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Syntheses and structural study of the new compounds bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide (1) and bis[2-(3H-benzimidazol-1-ium-2-yl)-phenyl]disulfide sulfate (2), and their corresponding bis-hydrogen sulfate (3), bis-dihydrogen-phosphate (4), bis-tetrafluoroborate (5) and bis-perchlorate (6), are reported. X-ray diffraction analyses of 2-6 and three pseudo-polymorphs of 1 have shown that the conformation of 1 is the result of sulfur weak N f S intramolecular interactions, where the sulfur atom is acting as a Lewis acid. Nitrogen protonation changes the elongated conformation of 1 into a folded conformation for 2-4 and a semifolded conformation in compounds 5 and 6 with the assistance of intramolecular π-π stacking and hydrogen bonds, which bridge the two halves of the molecules. All disulfides adopt chiral conformations in the solid state; the ensemble of these chiral conformations is racemic. They present polymeric arrays with multiple cooperative stabilizing intermolecular and intramolecular interactions like π-interactions, O f S, C(π) f S, N(π) f S, F f S, and H-bonds.

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