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• W2291934513 abstract "The combination of H2C═NH and cis-1,3-butadiene to form a six-membered ring was examined by quantum calculations. The energy barrier for this reaction is substantially lowered by the introduction of an imidazolium catalyst with either a H or halogen (X) atom in the 2-position, which acts via a H or halogen bond to the N atom of the imine, respectively. X = I has the largest effect, and Cl the smallest; Br and H are roughly equivalent. The catalyst retards the formation of the incipient N–C bond from imine to diene while simultaneously accelerating the C–C bond formation. The energy of the π* LUMO of the imine is lowered by the catalyst, which thereby enhances charge transfer from the diene to the imine. Assessment of free energies suggests catalytic rate acceleration by as much as 4–6 orders of magnitude." @default.
• W2291934513 created "2016-06-24" @default.
• W2291934513 creator A5084102535 @default.
• W2291934513 creator A5085422555 @default.
• W2291934513 date "2016-03-03" @default.
• W2291934513 modified "2023-10-16" @default.
• W2291934513 title "Catalysis of the Aza-Diels–Alder Reaction by Hydrogen and Halogen Bonds" @default.
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• W2291934513 doi "https://doi.org/10.1021/acs.joc.6b00344" @default.
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