title: Intramolecular halogen bonding supported by an aryldiyne linker.
abstract: Intramolecular halogen bonds between aryl halide donors and suitable acceptors, such as carbonyl or quinolinyl groups, held in proximity by 1,2-aryldiyne linkers, provide triangular structures in the solid state. Aryldiyne linkers provide a nearly ideal template for intramolecular halogen bonding as minor deviations from alkyne linearity can accommodate a variety of halogen bonding interactions, including O···Cl, O···Br, O···I, N···Br, and N···I. Halogen bond lengths for these units, observed by single crystal X-ray crystallography, range from 2.75 to 2.97 Å. Internal bond angles of the semirigid bridge between halogen bond donor and acceptor are responsive to changes in the identity of the halogen, the identity of the acceptor, and the electronic environment around the halogen, with the triangles retaining almost perfect co-planarity in even the most strained systems. Consistency between experimental results and structures predicted by M06-2X/6-31G* calculations demonstrates the efficacy of this computational method for modeling halogen-bonded structures of this type.
authors.affiliation: Department of Chemistry, University of Wisconsin-Stevens Point , 2001 Fourth Avenue, Stevens Point, Wisconsin 54481, United States.
authors.forename: Danielle L
authors.initials: DL
authors.lastname: Widner
authors.forename: Qianwei R
authors.initials: QR
authors.lastname: Knauf
authors.forename: Mark T
authors.initials: MT
authors.lastname: Merucci
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Fritz
authors.forename: Jon S
authors.initials: JS
authors.lastname: Sauer
authors.forename: Erin D
authors.initials: ED
authors.lastname: Speetzen
authors.forename: Eric
authors.initials: E
authors.lastname: Bosch
authors.forename: Nathan P
authors.initials: NP
authors.lastname: Bowling