2,5-dihydroxybenzyl thioacetate | 171366-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-dihydroxybenzyl thioacetate
• 英文别名: S-[(2,5-dihydroxyphenyl)methyl] ethanethioate
• CAS: 171366-64-6
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: OYWAFGZBXQSEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,5-dihydroxybenzyl thioacetate 在 盐酸 作用下， 反应 5.0h， 以80.9%的产率得到2,5-dihydroxybenzyl mercaptan
  参考文献：
  名称：

  In Situ Fourier Transform Infrared Spectroscopy of Molecular Adsorbates at Electrode-Electrolyte Interfaces: A Comparison between Internal and External Reflection Modes

  摘要：

  The vibrational properties of 2,5-dihydroxybenzyl mercaptan (DHBM) irreversibly adsorbed on gold electrodes have been examined in situ in aqueous 0.1 M HClO4 by two different Fourier transform infrared (FT-IR) spectroscopic techniques: (i) potential difference attenuated total reflection FT-IR (PD-ATR-FT-IR), using a thin layer of gold (similar to 4 nm) sputtered on a (thick layer) Au-patterned ZnSe internal reflection element as the electrode and (ii) PD-FT-IR (external) reflection absorption spectroscopy (PD-FT-IRRAS) on a solid Au electrode. The results obtained with both techniques, using the spectrum of the monolayer in the reduced state as a reference, were found to be nearly identical, displaying a set of negative- and positive-pointing features. The first set matched, within experimental error, the most prominent peaks observed in the ATR-FT-IR spectra of the DHBM monolayer using either pure water or 0.1 M HClO4 as a reference. Furthermore, the positive-pointing features in the PD-FT-IR spectra, which correspond to the product of the electrochemical oxidation of irreversibly adsorbed DHBM, were consistent with the presence of a quinone-type moiety, as would be expected on the basis of chemical considerations. These observations indicate that, to the level of sensitivity of these two methodologies, the mode of adsorption and reactivity of DHBM (and probably a number of other species as well) is not appreciably affected by possible differences in the metal surface microstructure.

  DOI：

  10.1021/ac00120a013
• 作为产物：
  描述：

  2,5-dimethoxybenzyl thioacetate 在 三氯化铝 、 丙烷-1-硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以46.8%的产率得到2,5-dihydroxybenzyl thioacetate
  参考文献：
  名称：

  In Situ Fourier Transform Infrared Spectroscopy of Molecular Adsorbates at Electrode-Electrolyte Interfaces: A Comparison between Internal and External Reflection Modes

  摘要：

  The vibrational properties of 2,5-dihydroxybenzyl mercaptan (DHBM) irreversibly adsorbed on gold electrodes have been examined in situ in aqueous 0.1 M HClO4 by two different Fourier transform infrared (FT-IR) spectroscopic techniques: (i) potential difference attenuated total reflection FT-IR (PD-ATR-FT-IR), using a thin layer of gold (similar to 4 nm) sputtered on a (thick layer) Au-patterned ZnSe internal reflection element as the electrode and (ii) PD-FT-IR (external) reflection absorption spectroscopy (PD-FT-IRRAS) on a solid Au electrode. The results obtained with both techniques, using the spectrum of the monolayer in the reduced state as a reference, were found to be nearly identical, displaying a set of negative- and positive-pointing features. The first set matched, within experimental error, the most prominent peaks observed in the ATR-FT-IR spectra of the DHBM monolayer using either pure water or 0.1 M HClO4 as a reference. Furthermore, the positive-pointing features in the PD-FT-IR spectra, which correspond to the product of the electrochemical oxidation of irreversibly adsorbed DHBM, were consistent with the presence of a quinone-type moiety, as would be expected on the basis of chemical considerations. These observations indicate that, to the level of sensitivity of these two methodologies, the mode of adsorption and reactivity of DHBM (and probably a number of other species as well) is not appreciably affected by possible differences in the metal surface microstructure.

  DOI：

  10.1021/ac00120a013