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

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Abstract

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.

Original languageEnglish
Pages (from-to)4046-4053
Number of pages8
JournalJournal of Physical Chemistry A
Volume112
Issue number17
DOIs
Publication statusPublished - 1 May 2008

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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