1,2-bis(3-hydrazinylquinoxalin-2-yl)hydrazine | 1010396-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,2-bis(3-hydrazinylquinoxalin-2-yl)hydrazine
• CAS: 1010396-42-5
• 化学式: C₁₆H₁₆N₁₀
• 分子量: 348.37
• InChiKey: ZAOGKPXIXDVCLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  152
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-bis(3-hydrazinylquinoxalin-2-yl)hydrazine 、 1-萘甲醛 以 甲醇 为溶剂， 反应 48.0h， 以95%的产率得到N-[(E)-naphthalen-1-ylmethylideneamino]-3-[2-[3-[(2E)-2-(naphthalen-1-ylmethylidene)hydrazinyl]quinoxalin-2-yl]hydrazinyl]quinoxalin-2-amine
  参考文献：
  名称：

  New Chromogenic and Fluorescent Probes for Anion Detection:  Formation of a [2 + 2] Supramolecular Complex on Addition of Fluoride with Positive Homotropic Cooperativity

  摘要：

  [GRAPHICS]Two new chromogenic and fluorescent probes for anions have been designed, synthesized, and characterized. These probes contain multiple hydrogen bonding donors including hydrazine, hydrazone, and hydroxyl functional groups for potential anion interacting sites. Despite the possible flexible structural framework due to the presence of sp(3) carbon linkage, X-ray structure analysis of probe 2 displayed an essentially planar conformation in the solid state owing to strong crystal packing interactions comprising a combination of favorable pi-pi stacking effect and hydrogen bonding to cocrystallized CH3OH molecules. Both probes I and 2 display orange color in DMSO solution and show fairly weak fluorescence at room temperature. Binding studies revealed that both probes 1 and 2 show noticeable colorimetric and fluorescent responses only to F-, OAc-, and H2PO4- among the nine anions tested (F-, Cl-, Br-, I-, OAc-, H2PO4-, HSO4-, ClO4-, and NO3-). The general trend of the sensitivity to anions follows the order of F- > OAc- > H2PO4- > Cl- > Br- approximate to I- approximate to HSO4- approximate to ClO4- approximate to NO3-. A 1:2 (probe to anion) binding stoichiometry was found for probe 1 with OAc- and H2PO4- and probe 2 with F-, OAc-, and H2PO4-. The binding isotherm of probe 1 to F- was found to be complicated with apparent multiple equilibria occurring in solution. The formation of an aggregated supramolecular complex upon addition of fluoride is proposed to rationalize the observed optical responses and is supported by ESI mass spectrometry and pulsed-field gradient NMR spectroscopy. Data analysis suggests that the binding of probe 1 to F- shows positive homotropic cooperativity.

  DOI：

  10.1021/jo7019916
• 作为产物：
  描述：

  2,3-二氯喹喔啉 在 一水合肼 作用下， 反应 120.0h， 以90%的产率得到1,2-bis(3-hydrazinylquinoxalin-2-yl)hydrazine
  参考文献：
  名称：

  New Chromogenic and Fluorescent Probes for Anion Detection:  Formation of a [2 + 2] Supramolecular Complex on Addition of Fluoride with Positive Homotropic Cooperativity

  摘要：

  [GRAPHICS]Two new chromogenic and fluorescent probes for anions have been designed, synthesized, and characterized. These probes contain multiple hydrogen bonding donors including hydrazine, hydrazone, and hydroxyl functional groups for potential anion interacting sites. Despite the possible flexible structural framework due to the presence of sp(3) carbon linkage, X-ray structure analysis of probe 2 displayed an essentially planar conformation in the solid state owing to strong crystal packing interactions comprising a combination of favorable pi-pi stacking effect and hydrogen bonding to cocrystallized CH3OH molecules. Both probes I and 2 display orange color in DMSO solution and show fairly weak fluorescence at room temperature. Binding studies revealed that both probes 1 and 2 show noticeable colorimetric and fluorescent responses only to F-, OAc-, and H2PO4- among the nine anions tested (F-, Cl-, Br-, I-, OAc-, H2PO4-, HSO4-, ClO4-, and NO3-). The general trend of the sensitivity to anions follows the order of F- > OAc- > H2PO4- > Cl- > Br- approximate to I- approximate to HSO4- approximate to ClO4- approximate to NO3-. A 1:2 (probe to anion) binding stoichiometry was found for probe 1 with OAc- and H2PO4- and probe 2 with F-, OAc-, and H2PO4-. The binding isotherm of probe 1 to F- was found to be complicated with apparent multiple equilibria occurring in solution. The formation of an aggregated supramolecular complex upon addition of fluoride is proposed to rationalize the observed optical responses and is supported by ESI mass spectrometry and pulsed-field gradient NMR spectroscopy. Data analysis suggests that the binding of probe 1 to F- shows positive homotropic cooperativity.

  DOI：

  10.1021/jo7019916

文献信息

• New Chromogenic and Fluorescent Probes for Anion Detection:  Formation of a [2 + 2] Supramolecular Complex on Addition of Fluoride with Positive Homotropic Cooperativity
  作者：Chan-Yu Chen、Tzu-Pin Lin、Chine-Kun Chen、Su-Ching Lin、Mei-Chun Tseng、Yuh-Sheng Wen、Shih-Sheng Sun

  DOI：10.1021/jo7019916

  日期：2008.2.1

  [GRAPHICS]Two new chromogenic and fluorescent probes for anions have been designed, synthesized, and characterized. These probes contain multiple hydrogen bonding donors including hydrazine, hydrazone, and hydroxyl functional groups for potential anion interacting sites. Despite the possible flexible structural framework due to the presence of sp(3) carbon linkage, X-ray structure analysis of probe 2 displayed an essentially planar conformation in the solid state owing to strong crystal packing interactions comprising a combination of favorable pi-pi stacking effect and hydrogen bonding to cocrystallized CH3OH molecules. Both probes I and 2 display orange color in DMSO solution and show fairly weak fluorescence at room temperature. Binding studies revealed that both probes 1 and 2 show noticeable colorimetric and fluorescent responses only to F-, OAc-, and H2PO4- among the nine anions tested (F-, Cl-, Br-, I-, OAc-, H2PO4-, HSO4-, ClO4-, and NO3-). The general trend of the sensitivity to anions follows the order of F- > OAc- > H2PO4- > Cl- > Br- approximate to I- approximate to HSO4- approximate to ClO4- approximate to NO3-. A 1:2 (probe to anion) binding stoichiometry was found for probe 1 with OAc- and H2PO4- and probe 2 with F-, OAc-, and H2PO4-. The binding isotherm of probe 1 to F- was found to be complicated with apparent multiple equilibria occurring in solution. The formation of an aggregated supramolecular complex upon addition of fluoride is proposed to rationalize the observed optical responses and is supported by ESI mass spectrometry and pulsed-field gradient NMR spectroscopy. Data analysis suggests that the binding of probe 1 to F- shows positive homotropic cooperativity.