Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 4, Pages 1912-1919Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02524
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Funding
- National Science Foundation [CHE-1361104]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361104] Funding Source: National Science Foundation
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The reactivities of butadiene, cyclopentadiene, furan, thiophene, pyrrole, and their 1-aza- and 2-aza-derivatives in Diels-Alder reactions with ethylene and fumaronitrile were investigated with density functional theory (M06-2X/6-311G-(d,p)). The activation free energies for the Diels-Alder reactions of cyclic 1-azadienes are 10-14 kcal mol(-1) higher than those of cyclic 2-azadienes, and the reaction free energies are 17-20 kcal mol(-1) more endergonic. The distortion/interaction model shows that the increased activation energies of cyclic 1-azadienes originate from increased transition state distortion energies and unfavorable interaction energies, arising from addition to the nitrogen terminus of the C = N bond.
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