Adriana Esparza-Ruiz, Adrián Peña-Hueso, Julio Hernández-Díaz
Sep 12, 2007
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0
Influential Citations
24
Citations
Journal
Crystal Growth & Design
Abstract
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 → 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 inte...