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 π-stacking, as judged by excimer emission and a lack of corresponding cross peaks, respectively. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.