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RESEARCH PRODUCT
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
Luis R. DomingoEduardo ChamorroPatricia Pérezsubject
chemistry.chemical_compoundDieneNucleophileChemistryComputational chemistryElectrophileDensity functional theoryPhysical and Theoretical ChemistryGround stateCycloadditionElectron localization functionNatural bond orbitaldescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-01-01 | The Journal of Physical Chemistry A |