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N→π* interactions engender chirality in carbonyl groups.

ABSTRACT: 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.

SUBMITTER: Choudhary A

PROVIDER: S-EPMC4096190 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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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]

PMID: 24926562

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