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

Reference:

Richter, I., Warren, M. R., Minari, J., Elfeky, S. A., Chen, W., Mahon, M. F., Raithby, P., James, T. D., Sakurai, K., Teat, S. J., Bull, S. D. and Fossey, J. S., 2009. Solid-State Structures and Solution Analyses of a Phenylpropylpyridine N-Oxide and an N-Methyl Phenylpropylpyridine. Chemistry - An Asian Journal, 4 (1), pp. 194-198.

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Official URL:

http://dx.doi.org/10.1002/asia.200800255

Abstract

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 -stacking, as judged by excimer emission and a lack of corresponding cross peaks, respectively.

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