Solid‐State Structures and Solution Analyses of a Phenylpropylpyridine N‐Oxide and an N‐Methyl Phenylpropylpyridine |
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| Authors: | Isabella Richter Mark R Warren Jusaku Minari Souad A Elfeky Wenbo Chen Mary F Mahon Paul R Raithby Prof Tony D James Kazuo Sakurai Simon J Teat Steven D Bull John S Fossey Dr |
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| Institution: | 1. Department of Chemistry, The University of Bath, Claverton Down, Bath, BA2 7AY (UK), Fax: (+44)?122?538?62?31;2. Current Address: Faculty of Environmental Engineering, Department of Chemical Process and Environments, The University of Kitakyushu, 1‐1, Hibikino, Wakamatsu‐ku, Kitakyushu, Fukuoka, (Japan);3. Advanced Light Source, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA);4. New Address: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT (UK) |
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| 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 π‐stacking, as judged by excimer emission and a lack of corresponding cross peaks, respectively. |
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| Keywords: | cations fluorescence hydrogen bonds alkylpyridines π ‐stacking |
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