6-perfluoromethylsulfonyl-2-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-perfluoromethylsulfonyl-2-naphthol
• 英文别名: 6-(Trifluoromethylsulfonyl)naphthalen-2-ol；6-(trifluoromethylsulfonyl)naphthalen-2-ol
• 化学式: C₁₁H₇F₃O₃S
• 分子量: 276.236
• InChiKey: HRDJLAPODMOYHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-萘酚-6-磺酸 在 lithium hydroxide 、 sodium hydroxide 、 N,N-二甲基乙酰胺 、 sodium ethanolate 、 间氯过氧苯甲酸 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 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

文献信息

• Photochemistry of “Super” Photoacids. 3. Excited-State Proton Transfer from Perfluoroalkylsulfonyl-Substituted 2-Naphthols
  作者：Caroline Clower、Kyril M. Solntsev、Janusz Kowalik、Laren M. Tolbert、Dan Huppert

  DOI：10.1021/jp012774n

  日期：2002.4.1

  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.