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Pseudorotaxane intermediates comprising urea-based threads and amide-based macrocycles have been proposed in elegant one-pot rotaxane syntheses from diisocyanates, a bulky aryl amine, and amide-based macrocycles. The true recognition system in this reaction, however, was not identified; the authors stated that the mechanism of this rotaxane formation is yet not proven. See: O. Braun, F. Vögtle, Synlett 1997, 1184-1186
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Pseudorotaxane intermediates comprising urea-based threads and amide-based macrocycles have been proposed in elegant one-pot rotaxane syntheses from diisocyanates, a bulky aryl amine, and amide-based macrocycles. The true recognition system in this reaction, however, was not identified; the authors stated that "the mechanism of this rotaxane formation is yet not proven". See: O. Braun, F. Vögtle, Synlett 1997, 1184-1186.
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Amide-based macrocycles have been used to construct many elegant interlocked molecules. In most circumstances, the threading of guests into these macrocycles required the cooperation of two or more suitably positioned carbonyl groups or anionic templates; see: a
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We calculated the association constant from a 1H NMR spectroscopic dilution experiment to be 11 000 M-1; we quote the value as > 104 M-1 because of the inherent error of this approach when the dissociation constant approaches the limit of detection of 1H NMR spectroscopy
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1H NMR spectroscopy.
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34548625408
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According to reference [6, the amide-based macrocycle might also recognize isocyanates during the rotaxane synthesis
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According to reference [6], the amide-based macrocycle might also recognize isocyanates during the rotaxane synthesis.
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42
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0000011260
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For more details about this stoppering method, see
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For more details about this stoppering method, see: E. Córdova, R. A. Bissell, N. Spencer, P. R. Ashton, J. F. Stoddart, A. E. Kaifer, J. Org. Chem. 1993, 58, 6550-6552.
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84877935319
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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
CCDC 647854 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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CCDC 647854 contains the supplementary crystallographic data for this paper
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44
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34548621631
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Crystal-data for 6: C79H86O 9N6·CH2Cl2·H 2O, Mr, 1366.48, triclinic, space group P1, a, 13.0119(4, b, 14.1602(4, c, 20.4104(6) Å, V, 3662.43(19) Å3, ρcalcd, 1.239 g cm-3, μ, MoKα, 0.152 mm-1, T, 295(2)K, colorless cubes; 12883 independent measured reflections, F2 refinement, R1, 0.0708, wR 2, 0.1624
-
2 = 0.1624.
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45
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33646940418
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and ref, 12, The binding affinity of oxoanions toward urea derivatives is proportional to their basicity; see
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The binding affinity of oxoanions toward urea derivatives is proportional to their basicity; see: V. Amendola, M. Bonizzoni, D. Esteban-Gómez, L. Fabbrizzi, M. Licchelli, F. Sancenón, A. Taglietti, Coord. Chem. Rev. 2006, 250, 1451-1470, and ref. [12].
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Sancenón, F.6
Taglietti, A.7
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