Heterocycles with a-carbonyl groups are useful enzyme inhibitors, for example reacting with serine residues to form hemi-ketal adducts.  We have sought to evaluate the electrophilic reactivities of carbonyl groups in heterocyclic compounds.  Specifically, we have been interested in probing electronic and structural effects that influence the position of carbonyl/hemi-acetal or hemi-ketal equilibria.  For example, calculated LUMO levels may be roughly correlated to the electrophilic reactivity of a carbonyl group and the position of the equilibria:

On the electrophilic reactivities of α-carbonyl heterocycles

243rd National Meeting (2012)

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