title: CH···O hydrogen bonds in "clicked" diketopiperazine-based amide rotaxanes.
abstract: Two amide [2]rotaxanes were synthesized in high yields using a novel N,N'-dipropargyl diketopiperazine axle centerpiece as the template to which the stoppers are attached through "click chemistry". (1)H and 2D NMR spectra provide evidence for two different H-bonding motifs, in one of which the triazole CH groups form C-H···O═C bonds with the wheel carbonyl O atoms. This motif can be controlled and switched reversibly by competitive anion binding.
authors.affiliation: Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany.
authors.forename: Egor V
authors.initials: EV
authors.lastname: Dzyuba
authors.forename: Lena
authors.initials: L
authors.lastname: Kaufmann
authors.forename: Nora L
authors.initials: NL
authors.lastname: Löw
authors.forename: Annika K
authors.initials: AK
authors.lastname: Meyer
authors.forename: Henrik D F
authors.initials: HD
authors.lastname: Winkler
authors.forename: Kari
authors.initials: K
authors.lastname: Rissanen
authors.forename: Christoph A
authors.initials: CA
authors.lastname: Schalley
mesh_terms: D000577:Amides / Q000737:chemistry*; D057930:Click Chemistry; D054659:Diketopiperazines / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D043862:Rotaxanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D054659:Diketopiperazines; D043862:Rotaxanes