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...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2016-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.12.158 |
| _version_ | 1818446017712881664 |
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| author | Valeria Corne Ariel M. Sarotti Carmen Ramirez de Arellano Rolando A. Spanevello Alejandra G. Suárez |
| author_facet | Valeria Corne Ariel M. Sarotti Carmen Ramirez de Arellano Rolando A. Spanevello Alejandra G. Suárez |
| author_sort | Valeria Corne |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-14T19:41:02Z |
| format | Article |
| id | doaj.art-cf461d33c3544062ae46f3023820371e |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T19:41:02Z |
| publishDate | 2016-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-cf461d33c3544062ae46f3023820371e2022-12-21T22:49:43ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-07-011211616162310.3762/bjoc.12.1581860-5397-12-158Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interactionValeria Corne0Ariel M. Sarotti1Carmen Ramirez de Arellano2Rolando A. Spanevello3Alejandra G. Suárez4Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, ArgentinaInstituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, ArgentinaDepartamento de Química Orgánica, Universidad de Valencia, Valencia 46100, SpainInstituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, ArgentinaInstituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET. Suipacha 531, RosarioS2002LRK, ArgentinaChiral 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.https://doi.org/10.3762/bjoc.12.158acrylic estersasymmetric synthesisbiomassconformational equilibriumπ-stacking interaction |
| spellingShingle | Valeria Corne Ariel M. Sarotti Carmen Ramirez de Arellano Rolando A. Spanevello Alejandra G. Suárez Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction Beilstein Journal of Organic Chemistry acrylic esters asymmetric synthesis biomass conformational equilibrium π-stacking interaction |
| title | Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction |
| title_full | Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction |
| title_fullStr | Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction |
| title_full_unstemmed | Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction |
| title_short | Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction |
| title_sort | experimental and theoretical insights in the alkene arene intramolecular π stacking interaction |
| topic | acrylic esters asymmetric synthesis biomass conformational equilibrium π-stacking interaction |
| url | https://doi.org/10.3762/bjoc.12.158 |
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