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Synthesis and X-Ray Crystal Structure of Fluorous Imidazolium Salts

A. Moghimi^a,*, H.R. Khavassi^b, A.H. Benvidi^c, M. Vojdani^c and N. Faghihimoghaddam^c

^aDepartment of Chemistry, Imam Hossein University, Tehran, Iran, P.O. Box 16575-347
^bDepartment of Chemistry, Shahid Beheshti University, Tehran, Iran
^cDepartment of Chemistry, Islamic Azad University, North Branch, Tehran, Iran

      Synthesis of two salts involving CH₂O spacer between the imidazole nitrogen and hexafluoroisopropyl group in the fluorous imidazolium cations is reported. Such an insertion would result in the formation of a-ammonium ether. The two fluorous imidazolium salts involve one or two -CH₂OCH(CF₃)₂ groups attached to the imidazole nitrogen atoms. These products were synthesized from the reaction between methyimidazole and imidazole as nucleophiles and sevochlorane, ClCH₂OCH(CF₃)₂, as electrophile, in different molar ratios. The resulting products have been characterized by ¹H, ¹³C, and ¹⁹F NMR and FTIR spectroscopy. Also, the single crystal X-ray diffraction analysis for the symmetrically substituted imidazolium product is presented. The preliminary animal tests indicated no anesthetic property but the two tested salts were found to behave as calmative.

Keywords: Imidazole, Imidazolium, Fluorous, -Ammonium ether, X-Ray crystal structure