Skip to main content
SpringerLink
Log in

Inclusion of amides by a fluorenyl diol host

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The structure of the host compound 1,4-bis(9-hydroxy-9-fluorenyl)benzene as well as the structures of the inclusion complexes with four amides, dimethylformamide (DMF), dimethylacetamide (DMA), tetramethylurea (TMU) and hexamethylphosphoramide (HMPA) have been elucidated. Each structure crystallised in a centrosymmetric space group with Z = 2 and a host to guest ratio of 1:1 or 1:2, as determined by thermogravimetric analysis. Lattice energies have been calculated by atom-atom potential methods and these results were compared to the thermal stabilities observed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Caira, M.R., Jacobs, A., Nassimbeni, L.R., Toda, F.: Complexation with diol host compounds. Part 36: inclusion compounds of 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol with benzene, toluene and mesitylene. J. Chem. Crystallogr. 36(7), 435–443 (2006). doi:10.1007/s10870-005-9042-8

    Article  CAS  Google Scholar 

  2. Caira, M.R., Jacobs, A., Nassimbeni, L.R., Toda, F.: Inclusion compounds of 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol with DMF and DMSO: structures, selectivity and kinetics of desolvation. CrystEngComm 5, 150–153 (2003). doi:10.1039/b302548a

    Article  CAS  Google Scholar 

  3. Bond, D.R., Johnson, L., Nassimbeni, L.R., Toda, F.J.: Complexation with diol host compounds. Part 6. Structure and dynamics of enclathration by 1,1,6,6-tetraphenyl-hexa-2,4-diyne-1,6-diol. Solid State Chem. 92(1), 68–79 (1991). doi:10.1016/0022-4596(91)90243-B.

    Article  CAS  Google Scholar 

  4. Weber, E., Nitsche, S., Wierig, A., Csöregh, I.: Inclusion compounds of diol hosts featuring two 9-Hydroxy-9-fluorenyl or analogous groups attached to linear spacer units. Eur. J. Org. Chem. 2002(5), 856–872 (2002). doi:10.1002/1099-0690(200203)2002:5<856::AID-EJOC856>3.0.CO;2-R

    Article  Google Scholar 

  5. Weber, E.: MacNicol, D.D., Toda, F., Bishop, R. (eds.) Shape and symmetry in the design of new hosts. Comprehensive Supramolecular Chemistry, vol. 6, Chap. 17. Pergamon, Oxford (1996)

  6. Weber, E.: In: Atwood, J.L., Davies, J.E.D., MacNicol, D.D. (eds.) Scissor type hosts: molecular design and inclusion behaviour. Inclusion Compounds, vol. 4, Chap. 5. Oxford University Press, Oxford (1991)

  7. Bacchi, A., Bosetti, E., Carcelli, M., Pelagatti, P., Rogolino, D., Pelizzi, G.: “Venetian blinds” mechanism of solvation/desolvation in Palladium(II) wheel-and-axle organic-inorganic diols. Inorg. Chem. 44(2), 431–442 (2005). doi:10.1021/ic048896m

    Article  CAS  Google Scholar 

  8. Bacchi, A., Bosetti, E., Carcelli, M.: Engineering organic/inorganic diols that reversibly capture and release volatile guests. CrystEngComm 7, 527–537 (2005). doi:10.1039/b507966g

    CAS  Google Scholar 

  9. Hooft, R.: COLLECT. Data Collection Software. Nonius BV, Delft, The Netherlands (1998)

    Google Scholar 

  10. Otwinowski, Z., Minor, W.: Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 276, 307–326 (1997). doi:10.1016/S0076-6879(97)76066-X

    Article  CAS  Google Scholar 

  11. Sheldrick, G.M.: SHELXS86. In: Sheldrick, G.M., Kruger, C., Goddard, P. (eds.) Crystallographic Computing, pp. 3–175. Oxford University Press, Oxford (1985)

    Google Scholar 

  12. Sheldrick, G.M.: SHELXL-97. University of Göttingen, Germany (1997)

    Google Scholar 

  13. Barbour, L.J.: X-Seed—A software tool for supramolecular crystallography. J. Supramol. Chem. 1, 189–191 (2001). doi:10.1016/S1472-7862(02)00030-8

    Article  CAS  Google Scholar 

  14. Atwood, J.L., Barbour, L.J.: Molecular graphics: from science to art. Cryst. Growth Des. 3, 3–8 (2003). doi:10.1021/cg020063o

    Article  CAS  Google Scholar 

  15. Gavezzotti, A.: OPIX. University of Milan, Italy (2003)

    Google Scholar 

  16. McKinnon, J.J., Spackman, M.A., Mitchell, A.S.: Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Crystallogr. B B60(6), 627–668 (2004). doi:10.1107/S0108768104020300

    Article  CAS  Google Scholar 

  17. Spackman, M.A., McKinnon, J.J.: Fingerprinting intermolecular interactions in molecular crystals. Cryst. Eng. Comm 4, 378–392 (2002). doi:10.1039/b203191b

    Article  CAS  Google Scholar 

  18. Wolff, S.K., Grimwood, D.J., McKinnon, J.J., Jayatilaka, D., Speckman, M.A.: CrystalExplorer 2.0. University of Western Australia, Perth, Australia (2005–2007)

  19. Caira, M.R., Nassimbeni, L.R., Vujovic, D., Weber, E., Wierig, A.: Separation of lutidine isomers by inclusion. Struct. Chem. 10, 205–211 (1999). doi:10.1023/A:1021836513608

    Article  CAS  Google Scholar 

Download references

Acknowledgments

EDV and LRN thank the National Research Foundation of Pretoria and the University of Cape Town for financial assistance.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Cape Town, Rondebosch 7701, Cape Town, South Africa

    Elise J. C. de Vries & Luigi R. Nassimbeni

  2. Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, 09596, Freiberg, Sachsen, Germany

    Edwin Weber

Authors
  1. Elise J. C. de Vries
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Luigi R. Nassimbeni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Edwin Weber
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Elise J. C. de Vries.

Rights and permissions

Reprints and permissions

About this article

Cite this article

de Vries, E.J.C., Nassimbeni, L.R. & Weber, E. Inclusion of amides by a fluorenyl diol host. J Incl Phenom Macrocycl Chem 63, 203–210 (2009). https://doi.org/10.1007/s10847-008-9508-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-008-9508-3

Keywords

Search

Navigation