Advertisement

Molecular Motions in Catenands and Catenates Studied by 13C NMR Relaxation Times

  • J.-P. Kintzinger
  • H. Bourgeois
  • A. Edel
  • R. Graff
  • J.-C. Chambron
  • C. O. Dietrich-Buchecker
  • J.-P. Sauvage
Chapter
  • 113 Downloads
Part of the NATO ASI Series book series (ASIC, volume 426)

Abstract

Molecular motions in catenands and catenates were studied by 13C NMR relaxation times and were compared to those of the free macrocycles. The macrocycles are less mobile when interlocked in a catenand or in a catenate. The internal mobility is also affected and shows where the contacts between the rings take place. Experimental evidence is given for the existence of some internal motion of one macrocycle relative to the other.

Keywords

Correlation Time Internal Motion Phenyl Substituent Internal Mobility Polyoxyethylenic Chain 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    a) C.O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev., 1987, 87, 795–810.CrossRefGoogle Scholar
  2. (b).
    J.-P. Sauvage, Acc. Chem. Res., 1990, 23, 319–327.CrossRefGoogle Scholar
  3. (c).
    C.O. Dietrich-Buchecker, J.-P. Sauvage, Tetrahedron, 1990, 46, 503–512.CrossRefGoogle Scholar
  4. [2] (a) H.L. Frisch, E. Wasserman, J. Am. Chem. Soc., 1961, 83, 3789–3795. (b)
    D.M. Walba, Tetrahedron, 1985, 41, 3141–3212.CrossRefGoogle Scholar
  5. [3]
    H. Fritz, P. Hug, H. Sauter, E. Logemann, J. Mag. Resort., 1976, 21, 373–375.Google Scholar
  6. [4]
    Ortholand J.-Y., Slawin A.M.Z., Spencer N., Stoddart J.F., Williams DJ., Angew. Chem. Int. Ed. Engl., 1989, 28, 1394; Aston P.R., Goodnow, T.T., Kaifer A.E., Eddington M., Slawin A.M.Z., Spencer N., Stoddart J.F., Vicent C., Williams D.J., Angew. Chem. Int. Ed. Engl., 1989, 28, 1396.CrossRefGoogle Scholar
  7. [5]
    a) H. Bourgeois, Diplôme d’Etudes Approfondies, Université Louis Pasteur, Strasbourg, 1991. (b) A. Edel, Thèse de doctorat de l’Université Louis-Pasteur, Strasbourg, 1986.Google Scholar
  8. [6] (a) C.O. Dietrich-Buchecker, J.-P. Sauvage, Tetrahedron Lett., 1983, 24, 5091–5094. (b) C.O. Dietrich-Buchecker, J.-P. Sauvage, J.-M. Kern, J. Am. Chem. Soc., 1984, 106, 3043–3045. (c) C.O. Dietrich-Buchecker, J.-P. Sauvage, J.-P. Kintzinger, Tetrahedron Lett., 1983, 24, 5095–5098: (d)
    C.O. Dietrich-Buchecker, J.-P. Sauvage, J.-M. Kern, J. Am. Chem. Soc., 1989, 111, 7791–7800.CrossRefGoogle Scholar
  9. [7]
    J.-C. Chambron, D.K. Mitchell, J.-P; Sauvage, J. Am. Chem. Soc., 1992, 114, 4625–4631.CrossRefGoogle Scholar
  10. [8] (a) R.L. Vold, J.S. Waugh, M.P. Klein, D.E. Phelps, J. Chem. Phys., 1968, 48, 3831–3832. (b) D. Canet, G.C Levy, I.R. Peat, J. Magn. Reson., 1975, 18, 199–204. (c)
    J. Granot, J. Magn. Reson., 1983, 53, 386–397.Google Scholar
  11. [9] (a) I. Solomon, Phys. Rev. 1955, 99, 559–565; (b)
    T.D. Alger, S.W. Collins, D.M. Grant, J. Chem. Phys., 1971, 54, 2820–2827.CrossRefGoogle Scholar
  12. [10]
    A measure at 7.05 T, on a solution of 3 in d7-dmf gives a T1 = 2.65 s for C1a, C10a whereas carbon atoms 3/8; 4/7; 5/6 have a T1 equal to 0.21 s. Taking in account the chemical shift anisotropy contribution should raise the dipolar contribution to 0.23 s which is considered as negligible.Google Scholar
  13. [11]
    M. Cesario, C.O. Dietrich-Buchecker, J. Guilhem, C. Pascard, J.-P. Sauvage, J. Chem. Soc., Chem. Commun., 1985, 244–247.Google Scholar
  14. [12]
    D. Doddrell, A. Allerhand, J. Am. Chem. Soc., 1971, 93, 1558–1559.CrossRefGoogle Scholar
  15. [13] (a) P. Debye, Polare Molekulen, Verlag von S. Hirzel, Leipzig (1929); (b) N. Bloembergen, Thesis, Leiden (1948); (c)
    N. Bloembergen, E.M. Purcell, R.V. Pound, Phys. Rev., 1948, 73, 679–712.CrossRefGoogle Scholar
  16. [14]
    N. Morel-Desrosiers, J.-P. Morel, C.O. Dietrich-Buchecker, J. Weiss, J.-P. Sauvage, New J. Chem., 1988, 12, 205–208.Google Scholar
  17. [15]
    A. Edel, J.-P. Kintzinger, R. Graff, C.O. Dietrich-Buchecker, J.-Cl. Chambron, J.-P. Sauvage, in preparation.Google Scholar
  18. [16]
    G. Lipari, A. Szabo, J. Am. Chem. Soc., 1982, 104, 4546 - 4559.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1994

Authors and Affiliations

  • J.-P. Kintzinger
    • 1
  • H. Bourgeois
    • 1
  • A. Edel
    • 1
  • R. Graff
    • 2
  • J.-C. Chambron
    • 3
    • 4
  • C. O. Dietrich-Buchecker
    • 3
    • 4
  • J.-P. Sauvage
    • 3
    • 4
  1. 1.Laboratoire de RMN et de Modélisation MoléculaireUMR 50 du CNRSFrance
  2. 2.Service Commun de RMNFrance
  3. 3.Laboratoire de Chimie Organo-MinéraleURA 422 du CNRSFrance
  4. 4.Institut de ChimieUniversité Louis PasteurStrasbourgFrance

Personalised recommendations