Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction (Beilstein Journal of Organic Chemistry)

Abstract Chiral acrylic esters derived from biomass were developed as models to have a better insight in the aryl–vinyl π-stacking interactions. Quantum chemical calculations, NMR studies and experimental evidences demonstrated the presence of equilibriums of at least four different conformations: π-stacked and face-to-edge, each of them in an s-cis/s-trans conformation. The results show that the stabilization produced by the π–π interaction makes the π-stacked conformation predominant in solution and this stabilization is slightly affected by the electron density of the aromatic counterpart. Beilstein J. Org. Chem. 2016, 12, 1616–1623. doi:10.3762/bjoc.12.158