Abstract
ABSTRACT In recent studies, n→π* interactions featuring nucleophilic pyridine have been investigated using Fourier transform microwave spectroscopy and high-level theoretical computations. Examples of n→π* of this type in the solid state, however, are limited. The norbornene-based 2-pyridyl imide 1 is a compound that can adopt two conformers, in which the pyridyl nitrogen is either syn or anti to the norbornane bridge. It would be expected that the syn conformation of imide 1 would be more favourable, as indicated in a previous computational study. Here, tandem crystallographic and additional computational studies provide evidence that the otherwise unfavourable anti conformer of imide 1 becomes favoured upon stabilisation by an n→π* interaction in the solid state.
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