ortho-fluorophenyl 1,2,3,5-dithiadiazolyl cation | 757924-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ortho-fluorophenyl 1,2,3,5-dithiadiazolyl cation
• CAS: 757924-20-2
• 化学式: C₇H₄FN₂S₂
• 分子量: 199.253
• InChiKey: UZTGOEMXFMNUBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ortho-fluorophenyl 1,2,3,5-dithiadiazolyl cation 在 Zn(Cu) redox couple 作用下， 以 四氢呋喃 为溶剂， 生成 ortho-fluorophenyl 1,2,3,5-dithiadiazolyl
  参考文献：
  名称：

  Solid-state effects of monofluorophenyl substitution in dithiadiazolyl radicals: Impact on S···S and S···N interactions and their classification via Hirshfeld surfaces and fingerprint plots

  摘要：

  Ortho- and para-fluorophenyl 1,2,3,5-dithiadiazolyl (DTDA) radicals were synthesised and structurally characterised in the solid-state. This enables the well-known molecular origins of the electrical conductivity properties in this series of molecules to be studied, specifically S center dot center dot center dot S conduction pathways.This work includes the first report of monofluorophenyl DTDA crystal structures, filling an important gap in the literature to complement the many structural records of di-, tri-, tetra- and pentafluorophenyl DTDA analogues. This report also overturns previous thinking that monofluoro-substitution in these phenyl DTDA compounds does not influence the supramolecular chemistry; indeed, we demonstrate that singular fluorine is indeed structurally (and therefore property) directing as per their di-, tri-, tetra- and pentafluorinated relatives. In particular, the S center dot center dot center dot S and S center dot center dot center dot N interactions that control the electrical conductivity in DTDAs are distinct in these mono-fluorophenyl DTDAs.Hirshfeld surfaces were employed to clarify the nature and extent of these interactions. Their ability to exploit the very sensitive features of surface topologies in order to identify S center dot center dot center dot S and S center dot center dot center dot N intermolecular interactions is important since these interactions are much more subtle than, say, classical hydrogen-bonding.Furthermore, we demonstrate that Hirshfeld surfaces can classify the entire set of intermolecular interactions for a compound via a fingerprint plot. This affords the instant recognition of a given type of DTDA supramolecular network. In turn, barcodes can be generated from these fingerprint plots which quantify the percentage contribution of atom pairs that are involved in intermolecular interactions within DTDAs. The predictive potential of such classification within the field of molecular design is shown via a comparison of our fingerprint plots with those of DTDAs from previous studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.07.066
• 作为产物：
  描述：

  2-氟苯腈 在 lithium hexamethyldisilazane 、 二氯化硫 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 ortho-fluorophenyl 1,2,3,5-dithiadiazolyl cation
  参考文献：
  名称：

  Solid-state effects of monofluorophenyl substitution in dithiadiazolyl radicals: Impact on S···S and S···N interactions and their classification via Hirshfeld surfaces and fingerprint plots

  摘要：

  Ortho- and para-fluorophenyl 1,2,3,5-dithiadiazolyl (DTDA) radicals were synthesised and structurally characterised in the solid-state. This enables the well-known molecular origins of the electrical conductivity properties in this series of molecules to be studied, specifically S center dot center dot center dot S conduction pathways.This work includes the first report of monofluorophenyl DTDA crystal structures, filling an important gap in the literature to complement the many structural records of di-, tri-, tetra- and pentafluorophenyl DTDA analogues. This report also overturns previous thinking that monofluoro-substitution in these phenyl DTDA compounds does not influence the supramolecular chemistry; indeed, we demonstrate that singular fluorine is indeed structurally (and therefore property) directing as per their di-, tri-, tetra- and pentafluorinated relatives. In particular, the S center dot center dot center dot S and S center dot center dot center dot N interactions that control the electrical conductivity in DTDAs are distinct in these mono-fluorophenyl DTDAs.Hirshfeld surfaces were employed to clarify the nature and extent of these interactions. Their ability to exploit the very sensitive features of surface topologies in order to identify S center dot center dot center dot S and S center dot center dot center dot N intermolecular interactions is important since these interactions are much more subtle than, say, classical hydrogen-bonding.Furthermore, we demonstrate that Hirshfeld surfaces can classify the entire set of intermolecular interactions for a compound via a fingerprint plot. This affords the instant recognition of a given type of DTDA supramolecular network. In turn, barcodes can be generated from these fingerprint plots which quantify the percentage contribution of atom pairs that are involved in intermolecular interactions within DTDAs. The predictive potential of such classification within the field of molecular design is shown via a comparison of our fingerprint plots with those of DTDAs from previous studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.07.066