Skip to main content
Log in

Complex formation of cucurbit[6]uril with amines in the presence of different salts

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

Abstract

The complex formation of cucurbit[6]uril with cyclohexylmethylamine hydrochloride and hexylamine hydrochloride has been studied in aqueous solution using potentiometric titrations. The influence of salts like NaCl, KCl, RbCl, CsCl, BaCl2 and tetramethylammonium chloride and tetraethylammonium perchlorate on the complex formation with amines has been studied at different concentrations of these salts. With increasing salt concentration the stability constants for the complex formation with cyclohexylamine hydrochloride and hexylamine hydrochloride decreases. However, no specific influence is observable. These results show that 2:1 complexes between these salts and cucurbituril are not formed or that their concentration in solution is rather low.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Behrend, R., Meyer, E., Rusche, F.: Ueber Condensatiosprodukte aus Glycoluril und Formaldehyd. Liebigs Ann. Chem. 339, 1–37 (1905)

    Article  Google Scholar 

  2. Freeman, W.A., Mock, W.L., Shih, N.-Y.: Cucurbituril. J. Am. Chem. Soc. 103, 7367–7368 (1981)

    Article  CAS  Google Scholar 

  3. Mock, W.L., Shih, N.-Y.: Host-guest binding of cucurbituril. J. Org. Chem. 48, 3618–3619 (1983)

    Article  CAS  Google Scholar 

  4. Mock, W.L., Shih, N.-Y.: Structure and selectivity in host-guest complexes of cucurbituril. J. Org. Chem. 51, 4440–4446 (1986)

    Article  CAS  Google Scholar 

  5. Mock, W.L., Shih, N.-Y.: Organic ligand-receptor interactions between cucurbituril and alkylammonium ions. J. Am. Chem. Soc. 110, 4706–4710 (1988)

    Article  CAS  Google Scholar 

  6. Meschke, C., Buschmann, H.-J., Schollmeyer, E.: Complexes of cucurbituril with alkyl mono- and diammonium ions in aqueous formic acid studied by calorimetric titrations. Thermochim. Acta 297, 43–48 (1997)

    Article  CAS  Google Scholar 

  7. Buschmann, H.-J., Jansen, K., Schollmeyer, E.: The formation of cucurbituril complexes with amino acids and amino alcohols in aqueous formic acid studied by calorimetric titrations. Thermochim. Acta. 317, 95 (1998)

    Article  CAS  Google Scholar 

  8. Jansen, K., Buschmann, H.-J., Wego, A., Döpp, D., Mayer, C., Drexler, H.-J., Holdt, H.-J., Schollmeyer, E.: Cucurbit[5]uril, decamethylcucurbit[5]uril and cucurbit[6]uril. Synthesis, solubility, and amine complex formation. J. Incl. Phenom. Macrocyclic Chem. 39, 357–363 (2001)

    Article  CAS  Google Scholar 

  9. Buschmann, H.-J., Mutihac, L., Schollmeyer, E.: 11-Aminoundecanoic acid, cyclodextrin (α, β) and cucurbit[n]urils (n = 6, 7) as building blocks for supramolecular assemblies: a thermodynamic study. J. Incl. Phenom. Macrocyclic Chem. 56, 363–368 (2006)

    Article  CAS  Google Scholar 

  10. Rekharsky, M.V., Yamamura, H., Kawai, M., Osaka, I., Arakawa, R., Sato, A., Ko, Y.H., Selvapalam, N., Kim, K., Inoue, Y.: Sequential formation of a ternary complex among dihexylammonium, cucurbit[6]uril, and cyclodextrin with positive cooperativity. Org. Lett. 8, 815–818 (2006)

    Article  CAS  Google Scholar 

  11. Rekharsky, M.V., Ko, Y.H., Selvapalam, N., Kim, K., Inoue, Y.: Complexation thermodynamic of cucurbit[6]uril with aliphatic alcohols, amines, and diamines. Supramol. Chem. 19, 39–46 (2007)

