n→π* interactions engender chirality in carbonyl groups

Org Lett. 2014 Jul 3;16(13):3421-3. doi: 10.1021/ol5012967. Epub 2014 Jun 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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Crystallography, X-Ray
  • Electrons
  • Ketones / chemistry
  • Models, Chemical*
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism


  • Ketones