title: Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution.
abstract: A general platform for the synthesis of various chiral halogen-bond (XB) donors based on the triazole core and the characterisation of factors that influence the strength of the halogen bond in the solid state and in solution are reported. The characterisation of XB donors in the solid state by X-ray crystallography and in solution by1H NMR titration can be used to aid the design of new XB donors. We describe the first example of a XB between iodotriazoles and thioureas in solution. In addition, the enantiodiscrimination of acceptors in solution through halogen-bond participation is described.
authors.affiliation: Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors.forename: Mikk
authors.initials: M
authors.lastname: Kaasik
authors.affiliation: Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors.forename: Sandra
authors.initials: S
authors.lastname: Kaabel
authors.affiliation: Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors.forename: Kadri
authors.initials: K
authors.lastname: Kriis
authors.affiliation: Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors.forename: Ivar
authors.initials: I
authors.lastname: Järving
authors.affiliation: Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors.forename: Riina
authors.initials: R
authors.lastname: Aav
authors.affiliation: Department of Chemistry, University of Jyvaskula, Nanoscience Center, P.O. Box 35, 40014, Jyvaskyla, Finland.
authors.forename: Kari
authors.initials: K
authors.lastname: Rissanen
authors.affiliation: Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.
authors.forename: Tõnis
authors.identifier: http://orcid.org/0000-0001-5339-9682
authors.initials: T
authors.lastname: Kanger
keywords: NMR titrations; X-ray diffraction; donor-acceptor systems; halogen bonds; heterocycles