title: Dynamic origin of the stereoselectivity of a nucleophilic substitution reaction.
abstract: A nucleophilic substitution on a dichlorovinyl ketone was studied experimentally and computationally. A mixture of products is observed experimentally, but a conventional computational analysis does not account for the formation of the minor stereoisomer. Instead, the product mixture is predicted accurately from a dynamic trajectory study on a bifurcating energy surface. The dynamic origin of the stereoselectivity of the reaction is discussed.
authors.affiliation: Department of Chemistry, Texas A&M University , PO Box 30012, College Station, Texas 77842, United States.
authors.forename: Xavier S
authors.initials: XS
authors.lastname: Bogle
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Singleton
mesh_terms: D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D006843:Hydrocarbons, Chlorinated; D007659:Ketones; D014753:Vinyl Compounds; C587802:dichlorovinyl ketone