ortho-ethylbenzoic acid carboxylate anion | 43-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ortho-ethylbenzoic acid carboxylate anion
• 英文别名: 2-Ethylbenzoate
• CAS: 43-89-0
• 化学式: C₉H₉O₂
• 分子量: 149.169
• InChiKey: CGMMPMYKMDITEA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ortho-ethylbenzoic acid carboxylate anion 生成 ortho-ethylphenyl anion
  参考文献：
  名称：

  On the generation and characterization of the spiro[2,5]octadienyl anion in the gas phase

  摘要：

  AbstractThree routes have been explored in both a high‐pressure chemical ionization (CI) source and a low‐pressure Fourier transform ion cyclotron resonance (FT‐ICR) cell to generate the spiro[2,5]octadienyl anion in the gas phase: (i) proton abstraction from spiro[2,5]octa‐4,6‐diene; (ii) expulsion of trimethysilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2‐phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3‐phenylpropanoic acid via carbon dioxide loss. From comparison of the CID spectra of various reference [C8H9]− ions with those of the [C8H9]− ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a [C8H9]−ion whose CID spectrum is not inconsistent with the one expected for the spiro[2,5]octadienyl anion. In the FT‐ICR cell [C8H9]− ions are generated along all three routes; their structures have been identified by specific ion‐molecule reactions and appear to be different. Route (i) yields an α‐methyl benzyl anion, probably due to isomerization within the ion‐molecule complex formed. An ortho‐ethylphenyl anion is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2‐phenylethyl primary carbanion. The [C8H9]− ion formed along route (iii) shows reactions similar to those of the 1,1‐dimethylcyclohexadienyl anion which is structurally related to the spiro[2,5]octadienyl anion. Furthermore, the [C8H9]− ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms. On the basis of all these observations it is therefore quite likely that the spiro[2,5]octadienyl anion is formed by collisionally induced decarboxylation of the 3‐phenylpropanoic acid carboxylate anion and can be a long‐lived and stable species in the gas phase.

  DOI：

  10.1002/oms.1210240807

文献信息

• On the generation and characterization of the spiro[2,5]octadienyl anion in the gas phase
  作者：Wilfrid P. M. Maas、Peter A. Van Veelen、Nico M. M. Nibbering

  DOI：10.1002/oms.1210240807

  日期：1989.8

  AbstractThree routes have been explored in both a high‐pressure chemical ionization (CI) source and a low‐pressure Fourier transform ion cyclotron resonance (FT‐ICR) cell to generate the spiro[2,5]octadienyl anion in the gas phase: (i) proton abstraction from spiro[2,5]octa‐4,6‐diene; (ii) expulsion of trimethysilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2‐phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3‐phenylpropanoic acid via carbon dioxide loss. From comparison of the CID spectra of various reference [C8H9]− ions with those of the [C8H9]− ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a [C8H9]−ion whose CID spectrum is not inconsistent with the one expected for the spiro[2,5]octadienyl anion. In the FT‐ICR cell [C8H9]− ions are generated along all three routes; their structures have been identified by specific ion‐molecule reactions and appear to be different. Route (i) yields an α‐methyl benzyl anion, probably due to isomerization within the ion‐molecule complex formed. An ortho‐ethylphenyl anion is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2‐phenylethyl primary carbanion. The [C8H9]− ion formed along route (iii) shows reactions similar to those of the 1,1‐dimethylcyclohexadienyl anion which is structurally related to the spiro[2,5]octadienyl anion. Furthermore, the [C8H9]− ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms. On the basis of all these observations it is therefore quite likely that the spiro[2,5]octadienyl anion is formed by collisionally induced decarboxylation of the 3‐phenylpropanoic acid carboxylate anion and can be a long‐lived and stable species in the gas phase.