2,2'-二硫代比吡嗪:关于二硫键。

IF 0.7 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Acta Crystallographica Section C Structural Chemistry Pub Date : 2023-09-01 DOI:10.1107/S2053229623007416

Kinga Wzgarda-Raj, Justyna Dominikowska, Natallia Husik, Agnieszka J Rybarczyk-Pirek

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引用次数: 0

摘要

x射线衍射研究表明，吡嗪-2-硫醇在空气条件下缩合成2,2'-二硫代比吡嗪[系统名称:2-(吡嗪-2-基二磺胺基)吡嗪]，C8H6N4S2 (I)。在分子I中，吡嗪环几乎垂直排列，其C-S-S-C扭转角绝对值为-91.45(6)°。在剑桥结构数据库的搜索证实，这种构象是典型的二硫化合物。用量子理论研究了三种不同的二硫化物旋转体。在氢键、硫键和层积相互作用稳定的结构中，观察到能量最低的旋转体处于结晶状态。进一步的量子化学计算证实，2,2′-二硫代比吡嗪可以根据SN2机制反应。

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2,2'-Dithiobispyrazine: about the disulfide bond.

X-ray diffraction studies reveal that pyrazine-2-thiol undergoes condensation to 2,2'-dithiobispyrazine [systematic name: 2-(pyrazin-2-yldisulfanyl)pyrazine], C8H6N4S2 (I), under aerial conditions. In the molecule of I, the pyrazine rings are arranged in an almost perpendicular manner, with an absolute value of the C-S-S-C torsion angle of -91.45 (6)°. A search in the Cambridge Structural Database confirmed that such a conformation is typical for disulfide compounds. Three different rotamers of disulfide I were studied using quantum theoretical studies. The rotamer of lowest energy was observed in the crystalline state in the structure stabilized by hydrogen-bond, chalcogen-bond and stacking interactions. Further quantum chemical computations confirm that 2,2'-dithiobispyrazine can react according to the SN2 mechanism.

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来源期刊

Acta Crystallographica Section C Structural Chemistry CHEMISTRY, MULTIDISCIPLINARYCRYSTALLOGRAPH-CRYSTALLOGRAPHY

CiteScore

1.60

自引率

12.50%

发文量

148

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.