A facile route to C2 substituted imidazolium ionic liquids

ORGN 400

Elliot G. Ennis, ege2a@mtsu.edu and Scott T Handy, shandy@mtsu.edu. Department of Chemistry, Middle Tennessee State University, PO Box 68, Murfreesboro, TN 37132
The imidazolium cation has been the focus of much attention in recent years, most notably as a source of N-heterocyclic carbenes, which can be used either as ligands for transition metal catalysts or as catalysts themselves, and as the cationic component of the most popular family of room temperature ionic liquids. Particularly in this later role, the relative acidity of the C2 position of the imidazolium cation can be either advantageous or disadvantageous depending upon the circumstances. In an effort to prepare new room temperature ionic liquids that will avoid any acid/base chemistry at the C2 position, we have explored the direct alkylation of the C2 position of unsubstituted imidazolium cations as a versatile and concise route to substituted compounds. Details regarding the preparation, properties (melting points and viscosity), and potential applications of these materials will be presented.