Experimental and theoretical insights in the alkene-arene intramolecular π-stacking interaction

Chiral acrylic esters derived from biomass were developed as models to have a better insight in the aryl-vinyl pi-stacking interactions. Quantum chemical calculations, NMR studies and experimental evidences demonstrated the presence of equilibriums of at least four different conformations: pi-stacked and face-to-edge, each of them in an s-cis/s-trans conformation. The results show that the stabilization produced by the pi-pi interaction makes the pi-stacked conformation predominant in solution and this stabilization is slightly affected by the electron density of the aromatic counterpart.