Skip to main content
SpringerLink
Log in

Qualitative comparison between the quantum calculations and electrospray mass spectra o complexes of polyammonium macrotricyclic ligands with dicarboxylic acids

  • Published:
Journal of the American Society for Mass Spectrometry

Abstract

The host—guest interactions play a very important role in chemical and biological processes. It is therefore important to be able to characterize these complexes. Electrospray mass spectrometry can be used to characterize the complex formation. It provides information on the mass and the charge of these ionic complexes. In this article, we show that the use of ab initio and semiempirical calculations, in addition to the results obtained by electrospray mass spectrometry, reveal to be a promising tool for the study of these noncovalent complexes. In this article, host—guest complexes formed by macropolycyclic polyammonium host molecules and dicarboxylic acids are studied.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Lehn, J.-M. Acc. Chem. Res. 1978, 11, 49.

    Article  CAS  Google Scholar 

  2. Park, C. H.; Simmons, H. E. J. Am. Chem. Soc. 1968, 90, 2431.

    Article  CAS  Google Scholar 

  3. Kotzyba-Hibert, F.; Lehn, J.-M.; Vierling, P. Tetrahedron Lett. 1980, 21, 941.

    Article  CAS  Google Scholar 

  4. Hosseini, M. W.; Lehn, J.-M. J. Am. Chem. Soc. 1982, 3525, 3527.

    Google Scholar 

  5. Kimura, E.; Sakonaka, A.; Yatsunami, T.; Kodama, M. J. Am. Chem. Soc. 1981, 103, 3041.

    Article  CAS  Google Scholar 

  6. Dietrich, B.; Hosseini, M. W.; Lehn, J.-M.; Sessions, R. B. J. Am. Chem. Soc. 1981, 103, 1282.

    Article  CAS  Google Scholar 

  7. Pócsfalvi, G.; Lipták, M.; Huszthy, P.; Bradshaw, J. S.; Izatt, R. M.; Vékey, K. Anal. Chem. 1996, 68, 792.

    Article  Google Scholar 

  8. Sawada, M.; Takai, Y.; Yamada, H.; Hirayama, S.; Kaneda, T.; Tanaka, T.; Kamada, K.; Mizooku, T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe, Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726.

    Article  CAS  Google Scholar 

  9. Vincenti, M. J. Mass Spectrom. 1995, 30, 925.

    Article  CAS  Google Scholar 

  10. Abdoul-Carime, H. J. Chem. Soc. Faraday Trans. 1998, 94, 2407.

    Article  CAS  Google Scholar 

  11. Jaquinot, M.; Leize, E.; Potier, N.; Albrecht, A.-M.; Shanzer, A.; Van Dorsselaer, A. Tetrahedron Lett. 1993, 34, 2771.

    Article  Google Scholar 

  12. Romero, F.; Ziessel, R.; Dupont-Gervais, A.; Van Dorsselaer, A. Chem. Commun. 1996, 551.

  13. Young, D.-S.; Hung, H.-Y.; Liu, L. K. Rapid Commun. Mass Spectrom. 1997, 11, 769.

    Article  CAS  Google Scholar 

  14. Leize, E.; Jaffrezic, A.; Van Dorsselaer, A. J. Mass Spectrom. 1996, 31, 537.

    Article  CAS  Google Scholar 

  15. Wang, K.; Gokel, G. W. J. Org. Chem. 1996, 61, 4693.

    Article  CAS  Google Scholar 

  16. Collette, C.; Meunier, C.; De Pauw, E.; Dumont, A.; Desreux, J. F. Rapid Commun. Mass Spectrom. 1997, 11, 1521.

    Article  CAS  Google Scholar 

  17. Dive, G.; Dehareng, D.; Peeters, D. Int. J. Quantum Chem. 1996, 58, 85.

    Article  CAS  Google Scholar 

  18. Vancampenhout, N.; Dive, G.; Dehareng, D. Int. J. Quantum Chem. 1996, 60, 911.

    Article  CAS  Google Scholar 

  19. McQuarrie, D. A. Statistical Thermodynamics; Harper and Row: New York, 1973.

    Google Scholar 

  20. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F. J. Amer. Chem. Soc. 1985, 107, 3902.

    Article  CAS  Google Scholar 

  21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; and Pople, J. A. Gaussian 94 (Revision D.4), Gaussian Inc., Pittsburgh PA, 1996.

    Google Scholar 

  22. Tatewaki, H.; Huzinaga, S. J. Comp. Chem. 1980, 1, 205.

    Article  CAS  Google Scholar 

  23. Dive, G.; Dehareng, D.; Ghuysen, J. M. Theor. Chim. Acta 1993, 85, 409.

    Article  CAS  Google Scholar 

  24. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.

    Article  CAS  Google Scholar 

  25. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.

    Article  CAS  Google Scholar 

  26. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.

    Article  CAS  Google Scholar 

  27. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.

    Article  CAS  Google Scholar 

  28. Copyright 1993, Biosym Technologies, Inc., 9685 Scranton Road, San Diego, CA 92121-2777, USA.

  29. CFF91 forcefield used by the Discover program from Biosym Technologies, [28]. Results available upon request.

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Spectrométrie de Masse, Département de chimie générale et de chimie physique, Université de Liège, B-4000, Liege, Belgium

    C. Collette, D. Dehareng, E. De Pauw & G. Dive

Authors
  1. C. Collette
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. Dehareng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. De Pauw
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. Dive
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to C. Collette.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Collette, C., Dehareng, D., De Pauw, E. et al. Qualitative comparison between the quantum calculations and electrospray mass spectra o complexes of polyammonium macrotricyclic ligands with dicarboxylic acids. J Am Soc Mass Spectrom 12, 304–316 (2001). https://doi.org/10.1016/S1044-0305(00)00228-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1016/S1044-0305(00)00228-2

Keywords

Search

Navigation