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], C 8 H 6 N 4 S 2 ( I ), under aerial conditions. In the molecule of I , the pyrazine rings are arranged in an almost perpendicular manner, wit...

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Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2023-09, Vol.79 (9), p.374-380
Main Authors: Wzgarda-Raj, Kinga, Dominikowska, Justyna, Husik, Natallia, Rybarczyk-Pirek, Agnieszka J.
Format: Article
Language:English
Subjects:
Quantum chemistry
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Summary:X-ray diffraction studies reveal that pyrazine-2-thiol undergoes condensation to 2,2′-dithiobispyrazine [systematic name: 2-(pyrazin-2-yldisulfanyl)pyrazine], C 8 H 6 N 4 S 2 ( 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 S N 2 mechanism.
ISSN:2053-2296
0108-2701
2053-2296
1600-5759
DOI:10.1107/S2053229623007416