2,6-diaminopyridine-3,5-bis(selenocyanate) | 1033551-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-diaminopyridine-3,5-bis(selenocyanate)
• 英文别名: 2,6-diaminopyridine-bis(selenocyanate)
• CAS: 1033551-19-7
• 化学式: C₇H₅N₅Se₂
• 分子量: 317.07
• InChiKey: RKXHPRALBOLUFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.13
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112.51
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,6-diaminopyridine-3,5-bis(selenocyanate) 在 gallium(III) trichloride 、 sodium tetrahydroborate 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 17.83h， 生成 4H-bis[1,2,3]selenathiazolo[4,5-b:5',4'-e]pyridin-2-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Resonance Stabilized Bisdiselenazolyls as Neutral Radical Conductors

  摘要：

  An efficient and versatile synthetic route to resonance stabilized bisselenathiazolyl and bisdiselenazolyl radicals 3 and 4 is described. Structural analysis of 3 and 4 confirm that lattice and pi-delocalization energies are sufficient to offset solid-state dimerization of the radicals and that the two selenium-containing radicals are isostructural with the all-sulfur based system 1. Variable temperature conductivity measurements indicate that sequential replacement of sulfur by selenium leads to a progressive increase in conductivity and reduction in thermal activation energy.

  DOI：

  10.1021/ja0666856
• 作为产物：
  描述：

  2,6-二氨基吡啶 、 potassium selenocyanate 在 溴 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以71%的产率得到2,6-diaminopyridine-3,5-bis(selenocyanate)
  参考文献：
  名称：

  Resonance Stabilized Bisdiselenazolyls as Neutral Radical Conductors

  摘要：

  An efficient and versatile synthetic route to resonance stabilized bisselenathiazolyl and bisdiselenazolyl radicals 3 and 4 is described. Structural analysis of 3 and 4 confirm that lattice and pi-delocalization energies are sufficient to offset solid-state dimerization of the radicals and that the two selenium-containing radicals are isostructural with the all-sulfur based system 1. Variable temperature conductivity measurements indicate that sequential replacement of sulfur by selenium leads to a progressive increase in conductivity and reduction in thermal activation energy.

  DOI：

  10.1021/ja0666856

文献信息

• Enhanced Conductivity and Magnetic Ordering in Isostructural Heavy Atom Radicals
  作者：Craig M. Robertson、Alicea A. Leitch、Kristina Cvrkalj、Robert W. Reed、Daniel J. T. Myles、Paul A. Dube、Richard T. Oakley

  DOI：10.1021/ja801070d

  日期：2008.7.1

  Synthetic methods have been developed to generate the complete series of resonance-stabilized heterocyclic thia/selenazyl radicals 1a-4a. X-ray crystallographic studies confirm that all four radicals are isostructural, belonging to the tetragonal space group P (4) over bar2(1)m. The crystal structures consist of slipped pi-stack arrays of undimerized radicals packed about (4) over bar centers running along the z direction, an arrangement which gives rise to a complex lattice-wide network of close intermolecular E-2-E-2' contacts. Variable temperature conductivity (sigma) measurements reveal an increase in conductivity with increasing selenium content, particularly so When selenium occupies the E-2 position, with sigma(300 K) reaching a maximum (for E-1 = E-2 = Se) of 3.0 x 10(-4) S cm(-1). Thermal activation energies E-act follow a similar profile, decreasing with increasing selenium content along the series 1a (0.43 eV), 3a (0.31 eV), 2a (0.27 eV), 4a (0.19 eV). Variable temperature magnetic susceptibility measurements indicate that all four radicals exhibit S = 1/2 Curie-Weiss behavior over the temperature range 20-300 K. At lower temperatures, the three selenium-based radicals display magnetic ordering. Radical 3a, with selenium positioned at the E-1 site, undergoes a phase transition at 14 K to a weakly spin-canted (phi = 0.010 degrees) antiferromagnetic state. By contrast, radicals 2a and 4a, which both possess selenium in the E-2 position, order ferromagnetically, with Curie temperatures of T-c = 12.8 and 17.0 K, respectively. The coercive fields H-c at 2 K of 2a (250 Oe) and 4a (1370 Oe) are much larger than those seen in conventional light atom organic ferromagnets. The transport properties of the entire series 1a-4a are discussed in the light of Extended Huckel Theory band structure calculations.