermark、John H. Wagenknecht、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0067

  日期：——

  Phenyl radical is formed in the propagation chain of the aromatic SRN 1 reaction from cleavage of the radical anion of the precursor phenyl halide (PhX.-); subsequent addition of nucleophile Y- to Ph-. yields the radical anion of the substitution product (PhY.-). In this addition step, transfer of an electron from the nucleophile to Ph-. is concerted with bond formation, and the extra electron of the new two-center three-electron bond is, in general, located in a pi* MO of the aromatic moiety. Three factors mainly affect the efficiency of this addition step: (i) the energy of the new Ph-Y bond; (ii) the stability of the radical anion of the substitution product; (iii) the oxidation potential of the nucleophile. In keeping with these points, the energy of some Ph-Y bonds has been calculated, and the oxidation potential of Y- species, along with the reduction potential of the related PhY substitution products, have been determined. Calculation of the thermodynamic driving force of the nucleophile/radical addition step is reported for some significant nucleophiles. Finally, comparison of the thermodynamic driving force with experimental reactivity of the same nucleophile in the addition step is attempted.