I was wondering why nitriles do not react as electrophiles like carbonyl unless they have to, given that the C-N triple bond is still pretty polarized. The LUMO will be higher in energy than a carbonyl due to the higher electronegativity of oxygen, but I don't see why nitriles are far worse in electrophilicity.
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1$\begingroup$ Who says they don't? They are not as reactive as carbonyls, but there are plenty of reactions with nucleophilic attack at the nitrile carbon - example: chem.ucalgary.ca/courses/350/Carey5th/Ch20/ch20-3-5-3.html $\endgroup$– WaylanderCommented Jul 8, 2020 at 14:12
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