Resumen
The electrophilic/nucleophilic behavior of dimethyl 2,3- dimethylenesuccinate 1, an electron-deficient 2,3-disubstituted 1,3-butadiene, in polar Diels-Alder reactions has been studied using DFT methods at the B3LYP/ 6-31G(d) level of theory. The electronic nature of bonding of the transition structures involved in the cycloaddition reactions of the diene 1 toward the nucleophilically activated dienophile 6 and the strong electrophilically activated dienophile 7 has been carefully examined within the natural bond orbital (NBO) and the topological analysis of the electron localization function (ELF) frameworks. Additionally, a study of the global electrophilicity pattern of the reagents at the ground state was performed. This evidence allows us to rationalize the participation of electron-deficient 2-susbtituted and 2,3-disubstituted 1,3-butadienes as nucleophiles in polar Diels-Alder reactions.
| Idioma original | English |
|---|---|
| Páginas (desde-hasta) | 4046-4053 |
| Número de páginas | 8 |
| Publicación | Journal of Physical Chemistry A |
| Volumen | 112 |
| N.º | 17 |
| DOI | |
| Estado | Published - 1 may 2008 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
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An understanding of the electrophilic/nucleophilic behavior of electro-deficient 2,3-disubstituted 1,3-butadienes in polar Diels-Alder reactions. A density functional theory study. / Domingo, Luis R.; Chamorro, Eduardo; Pérez, Patricia.
En: Journal of Physical Chemistry A, Vol. 112, N.º 17, 01.05.2008, p. 4046-4053.Resultado de la investigación: Article
TY - JOUR
T1 - An understanding of the electrophilic/nucleophilic behavior of electro-deficient 2,3-disubstituted 1,3-butadienes in polar Diels-Alder reactions. A density functional theory study
AU - Domingo, Luis R.
AU - Chamorro, Eduardo
AU - Pérez, Patricia
PY - 2008/5/1
Y1 - 2008/5/1
N2 - The electrophilic/nucleophilic behavior of dimethyl 2,3- dimethylenesuccinate 1, an electron-deficient 2,3-disubstituted 1,3-butadiene, in polar Diels-Alder reactions has been studied using DFT methods at the B3LYP/ 6-31G(d) level of theory. The electronic nature of bonding of the transition structures involved in the cycloaddition reactions of the diene 1 toward the nucleophilically activated dienophile 6 and the strong electrophilically activated dienophile 7 has been carefully examined within the natural bond orbital (NBO) and the topological analysis of the electron localization function (ELF) frameworks. Additionally, a study of the global electrophilicity pattern of the reagents at the ground state was performed. This evidence allows us to rationalize the participation of electron-deficient 2-susbtituted and 2,3-disubstituted 1,3-butadienes as nucleophiles in polar Diels-Alder reactions.
AB - The electrophilic/nucleophilic behavior of dimethyl 2,3- dimethylenesuccinate 1, an electron-deficient 2,3-disubstituted 1,3-butadiene, in polar Diels-Alder reactions has been studied using DFT methods at the B3LYP/ 6-31G(d) level of theory. The electronic nature of bonding of the transition structures involved in the cycloaddition reactions of the diene 1 toward the nucleophilically activated dienophile 6 and the strong electrophilically activated dienophile 7 has been carefully examined within the natural bond orbital (NBO) and the topological analysis of the electron localization function (ELF) frameworks. Additionally, a study of the global electrophilicity pattern of the reagents at the ground state was performed. This evidence allows us to rationalize the participation of electron-deficient 2-susbtituted and 2,3-disubstituted 1,3-butadienes as nucleophiles in polar Diels-Alder reactions.
UR - http://www.scopus.com/inward/record.url?scp=45249085292&partnerID=8YFLogxK
U2 - 10.1021/jp711704m
DO - 10.1021/jp711704m
M3 - Article
C2 - 18370427
AN - SCOPUS:45249085292
VL - 112
SP - 4046
EP - 4053
JO - Journal of Physical Chemistry A
JF - Journal of Physical Chemistry A
SN - 1089-5639
IS - 17
ER -