Name: Pyridine-4-thiol. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Pyridine-4-thiol, is researched, Molecular C5H5NS, CAS is 4556-23-4, about Ionic cocrystals of dithiobispyridines: the role of I···I halogen bonds in the building of iodine frameworks and the stabilization of crystal structures. Author is Wzgarda-Raj, Kinga; Nawrot, Martyna; Rybarczyk-Pirek, Agnieszka J.; Palusiak, Marcin.
It has been confirmed that mercaptopyridines undergo spontaneous condensation in redox reaction with iodine-forming dithiopyridines. In the solid state, these compounds are protonated at the N atoms and cocrystallize with iodine forming salt structures, namely, 2-[(pyridin-2-yl)disulfanyl]pyridinium triiodide sesquiiodine, C10H9N2S2+·I3-·1.5I2, and 4,4′-(disulfanediyl)dipyridinium pentaiodide triiodide, C10H10N2S22+·I5-·I3-. Dithiopyridine cations are packed among three-dimensional frameworks built from iodide anions and neutral iodine mols., and are linked by hydrogen, halogen and chalcogen interactions. Quantum chem. computations indicated that dithiopyridines exhibit anomalously high nitrogen basicity which qualify them as potential proton sponges.
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Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts