Nuran Özçiçek Pekmez,^a,* Muzaffer Can,^b Attila Yildiza

^a Hacettepe University, Department of Chemistry, 06532, Beytepe, Ankara, Turkey.
Fax: +903122992163,
E-mail: npekmez@hacettepe.edu.tr
^b Department of Chemistry, Gaziosmanpasa University, 60250 Tasliciftlik, Tokat, Turkey

Abstract
The electroreductions of imidazole and 2-aminoimidazole were investigated on a Pt electrode in acetonitrile containing tetrabutylammonium tetrafluoroborate with and without the presence of HBF₄. The effects of lithium and tetrabutylammonium ions on the electroreduction and FTIR and 1H NMR results were also compared. The feasibility of the formation of intermolecular hydrogen bonds was elucidated by the use of the theoretical calculations. Electroreduction waves were interpreted by the existence of the hydrogen-bonded clusters in acetonitrile containing tetrabutylammonium tetrafluoroborate.

Keywords: imidazole, 2-aminoimidazole, hydrogen bond, NMR, FTIR, theoretical investigation