2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-ium triflate | 1385789-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-ium triflate
• 英文别名: 2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-iumtriflate
• CAS: 1385789-82-1
• 化学式: CF₃O₃S*C₃₂H₃₃BNS
• 分子量: 623.568
• InChiKey: GVGYSOLSPNMEAT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  43.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-ium triflate 在 四丁基氟化铵 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以84%的产率得到dimesityl (4-(3-methylbenzo[d]thiazol-3-ium-2-yl)phenyl)fluoroborate
  参考文献：
  名称：

  Turn-on colorimetric sensing of fluoride ions by a cationic triarylborane bearing benzothiazolium

  摘要：

  A cationic triarylborane Lewis acid bearing benzothiazolium moiety, 2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-ium ([2](+)) was prepared from a neutral borane (2a) and their crystal structures were determined from X-ray diffraction studies. While 2a shows a blue-shift with a small decrease in the UV-vis absorption band upon fluoride binding to the boron atom, [2](+) undergoes a red-shift of the absorption band which tails over visible region, giving rise to the color change of the solution from colorless to yellow. The fluoride binding constant in THF/H2O (9/1, v/v) is calculated to be 1.3 x 10(4) M-1 that is much greater than that of a neutral borane 2a (K = 4.2 x 10(2) M-1). DFT calculation results suggest that the absorption process in the fluoroborate (2F) is involved with pi(Mes)->pi*(phenylbenzothiazolium) intramolecular charge transfer and the greater elevation of the pi(Mes) donor level is responsible for the turn-on colorimetric response of [2](+). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.04.020
• 作为产物：
  描述：

  2-(4-溴苯基)苯并噻唑 在 n-BuLi 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-ium triflate
  参考文献：
  名称：

  Turn-on colorimetric sensing of fluoride ions by a cationic triarylborane bearing benzothiazolium

  摘要：

  A cationic triarylborane Lewis acid bearing benzothiazolium moiety, 2-(4'-dimesitylborylphenyl)-3-methylbenzo[d]thiazol-3-ium ([2](+)) was prepared from a neutral borane (2a) and their crystal structures were determined from X-ray diffraction studies. While 2a shows a blue-shift with a small decrease in the UV-vis absorption band upon fluoride binding to the boron atom, [2](+) undergoes a red-shift of the absorption band which tails over visible region, giving rise to the color change of the solution from colorless to yellow. The fluoride binding constant in THF/H2O (9/1, v/v) is calculated to be 1.3 x 10(4) M-1 that is much greater than that of a neutral borane 2a (K = 4.2 x 10(2) M-1). DFT calculation results suggest that the absorption process in the fluoroborate (2F) is involved with pi(Mes)->pi*(phenylbenzothiazolium) intramolecular charge transfer and the greater elevation of the pi(Mes) donor level is responsible for the turn-on colorimetric response of [2](+). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.04.020