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Volumn 10, Issue 9, 2008, Pages 1739-1742

A cation-directed switch of intermolecular spin-spin interaction of guanosine derivatives functionalized with open-shell units

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EID: 57249108151     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8003832     Document Type: Article
Times cited : (22)

References (32)
  • 1
    • 84967006964 scopus 로고    scopus 로고
    • Miller, J. S, Drillon M, Eds, Wiley-VCH: Weinheim, Vols
    • Magnetism: Molecules to Materials: Miller, J. S., Drillon M., Eds,; Wiley-VCH: Weinheim, 2001 -2003; Vols. I-IV.
    • (2001) Magnetism: Molecules to Materials , vol.I-IV
  • 8
    • 37049083607 scopus 로고    scopus 로고
    • Metal-induced conformational modifications in paramagnetic calixarenes have also been reported. Araki, K.; Nakamura, R.; Otsuka, H.; Shinkai, S. Chem. Commun. 1995, 2121.
    • Metal-induced conformational modifications in paramagnetic calixarenes have also been reported. Araki, K.; Nakamura, R.; Otsuka, H.; Shinkai, S. Chem. Commun. 1995, 2121.
  • 18
    • 58149177966 scopus 로고    scopus 로고
    • The low intensity negative couplet present also before K-Pic addition in the CD spectrum is due to Na, or K, contamination resulting from the synthetic procedure. In fact, addition of cryptand [2.2.2, which efficiently binds K, and Na , leads to a very weak spectrum as expected for an uncomplexed guanosine derivative
    • +), leads to a very weak spectrum as expected for an uncomplexed guanosine derivative.
  • 23
    • 0021093579 scopus 로고    scopus 로고
    • An estimate of interspin distance can be obtain by measuring the relative intensity of the |δms, 1 and |δms, 2. Eaton, S. S, More, K. M, Sawant, B. M, Eaton, G. R, Am. Chem. Soc. 1983, 105, 6560
    • s| = 2. Eaton, S. S.; More, K. M.; Sawant, B. M.; Eaton, G. R /. Am. Chem. Soc. 1983, 105, 6560.
  • 25
    • 58149188681 scopus 로고    scopus 로고
    • Unfortunately, we were not able to detect any signal for the half-field transition up to 77 K.
    • Unfortunately, we were not able to detect any signal for the half-field transition up to 77 K.
  • 27
    • 58149196963 scopus 로고    scopus 로고
    • The possibility for guanosine derivatives to extract more potassium or sodium than required by the templation in the inner cavity as well as the effect of water washing have been already described.7,10
    • 7,10
  • 29
    • 58149195598 scopus 로고    scopus 로고
    • After solid-liquid extraction lipophilic guanosines exist only in aggregated complexes in non polar solvents (e.g, CDC13, while in more polar solvents (e.g, CD3CN) NMR spectra do show an equilibrium mixture of alkali ion templated complexes and monomeric species in slow exchange on the NMR chemical shift time scale. 6,10,14,18
    • 6,10,14,18
  • 32
    • 58149200324 scopus 로고    scopus 로고
    • 19 However, increasing the acidity of the solution leads to the disappearance of the EPR signal, because of the reduction of the nitroxide moiety to a diamagnetic unit. Nevertheless, CD experiments showed that reversible conversion between octameric and uncomplexed forms is still operating under these conditions (see Figure S14, Supporting Information).
    • 19 However, increasing the acidity of the solution leads to the disappearance of the EPR signal, because of the reduction of the nitroxide moiety to a diamagnetic unit. Nevertheless, CD experiments showed that reversible conversion between octameric and uncomplexed forms is still operating under these conditions (see Figure S14, Supporting Information).


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