Solid-State Structures and Solution Analyses of a Phenylpropylpyridine N-Oxide and an N-Methyl Phenylpropylpyridine

The crystal structures of phenylpropylpyridine-N-oxide and N-methyl-phenylpropylpyridinium iodide are compared, revealing that hydrogen bonding with the solvent molecule plays an important role in the N-oxide compound, whilst electrostatic interactions are predominant in controlling the solid-state orientation of the N-methylated compound. Fluorescence spectroscopy and NOESY indicate that in contrast to the previously reported pyridinium iodide, the N-oxide is not subject to intramolecular pi-stacking, as judged by excimer emission and a lack of corresponding cross peaks, respectively.