Acetic acid 6-trifluoromethylsulfanyl-naphthalen-2-yl ester | 420115-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Acetic acid 6-trifluoromethylsulfanyl-naphthalen-2-yl ester
• CAS: 420115-12-4
• 化学式: C₁₃H₉F₃O₂S
• 分子量: 286.274
• InChiKey: FPXLSWTVNZPDMH-UHFFFAOYSA-N

物化性质

• 沸点：
  308.8±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 6-trifluoromethylsulfanyl-naphthalen-2-yl ester 在 lithium hydroxide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 6-perfluoromethylsulfonyl-2-naphthol
  参考文献：
  名称：

  Photochemistry of “Super” Photoacids. 3. Excited-State Proton Transfer from Perfluoroalkylsulfonyl-Substituted 2-Naphthols

  摘要：

  As a continuation of our efforts in the synthesis and investigation of novel "super" photoacids, in this article we report on the effect of fluoroalkanesulfonyl groups on the photoacidity of 2-naphthol. These groups, known to be the strongest electron-withdrawing substituents, were expected to increase the photoacidity to a greater extent as compared to previously described cyano- and methanesulfonyl groups. Indeed, we have found that 6-perfluoromethylsulfonyl-2-naphthol (6F3) is more acidic in the ground state and noticeably more acidic in the excited state than is previously synthesized 6-cyano-2-naphthol. The unusually short fluorescence lifetimes of the naphthol and the conjugated anion, which are explained by effective resonance/intramolecular charge transfer, mask the extended photoacidity of 6F3. Photochemical investigations of 6-perfluorohexylsulfonyl-2-naphthol(6F13) in protic solvents are complicated by aggregation.

  DOI：

  10.1021/jp012774n
• 作为产物：
  描述：

  6-(Isobutoxycarbonyloxy)naphthalene-2-sulphonyl chloride 在 sodium ethanolate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 Acetic acid 6-trifluoromethylsulfanyl-naphthalen-2-yl ester
  参考文献：
  名称：

  Photochemistry of “Super” Photoacids. 3. Excited-State Proton Transfer from Perfluoroalkylsulfonyl-Substituted 2-Naphthols

  摘要：

  As a continuation of our efforts in the synthesis and investigation of novel "super" photoacids, in this article we report on the effect of fluoroalkanesulfonyl groups on the photoacidity of 2-naphthol. These groups, known to be the strongest electron-withdrawing substituents, were expected to increase the photoacidity to a greater extent as compared to previously described cyano- and methanesulfonyl groups. Indeed, we have found that 6-perfluoromethylsulfonyl-2-naphthol (6F3) is more acidic in the ground state and noticeably more acidic in the excited state than is previously synthesized 6-cyano-2-naphthol. The unusually short fluorescence lifetimes of the naphthol and the conjugated anion, which are explained by effective resonance/intramolecular charge transfer, mask the extended photoacidity of 6F3. Photochemical investigations of 6-perfluorohexylsulfonyl-2-naphthol(6F13) in protic solvents are complicated by aggregation.

  DOI：

  10.1021/jp012774n