Effect of Weak Sulfur Interactions and Hydrogen Bonds in the Folded or Unfolded Conformation of bis[2-(1H-Benzimidazol-2-yl)phenyl]disulfide Derivatives

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• 作者：Adriana Esparza-Ruiz ; Adriá ; n Pe&ntilde ; a-Hueso ; Julio Herná ; ndez-Dí ; az ; Angelina Flores-Parra ; Rosalinda Contreras
• 刊名：Crystal Growth & Design
• 出版年：2007
• 出版时间：October 2007
• 年：2007
• 卷：7
• 期：10
• 页码：2031 - 2040
• 全文大小：713K
• 年卷期：v.7,no.10(October 2007)
• ISSN：1528-7505

文摘

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-polymorphsof 1 have shown that the conformation of 1 is the result of sulfur weak N S intramolecular interactions, where the sulfur atomis acting as a Lewis acid. Nitrogen protonation changes the elongated conformation of 1 into a folded conformation for 2-4 and asemifolded conformation in compounds 5 and 6 with the assistance of intramolecular - stacking and hydrogen bonds, whichbridge the two halves of the molecules. All disulfides adopt chiral conformations in the solid state; the ensemble of these chiralconformations is racemic. They present polymeric arrays with multiple cooperative stabilizing intermolecular and intramolecularinteractions like -interactions, O S, C() S, N() S, F S, and H-bonds.