Effect of Aryl Substituents on the Reactivity of the Captodative Olefins 1-Acetylvinyl Arenecarboxylates
Fuente:
Redalyc
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Artículo científico |
| Sprache: | en |
| Veröffentlicht: |
Sociedad Química de México
2006
|
| Schlagworte: | |
| Online-Zugang: | |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| _version_ | 1876476099285745664 |
|---|---|
| author | Enrique García-Pérez |
| author_facet | Enrique García-Pérez |
| contents | Effect of Aryl Substituents on the Reactivity of the Captodative Olefins 1-Acetylvinyl Arenecarboxylates Enrique García-Pérez Jorge A. Mendoza Hugo A. Jiménez-Vázquez Joaquín Tamariz Multidisciplinaria (Ciencias Naturales y Exactas) FMO Hammett constants inductive effects Captodative olefins acetylvinyl arenecarboxylates With the aim of evaluating the effect of substitution at thearyl moiety of the aroyloxy group of captodative olefins 1 on theirreactivity in Diels-Alder and other reactions, the new series of olefins1-acetylvinyl arenecarboxylates 1c1k were prepared. No correlationwas found between 13C NMR chemical shifts of the carbon atoms ofthe double bond and the electronic effects of the diverse substituents.However, an excellent correlation was observed between the energiesof the FMOs (HF/6-31G*), or the corresponding atomic coefficientsor the Mülliken charges at the carbon atoms of the double bond, andthe Hammett σm and σp constants of the phenyl ring substituents ofsome members of the series, and of some other calculated analogues.These results strongly suggest that, in addition to the major effect ofthe electron-withdrawing group, the reactivity of captodative olefins1 is also controlled by the long-range inductive effects of the substituentat the phenyl ring of the aroyloxy group. 2006 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47550201 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.50 |
| format | Artículo científico |
| id | redalyc_47550201 |
| institution | Redalyc |
| language | en |
| publishDate | 2006 |
| publisher | Sociedad Química de México |
| spellingShingle | Effect of Aryl Substituents on the Reactivity of the Captodative Olefins 1-Acetylvinyl Arenecarboxylates Enrique García-Pérez Multidisciplinaria (Ciencias Naturales y Exactas) FMO Hammett constants inductive effects Captodative olefins acetylvinyl arenecarboxylates Effect of Aryl Substituents on the Reactivity of the Captodative Olefins 1-Acetylvinyl Arenecarboxylates Enrique García-Pérez Jorge A. Mendoza Hugo A. Jiménez-Vázquez Joaquín Tamariz Multidisciplinaria (Ciencias Naturales y Exactas) FMO Hammett constants inductive effects Captodative olefins acetylvinyl arenecarboxylates With the aim of evaluating the effect of substitution at thearyl moiety of the aroyloxy group of captodative olefins 1 on theirreactivity in Diels-Alder and other reactions, the new series of olefins1-acetylvinyl arenecarboxylates 1c1k were prepared. No correlationwas found between 13C NMR chemical shifts of the carbon atoms ofthe double bond and the electronic effects of the diverse substituents.However, an excellent correlation was observed between the energiesof the FMOs (HF/6-31G*), or the corresponding atomic coefficientsor the Mülliken charges at the carbon atoms of the double bond, andthe Hammett σm and σp constants of the phenyl ring substituents ofsome members of the series, and of some other calculated analogues.These results strongly suggest that, in addition to the major effect ofthe electron-withdrawing group, the reactivity of captodative olefins1 is also controlled by the long-range inductive effects of the substituentat the phenyl ring of the aroyloxy group. 2006 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47550201 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.50 |
| title | Effect of Aryl Substituents on the Reactivity of the Captodative Olefins 1-Acetylvinyl Arenecarboxylates |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) FMO Hammett constants inductive effects Captodative olefins acetylvinyl arenecarboxylates |
| url | https://www.redalyc.org/articulo.oa?id=47550201 |