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

CORNE, V.; SAROTTI, A. M.; RAMIREZ DE ARELLANO, C.; SPANEVELLO, R. A.; SUÁREZ, A. G.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY

BEILSTEIN-INSTITUT

Lugar: Francfurt; Año: 2016 vol. 12 p. 1616 - 1623

1860-5397

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 demonstrate the presence of an equilibrium of at least four different conformations: π-stacked and face-to-edge, each of them in a 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.