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158
CH•••O Hydrogen Bonds in "Clicked" Diketopiperazine-Based Amide Rotaxanes

E. V. Dzyuba, L. Kaufmann, N. L. Löw, A. K. Meyer, H. D. F. Winkler, K. Rissanen, C. A. Schalley – 2011

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.

Title
158
CH•••O Hydrogen Bonds in "Clicked" Diketopiperazine-Based Amide Rotaxanes
Author
E. V. Dzyuba, L. Kaufmann, N. L. Löw, A. K. Meyer, H. D. F. Winkler, K. Rissanen, C. A. Schalley
Date
2011-08-16
Identifier
DOI 10.1021/ol201915j
Citation
Org. Lett. 2011, 13, 4838-4841