2,6-diaminopyridine-3,5-dithiol | 289895-17-6

• 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-dithiol
• 英文别名: 2,6-diamino-3,5-dithiopyridine；2,6-Diaminopyridine-3,5-dithiol
• CAS: 289895-17-6
• 化学式: C₅H₇N₃S₂
• 分子量: 173.263
• InChiKey: LVIOXYDZLDHXDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-diaminopyridine-3,5-dithiol 在 二氯化二硫 作用下， 以 氯苯 为溶剂， 反应 16.0h， 以75%的产率得到8-chloro-4H-bis[1,2,3]dithiazolo[4,5:5'4']pyridin-2-ium chloride
  参考文献：
  名称：

  具有两性离子基态的抗芳香族双 (1,2,3-二噻唑)

  摘要：

  DOI：

  10.1021/ja0016497
• 作为产物：
  描述：

  2,6-二氨基吡啶 在 sodium sulfide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 2,6-diaminopyridine-3,5-dithiol
  参考文献：
  名称：

  Resonance-Stabilized 1,2,3-Dithiazolo-1,2,3-dithiazolyls as Neutral π-Radical Conductors

  摘要：

  Alkylation of the zwitterionic heterocycle 8-chloro-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridine (CIBP) with alkyl triflates affords 8-chloro-4-alkyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridin-2-ium triflates [CIBPR]-[OTf] (R = Me, Et, Pr). Reduction of these salts with decamethylferrocene affords the corresponding CIBPR radicals as thermally stable crystalline solids. The radicals have been characterized in solution by cyclic voltammetry and EPR spectroscopy. Measured electrochemical cell potentials and computed (B3LYP/631 G**) gas-phase disproportionation enthalpies are consistent with a low on-site Coulombic barrier U to charge transfer in the solid state. The crystal structures of CIBPR (R = Me, Et, Pr) have been determined by X-ray crystallography (at 293 K). All three structures consist of slipped pi-stacks of undimerized radicals, with many close intermolecular S...S contacts. CIBPMe undergoes a phase transition at 93 K to a slightly modified slipped g-stack arrangement, the structure of which has also been established crystallographically (at 25 K). Variable-temperature magnetic and conductivity measurements have been performed, and the results interpreted in light of extended Huckel band calculations. The room-temperature conductivities of CIBPR systems (sigma(RT) approximate to 10(-5) to 10(-6) S cm(-1)), as well as the weak 1 D ferromagnetism exhibited by CIBPMe, are interpreted in terms of weak intermolecular overlap along the pi-stacks. The latter is caused by slippage of the molecular plates, a feature necessitated by the steric size of the R and Cl groups on the pyridine ring.

  DOI：

  10.1021/ja026118s

文献信息

• Synthesis, Spectroscopic Characterization and Preliminary Antimicrobial Studies of Mn(II) and Cu(II) Complexes of two Thiolates; S,S’-(2,6-Diaminopyridine-3,5-diyl) Dibenzenecarbothioate (DBCT) and S-Benzyl Benzenecarbothioate (BBCT)
  作者：P. O. Ukoha、C.U. Alioke、N.L> Obasi、K.F. Chah

  DOI：10.1155/2011/214870

  日期：——

  S,S’-(2,6-Diaminopyridine-3,5-diyl)dibenzenecarbothioate was formed by condensing 2,6-diamino-3,5-dithiopyridine and benzoyl chloride in the presence of pyridine. AlsoS-benzyl benzenecarbothioate was prepared by the condensation of benzoyl chloride and phenylmethanethiol in the presence of pyridine. The complexes of these compounds were prepared using copper(II) and manganese(II) chloride salts. The thiolates were characterized on the basis of their electronic, infrared and NMR spectra whereas the complexes were characterized via electronic and infrared studies. The IR spectral studies indicate that the ligands coordinated through the carbonyl oxygen, the sulphur atom and also with the amino group in DBCT. Antimicrobial studies on the ligands and their complexes showed varying degrees of inhibition on the growth of the following microorganisms;Staphylococcus aureus(ATCC 25923),Pseudomonas aeruginosa(ATCC 27853),Bacillus subtilis(ATCC 6633) andCandida albicans(ATCC 2091). The compounds showed no activity againstEscherichia coli(ATCC 25922)

  在吡啶的存在下，2,6-二氨基-3,5-二硫代吡啶和苯甲酰氯缩合生成S,S'-(2,6-二氨基吡啶-3,5-二基)二苯基羧硫酸酯。同时，在吡啶的存在下，苯甲酰氯和苯基甲硫醇缩合生成S-苄基二苯基羧硫酸酯。这些化合物的配合物是使用铜(II)和锰(II)氯化盐制备的。基于电子、红外和NMR光谱，硫醇基团得到了表征，而配合物则通过电子和红外光谱研究进行了表征。红外光谱研究表明，配体通过羰基氧、硫原子以及DBCT的氨基与金属离子配位。对这些配体及其配合物的抗菌研究显示，它们对以下微生物的生长抑制程度不同：金黄色葡萄球菌（ATCC 25923）、铜绿假单胞菌（ATCC 27853）、枯草芽孢杆菌（ATCC 6633）和白色念珠菌（ATCC 2091）。这些化合物对大肠杆菌（ATCC 25922）无活性。
• Antiaromatic Bis(1,2,3-dithiazoles) with Zwitterionic Ground States
  作者：Leanne Beer、Richard T. Oakley、James R. Mingie、Kathryn E. Preuss、Nicholas J. Taylor、A. Wallace Cordes

  DOI：10.1021/ja0016497

  日期：2000.8.1
• Resonance-Stabilized 1,2,3-Dithiazolo-1,2,3-dithiazolyls as Neutral π-Radical Conductors
  作者：Leanne Beer、Jaclyn L. Brusso、A. Wallace Cordes、Robert C. Haddon、Mikhail E. Itkis、Kristin Kirschbaum、Douglas S. MacGregor、Richard T. Oakley、A. Alan Pinkerton、Robert W. Reed

  DOI：10.1021/ja026118s

  日期：2002.8.1

  Alkylation of the zwitterionic heterocycle 8-chloro-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridine (CIBP) with alkyl triflates affords 8-chloro-4-alkyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridin-2-ium triflates [CIBPR]-[OTf] (R = Me, Et, Pr). Reduction of these salts with decamethylferrocene affords the corresponding CIBPR radicals as thermally stable crystalline solids. The radicals have been characterized in solution by cyclic voltammetry and EPR spectroscopy. Measured electrochemical cell potentials and computed (B3LYP/631 G**) gas-phase disproportionation enthalpies are consistent with a low on-site Coulombic barrier U to charge transfer in the solid state. The crystal structures of CIBPR (R = Me, Et, Pr) have been determined by X-ray crystallography (at 293 K). All three structures consist of slipped pi-stacks of undimerized radicals, with many close intermolecular S...S contacts. CIBPMe undergoes a phase transition at 93 K to a slightly modified slipped g-stack arrangement, the structure of which has also been established crystallographically (at 25 K). Variable-temperature magnetic and conductivity measurements have been performed, and the results interpreted in light of extended Huckel band calculations. The room-temperature conductivities of CIBPR systems (sigma(RT) approximate to 10(-5) to 10(-6) S cm(-1)), as well as the weak 1 D ferromagnetism exhibited by CIBPMe, are interpreted in terms of weak intermolecular overlap along the pi-stacks. The latter is caused by slippage of the molecular plates, a feature necessitated by the steric size of the R and Cl groups on the pyridine ring.