Ene Reaction - Enophile

Enophile

Enophiles are π-bonded molecules which have electron-withdrawing substituents that lower significantly the LUMO of the π-bond. Possible enophiles contain carbon-carbon multiple bonds (olefins, acetylenes, benzynes), carbon-hetero multiple bonds (C=O in the case of carbonyl-ene reactions, C=N, C=S, C≡P), hetero-hetero multiple bonds (N=N, O=O, Si=Si, N=O, S=O), cumulene systems (N=S=O, N=S=N, C=C=O, C=C=S, SO2) and charged π systems (C=N+, C=S+, C≡O+, C≡N+).

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Other articles related to "enophile":

Ene Reaction - Mechanism - Concerted Pathway and Transition States
... the HOMO of the ene and the LUMO of the enophile (Figure 2) ... However, if the enophile becomes more polar (going from ethane to formaldehyde), its LUMO has a larger amplitude on C, yielding a better C–C overlap and a worse H–O one, determining the reaction to proceed. 14.7 kcal/mol (M06-2X/def2-TZVPP), if S replaces O on the enophile ...