An electrostatic gauche effect in β-fluoro and β-hydroxy N-ethylpyridinium cations

Natalie E. J. Gooseman, David O'Hagan, Michael J. G. Peach, Alexandra M. Z. Slawin, David J. Tozer, Robert J. Young,
Angew. Chem. Int. Ed., 46, 5904–5908, 2007.


In my first collaboration with Prof David O’Hagan of the University of St. Andrews, we investigated the gauche effect in a series of organic molecules, attributing it to a series of non-H bonded electrostatic interactions.

For the abstract, and access to the full text, see below.


Left-leaning molecules: As shown by X-ray crystallography, NMR spectroscopy, and DFT calculations, N-(2-fluoroethyl)pyridinium and related cations prefer a gauche conformation. In these systems, the gauche effect is attributed to an electrostatic interaction that does not involve hydrogen bonding.

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