American Chemical Society
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n→π* Interactions Engender Chirality in Carbonyl Groups

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posted on 2015-12-17, 03:03 authored by Amit Choudhary, Robert W. Newberry, Ronald T. Raines
An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences.