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

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...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2016-07, Vol.12 (1), p.1616-1623
Main Authors: Corne, Valeria, Sarotti, Ariel M, Ramirez de Arellano, Carmen, Spanevello, Rolando A, Suárez, Alejandra G
Format: Article
Language:English
Subjects:
acrylic esters
asymmetric synthesis
biomass
Chemistry
conformational equilibrium
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π-stacking interaction
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Summary: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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.158