CH···O Hydrogen Bonds in “Clicked” Diketopiperazine-Based Amide Rotaxanes

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”. 1H and 2D NMR spectra provide evidence for two different H-bonding motifs, in one of which the triazol...

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Bibliographic Details
Published in:Organic letters 2011-09, Vol.13 (18), p.4838-4841
Main Authors: Dzyuba, Egor V, Kaufmann, Lena, Löw, Nora L, Meyer, Annika K, Winkler, Henrik D. F, Rissanen, Kari, Schalley, Christoph A
Format: Article
Language:English
Subjects:
Amides - chemistry
Click Chemistry
Diketopiperazines - chemistry
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Rotaxanes - chemistry
Stereoisomerism
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Summary: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”. 1H 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201915j