title: Mechanism of electrophilic chlorination: experimental determination of a geometrical requirement for chlorine transfer by the endocyclic restriction test.
abstract: An endocyclic restriction test for acid-catalyzed transfer of chlorine from a protonated chloroamine to an aromatic ring provides data that are consistent with a transition structure with a large bond angle between the entering and leaving groups around chlorine. These results rule out a dissociative mechanism or a mechanism that has an oblique angle between the entering and leaving groups.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
authors.forename: Suk Joong
authors.initials: SJ
authors.lastname: Lee
authors.forename: Michael S
authors.initials: MS
authors.lastname: Terrazas
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Pippel
authors.forename: Peter
authors.initials: P
authors.lastname: Beak
mesh_terms: D002700:Chloramines / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D002722:Chlorobenzenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002700:Chloramines; D002722:Chlorobenzenes; D002713:Chlorine