N??* interactions engender chirality in carbonyl groups.
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ABSTRACT:
SUBMITTER: Choudhary A
PROVIDER: S-EPMC4096190 | biostudies-other | 2014 Jul
REPOSITORIES: biostudies-other
Publications
n→π* interactions engender chirality in carbonyl groups.
Choudhary Amit A Newberry Robert W RW Raines Ronald T RT
Organic letters 20140613 13
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. ...[more]
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