2,4-dinitrophenyl octanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,4-dinitrophenyl octanoate
• 英文别名: 2,4-dinitrophenyl n-octanoate；(2,4-Dinitrophenyl) octanoate；(2,4-dinitrophenyl) octanoate
• 化学式: C₁₄H₁₈N₂O₆
• 分子量: 310.307
• InChiKey: WZZQZHLIJFGGHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dinitrophenyl octanoate 在 Sodium laurate 、 抗坏血酸(维生素C) 作用下， 以 水 为溶剂， 生成 2,4-二硝基酚 、 辛酸
  参考文献：
  名称：

  Effects of Sulfobetaine-Sodium Dodecanoate Micelles on Deacylation and Indicator Equilibrium

  摘要：

  Fractional micellar ionization, ct, and critical micelle concentrations have been measured for mixed micelles of sodium dodecanoate (SDOD) and sulfobetaines (C(n)H(2n+1)N(+)Me(2)(CH2)(3)SO3-, SB3-n, n = 10, 12, 14, 16), and values of pH(app) have been calculated from deprotonation of 1-dodecylpyndinium-4-aldoxime bromide. For 0.1 M total surfactant first-order rate constants of hydrolyses of 2,4-dinitrophenyl acetate and octanoate (DNPA and DNPO, respectively) and benzoic anhydride (Bz(2)O) go through maxima at a mole fraction of SDOD of ca. 0.5 for DNPA and DNPO and 0.8 for Bz(2)O. These rate maxima are fitted quantitatively in terms of reactions of OH- and dodecanoate ion on the assumption that sulfobetaine micelles increase the nucleophilicity of the carboxylate ion. This rate effect is ascribed to decreased hydration and ion-pairing of the dodecanoate ion in the mixed micelles, on the basis of H-1 NMR spectrometry in mixtures of SDOD and SB3-14. Therefore, incorporation of dodecanoate ion in SB3-n slows reaction by ''dilution'' in the micelle, but this inhibition is offset by activation of the nucleophilic dodecanoate ion.

  DOI：

  10.1021/j100029a030

文献信息

• Nucleophilically Assisted Deacylation in Sodium Dodecanoate and Dodecyl Sulfate Micelles. Quantitative Evidence on Premicellar Complexes
  作者：Dilma M. O. Marconi、Vera L. A. Frescura、Dino Zanette、Faruk Nome、Clifford A. Bunton

  DOI：10.1021/j100098a042

  日期：1994.11

  Hydrolyses of 2,4-dinitrophenyl acetate and octanoate (DNPA and DNPO, respectively) and benzoic anhydride (Bz(2)O) in the pH range 8.9-10.2 are inhibited by anionic micelles of sodium dodecyl sulfate (SDS), and reactions of fully micellar-bound substrates are very slow. The effect of micellized sodium dodecanoate, SDOD, depends on pH. At high pH reactions of DNPA and Bz(2)O involve OH- and are inhibited by SDOD, but there are significant rates at high [SDOD]. At low-pH reactions of DNPA and Bz(2)O are inhibited at low [SDOD] and assisted at high [SDOD]. The inhibition is due to formation of kinetically ineffective premicellar complexes and rate-surfactant profiles can be fitted quantitatively in terms of this. model. When the substrates are fully micellar-bound rate constants in mixtures of SDOD and SDS follow the mole fraction of SDOD and second-order rate constants of nucleophilic attack by the dodecanoate ion at micellar surfaces are similar to those for the reactions of OAc- in water.
• Effects of Sulfobetaine-Sodium Dodecanoate Micelles on Deacylation and Indicator Equilibrium
  作者：Vera L. A. Frescura、Dilma M. O. Marconi、Dino Zanette、Faruk Nome、Andrei Blasko、Clifford A. Bunton

  DOI：10.1021/j100029a030

  日期：1995.7

  Fractional micellar ionization, ct, and critical micelle concentrations have been measured for mixed micelles of sodium dodecanoate (SDOD) and sulfobetaines (C(n)H(2n+1)N(+)Me(2)(CH2)(3)SO3-, SB3-n, n = 10, 12, 14, 16), and values of pH(app) have been calculated from deprotonation of 1-dodecylpyndinium-4-aldoxime bromide. For 0.1 M total surfactant first-order rate constants of hydrolyses of 2,4-dinitrophenyl acetate and octanoate (DNPA and DNPO, respectively) and benzoic anhydride (Bz(2)O) go through maxima at a mole fraction of SDOD of ca. 0.5 for DNPA and DNPO and 0.8 for Bz(2)O. These rate maxima are fitted quantitatively in terms of reactions of OH- and dodecanoate ion on the assumption that sulfobetaine micelles increase the nucleophilicity of the carboxylate ion. This rate effect is ascribed to decreased hydration and ion-pairing of the dodecanoate ion in the mixed micelles, on the basis of H-1 NMR spectrometry in mixtures of SDOD and SB3-14. Therefore, incorporation of dodecanoate ion in SB3-n slows reaction by ''dilution'' in the micelle, but this inhibition is offset by activation of the nucleophilic dodecanoate ion.