4-(2-fluoroethyl)-1-phenyl-4H-1,2,4-triazol-1-ium triflate | 1442434-03-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4-(2-fluoroethyl)-1-phenyl-4H-1,2,4-triazol-1-ium triflate
• CAS: 1442434-03-8
• 化学式: CF₃O₃S*C₁₀H₁₁FN₃
• 分子量: 341.286
• InChiKey: UPHJBRLXUSMSCC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(2-fluoroethyl)-1-phenyl-4H-1,2,4-triazol-1-ium triflate 、 silver(l) oxide 在 四甲基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以58%的产率得到bis(4-(2-fluoroethyl)-1-phenyl-1H-1,2,4-triazol-5(4H)-ylidene)silver(I) triflate
  参考文献：
  名称：

  The fluorine-NHC gauche effect: a structural and computational study

  摘要：

  Herein, we report the synthesis and X-ray structural analysis of a collection of fluorinated metal N-heterocyclic carbenes (Ag, Au, Pd, Rh, Ir) and their precursor salts. The common structural feature of these species is a flanking fluoroethyl group, which is either freely rotating or embedded within a bicyclic framework. Solid state analysis confirmed a gauche conformational preference in all cases with the fluorine adopting a syn clinal arrangement (phi([NCCF])similar to 60 degrees) with respect to the triazolium nitrogen at the vicinal position of the NHC. A density functional theory analysis was employed to quantify these effects and evaluate the influence of electronic modulation of the carbenic carbon [(C=N+); neutral carbene (C:); metal-bound carbene (C=M)], on the relative gauche/anti preference, thus highlighting the potential of this conformational phenomenon as a useful molecular design strategy for controlling the topology of organometallic complexes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.071
• 作为产物：
  描述：

  碘苯 在 copper(I) oxide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 112.0h， 生成 4-(2-fluoroethyl)-1-phenyl-4H-1,2,4-triazol-1-ium triflate
  参考文献：
  名称：

  The fluorine-NHC gauche effect: a structural and computational study

  摘要：

  Herein, we report the synthesis and X-ray structural analysis of a collection of fluorinated metal N-heterocyclic carbenes (Ag, Au, Pd, Rh, Ir) and their precursor salts. The common structural feature of these species is a flanking fluoroethyl group, which is either freely rotating or embedded within a bicyclic framework. Solid state analysis confirmed a gauche conformational preference in all cases with the fluorine adopting a syn clinal arrangement (phi([NCCF])similar to 60 degrees) with respect to the triazolium nitrogen at the vicinal position of the NHC. A density functional theory analysis was employed to quantify these effects and evaluate the influence of electronic modulation of the carbenic carbon [(C=N+); neutral carbene (C:); metal-bound carbene (C=M)], on the relative gauche/anti preference, thus highlighting the potential of this conformational phenomenon as a useful molecular design strategy for controlling the topology of organometallic complexes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.071