Intermolecular interactions in bromo-, methyl-, and cyanoimidazole derivatives

Materials containing bistable N-H�N hydrogen bonds, such as imidazole crystals, show promise for applications in electronics. Herein, we examine the effect of imidazole functionalization upon structural parameters relating to proton transfer, molecular rotation, and order-disorder transitions. Three different substituents are studied: methyl-, bromo-, and cyano-, resulting in steric, electronic, and supramolecular modification of the imidazole core. © 2013 American Chemical Society