Synthesis and crystal structures of 2-bromo-1,3-dimethylimidazolium iodides Article Swipe

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Methyl iodide Adduct Halogenation Iodide Chemistry Crystal structure Medicinal chemistry Hydrogen bond Methane Imidazole Stereochemistry Organic chemistry Molecule

Martin Lampl , Gerhard Laus , Volker Kahlenberg , Klaus Wurst , Hubert Huppertz , Herwig Schottenberger ·

YOU? · · 2018 · Open Access · · DOI: https://doi.org/10.1107/s2056989018003390 · OA: W2791772077

Attempts at direct bromination of 1,3-dimethylimidazolium salts were futile. The title compounds, 2-bromo-1,3-dimethylimidazolium iodide chloroform 0.33-solvate, C 5 H 8 BrN 2 + ·I − ·0.33CHCl 3 , 2-bromo-1,3-dimethylimidazolium iodide dichloromethane hemisolvate, C 5 H 8 BrN 2 + ·I − ·0.5CH 2 Cl 2 , and 2-bromo-1,3-dimethylimidazolium iodide hemi(diiodide), C 5 H 8 BrN 2 + ·I − ·0.5I 2 , were obtained by methylation of 2-bromo-1-methylimidazole. They crystallized as CHCl 3 , CH 2 Cl 2 or I 2 solvates/adducts. The Br atom acts as a σ-hole to accept short C—Br...I interactions. C—H...I hydrogen bonds are observed in each structure.