Publication Date:
2016-07-29
Description:
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
Keywords:
acrylic estersasymmetric synthesisbiomassconformational equilibriumπ-stacking interaction
Electronic ISSN:
1860-5397
Topics:
Chemistry and Pharmacology
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