Takudrei

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.

Title158
CH•••O Hydrogen Bonds in "Clicked" Diketopiperazine-Based Amide Rotaxanes
AuthorE. V. Dzyuba, L. Kaufmann, N. L. Löw, A. K. Meyer, H. D. F. Winkler, K. Rissanen, C. A. Schalley
Date20110816
IdentifierDOI 10.1021/ol201915j
Source(s)
CitationOrg. Lett. 2011, 13, 4838-4841