795309-01-2Relevant academic research and scientific papers
Orientation and alkylation effects on cation-π interactions in aqueous solution
Rashkin, Mark J.,Hughes, Robert M.,Calloway, Nathaniel T.,Waters, Marcey L.
, p. 13320 - 13325 (2004)
We have investigated the orientation dependence of the cation-π interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol-1, with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.
