title: Experimental and theoretical insights in the alkene-arene intramolecular π-stacking interaction.
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.
authors: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, Argentina.
authors: Valeria
authors: V
authors: Corne
authors: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, Argentina.
authors: Ariel M
authors: AM
authors: Sarotti
authors: Departamento de Química Orgánica, Universidad de Valencia, Valencia 46100, Spain.
authors: Carmen
authors: C
authors: Ramirez de Arellano
authors: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, Argentina.
authors: Rolando A
authors: RA
authors: Spanevello
authors: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, Argentina.
authors: Alejandra G
authors: AG
authors: Suárez
keywords: acrylic esters; asymmetric synthesis; biomass; conformational equilibrium; π-stacking interaction