ol5012967_si_010.cif (547.68 kB)
n→π* Interactions Engender Chirality in Carbonyl Groups
dataset
posted on 2015-12-17, 03:03 authored by Amit Choudhary, Robert
W. Newberry, Ronald T. RainesAn 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.