title: 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.
authors.affiliation: Graduate Program in Biophysics and Departments of ‡Chemistry and §Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
authors.forename: Amit
authors.initials: A
authors.lastname: Choudhary
authors.forename: Robert W
authors.initials: RW
authors.lastname: Newberry
authors.forename: Ronald T
authors.initials: RT
authors.lastname: Raines
mesh_terms: D018360:Crystallography, X-Ray; D004583:Electrons; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007659:Ketones