    Article  CAS  Google Scholar 

  12. Marquez, C., Nau, W.M.: Two mechanisms of slow host-guest complexation between cucurbit[6]uril and cyclohexylmethylamine: pH-responsive supramolecular kinetics. Angew. Chem. Int. Ed. 40, 3155–3160 (2001)

    Article  CAS  Google Scholar 

  13. Marquez, C., Hudgins, R.R., Nau, W.M.: Mechanism of host-guest complexation by cucurbituril. J. Am. Chem. Soc. 126, 5806–5816 (2004)

    Article  CAS  Google Scholar 

  14. Whang, D., Jeon, Y.-M., Heo, J., Kim, K.: Self-assembly of a polyrotaxane containing a cyclic “bead” in every structural unit: cucurbituril molecules threaded on an 1D coordination polymer. J. Am. Chem. Soc. 118, 11333–11334 (1996)

    Article  CAS  Google Scholar 

  15. Whang, D., Kim, K.: Polycartenated 2D polyrotaxane net. J. Am. Chem. Soc. 119, 451–452 (1997)

    Article  CAS  Google Scholar 

  16. Meschke, C., Buschmann, H.-J., Schollmeyer, E.: Synthesis of mono-, oligo- and polyamide-cucurbituril rotaxanes. Macromol. Rapid Commun. 19, 59–63 (1998)

    Article  CAS  Google Scholar 

  17. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., Isaacs, L.: The cucurbit[n]uril family. Angew. Chem. Int. Ed. 44, 4844–4870 (2005)

    Article  CAS  Google Scholar 

  18. Freeman, W.A.: Structures of the p-xylylenediammonium chloride and calcium hydrogensulfate adducts of the cavitand “cucurbituril” C36H36N24O12. Acta Cryst. B40, 382–387 (1984)

    CAS  Google Scholar 

  19. Jeon, Y.-M., Kim, J., Whang, D., Kim, K.: A molecular container assembly capable of controlling binding and release of its guest molecules. Reversible encapsulation of organic molecules in sodium ion complexed cucurbituril. J. Am. Chem. Soc. 118, 9790–9791 (1996)

    Article  CAS  Google Scholar 

  20. Whang, D., Heo, J., Park, J.H., Kim, K.: A molecular bowl with metal ion as bottom: reversible inclusion of organic molecules in cesium ion complexed cucurbituril. Angew. Chem. Int. Ed. 37, 78–80 (1998)

    Article  CAS  Google Scholar 

  21. Heo, J., Kim, S.-Y., Whang, D., Kim, K.: Shape-induce, hexagonal, open frameworks: rubidium ion complexed cucurbituril. Angew. Chem. Int. Ed. 39, 641–643 (1999)

    Article  Google Scholar 

  22. Hoffmann, R., Knoche, W., Fenn, C., Buschmann, H.-J.: Host-guest complexes of cucurbituril with the 4-methylbenzylammonium ion, alkali-metal cations and NH+ 4. J. Chem. Soc., Faraday Trans. 90, 1507–1511 (1994)

    Article  CAS  Google Scholar 

  23. Buschmann, H.-J., Cleve, E., Schollmeyer, E.: Cucurbituril as a ligand for the complexation of cations in aqueous solutions. Inorg. Chim. Acta 193, 93–97 (1992)

    Article  CAS  Google Scholar 

  24. Buschmann, H.-J., Cleve, E., Schollmeyer, E.: in preparation

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hans-Jürgen Buschmann.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buschmann, HJ., Mutihac, L. & Schollmeyer, E. Complex formation of cucurbit[6]uril with amines in the presence of different salts. J Incl Phenom Macrocycl Chem 61, 343–346 (2008). https://doi.org/10.1007/s10847-008-9427-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-008-9427-3

Keywords

Navigation