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Volumn 46, Issue 35, 2007, Pages 6629-6633

Using acetate anions to induce translational isomerization in a neutral urea-based molecular switch

Author keywords

Anion recognition; Host guest systems; Molecular switches; Rotaxanes urea

Indexed keywords

BINDING SITES; DERIVATIVES; ISOMERIZATION; NEGATIVE IONS; UREA;

EID: 34548659123     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702197     Document Type: Article
Times cited : (108)

References (45)
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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
    • 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
    • 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) G. A. Breault, C. A. Hunter, P. C. Mayers, Tetrahedron 1999, 55, 5265-5293;
    • (1999) Tetrahedron , vol.55 , pp. 5265-5293
    • Breault, G.A.1    Hunter, C.A.2    Mayers, P.C.3
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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
    • 1H NMR spectroscopy.
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    • For the influence of solvent on noncovalent interactions, see
    • For the influence of solvent on noncovalent interactions, see: C. A. Hunter, Angew. Chem. 2004, 116, 5424-5439;
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    • For more details regarding the recognition of urea derivatives to acetate anions, see: a
    • For more details regarding the recognition of urea derivatives to acetate anions, see: a) M. P. Hughes, B. D. Smith, J. Org. Chem. 1997, 62, 4492-4499;
    • (1997) J. Org. Chem , vol.62 , pp. 4492-4499
    • Hughes, M.P.1    Smith, B.D.2
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    • According to reference [6, the amide-based macrocycle might also recognize isocyanates during the rotaxane synthesis
    • According to reference [6], the amide-based macrocycle might also recognize isocyanates during the rotaxane synthesis.
  • 43
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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.
    • CCDC 647854 contains the supplementary crystallographic data for this paper
  • 44
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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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.