Neue molekulare Knoten mit Amidstruktur: vollständige Enantiomerentrennung, chiroptische Eigenschaften, absolute Konfiguration

Vögtle, Fritz; Hünten, Annette; Vogel, Erik; Buschbeck, Sven; Safarowsky, Oliver; Recker, Janosch; Parham, Amir-Hossain; Knott, Michael; Müller, Walter M.; Müller, Ute; Kubota, Takateru; Lindner, Wolfgang; Francotte, Eric

doi:10.1002/1521-3757(20010702)113:13<2534::aid-ange2534>3.3.co;2-1

Cited by 2 publications

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“…Amide‐based catenanes,2–23 for example, cat( 1 ),11 are formed during the multicomponent condensations of aromatic (usually 1,3‐) diacid chlorides and hindered bianilines or benzylic diamines in nonpolar solvents (Scheme ). Also formed in the reactions are the corresponding un‐interlocked macrocycles (of various sizes), linear oligomers, and, at least in some cases,21, 24–26 topologically nontrivial knots.…”

Section: Introductionmentioning

confidence: 99%

The Mechanism of Formation of Amide‐Based Interlocked Compounds: Prediction of a New Rotaxane‐Forming Motif

Leigh

Venturini

Wilson

et al. 2004

Chemistry A European J

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Molecular modeling of four different reagent systems shows that the (free) energies of supramolecular interactions in the gas phase and in solution can explain the different reaction products (i.e., various sized macrocycles, catenanes, and linear oligomers) that are formed in classic amide-catenane-forming reactions. Self-assembly of the catenanes requires the formation of ordered intertwined chains and is driven by bifurcated hydrogen bonds, with pi stacking only playing a lesser role. The understanding gained from the computational study was used to predict the possibility of a new rotaxane-forming system that does not permit catenane formation. The predictions were confirmed by the successful synthesis and characterization (including X-ray crystallography) of two novel rotaxanes.

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