Experimental and theoretical insights in alkenearene intramolecular pi-stacking interaction

CORNE, V.; SAROTTI, A.M.; RAMÍREZ DE ARELLANO, C.; ROLANDO A. SPANEVELLO; SUÁREZ, A.G.*

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY

BEILSTEIN-INSTITUT

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 pi-stacking interactions. Quantum chemical calculations, NMR studies and experimental evidences demonstrate the presence of an equilibrium of at least four different conformations: pi-stacked and face-to-edge, each of them in a 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.