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Solid‐State Structures and Solution Analyses of a Phenylpropylpyridine N ‐Oxide and an N ‐Methyl Phenylpropylpyridine
Author(s) -
Richter Isabella,
Warren Mark R.,
Minari Jusaku,
Elfeky Souad A.,
Chen Wenbo,
Mahon Mary F.,
Raithby Paul R.,
James Tony D.,
Sakurai Kazuo,
Teat Simon J.,
Bull Steven D.,
Fossey John S.
Publication year - 2009
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800255
Subject(s) - intramolecular force , iodide , hydrogen bond , oxide , pyridinium , molecule , chemistry , crystallography , stacking , solvent , crystal structure , solid state , fluorescence , methyl iodide , photochemistry , stereochemistry , inorganic chemistry , medicinal chemistry , organic chemistry , physics , optics
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.