Skip to main content
SpringerLink
Log in

Adduct formed by chromium trioxide and zwitterionic quinolinic acid

  • Invited Paper
  • Published:
Central European Journal of Chemistry

Abstract

Chromium trioxide forms an adduct with zwitterionic quinolinic acid. The structure of the product was found to be (quinolinium-3-carboxylato-O)trioxidochromium(VI), determined by single-crystal X-ray diffraction methods. To evaluate the bonding properties of the compound, its structure was optimized at the B3LYP/6-311G* level of theory. The electronic characteristics were investigated by topological methods applied to the total charge density in various model compounds including the title compound, title compound with a HF molecule presenting a hydrogen bonding and anionic moiety. Calculated aromaticity indices indicate that the quinolinic rings tend to conserve their degree of aromaticity against hydrogen bonding. However, when there is hydrogen bonding involving an N-H bond or when the quinolinium zwitterion is deprotonated, there are clear changes in the interaction between chromium trioxide and the quinolinic moiety.

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. G. Cainelli, G. Cardillo, Chromium Oxidations in Organic Chemistry (Springer-Verlag, Berlin, 1984)

    Google Scholar 

  2. G.P. Haight, D.C. Richardson, N.H. Coburn, Inorg. Chem. 3, 253 (1963)

    Google Scholar 

  3. S.A. Frenneson, J.K. Beattie, G.P. Haight, J. Am. Chem. Soc. 90, 6018 (1968)

    Article  Google Scholar 

  4. (a) V. Amirthalingam, D.F. Grant, A. Senol, Acta Crystallogr. B. 28, 1340 (1972)

    Google Scholar 

  5. M. Dobler, J.D. Dunitz, B. Gubler, H.P. Weber, G. Buchi, J.O. Padilla, Proc. Chem. Soc., London, 383 (1963)

  6. P. Stavropoulos, N. Bryson, M.-T. Youinou, J.A. Osborn, Inorg. Chem. 29, 1807 (1990)

    Article  CAS  Google Scholar 

  7. C. Lopez, A. Gonzalez, F.P. Cossio, C. Palomo, Synth. Commun. 15, 1197 (1985)

    Article  CAS  Google Scholar 

  8. S. Patel, B. K. Mishra, Tetrahedron 63, 4367 (2007)

    Article  CAS  Google Scholar 

  9. D.C. McCain, J. Phys. Chem. 79, 1102 (1975)

    Article  CAS  Google Scholar 

  10. (a) J.K.T. Matikainen, S.A.A. Kaltia, T.A. Hase, M.R. Sundberg, R. Kivekäs, J. Chem. Research (S) 150 (1990)

  11. J.K.T. Matikainen, S.A.A. Kaltia, T.A. Hase, M.R. Sundberg, R. Kivekäs, J. Chem. Research (M), 1117 (1990)

  12. K.V. Gothelf, K.A. Jorgensen, Chem. Rev. 98, 863 (1998)

    Article  CAS  Google Scholar 

  13. T.S. Cameron et al., Can. J. Chem. 81, 612 (2003)

    Article  CAS  Google Scholar 

  14. J. Matikainen, S. Kaltia, T. Hase, P. Kuronen, J. Natur. Prod. 58, 1622 (1995)

    Article  CAS  Google Scholar 

  15. J. Matikainen, S. Kaltia, T. Hase, I. Kilpeläinen, T. Drakenberg, A. Annila, Tetrahedron 49, 8007 (1993)

    Article  CAS  Google Scholar 

  16. J. Matikainen, S. Kaltia, T. Hase, Synth. Commun. 25, 195 (1995)

    Article  CAS  Google Scholar 

  17. (a) M. Torrent, L. Deng, M. Duran, M. Sola, T. Ziegler, Can. J. Chem. 77, 1476 (1999)

    Google Scholar 

  18. T. Ziegler, J. Li, Organometallics 14, 214 (1995)

    Article  CAS  Google Scholar 

  19. A.C.T. North, D.C. Phillips, F.S. Mathews, Acta Cryst. A 24, 467, (1968)

    Article  Google Scholar 

  20. G.M. Sheldrick, Acta Cryst. A 64, 112 (2008)

    Article  Google Scholar 

  21. L.J. Farrugia, J. App. Cryst., 30, 565 (1997)

    Article  CAS  Google Scholar 

  22. M.J. Frisch et al., Gaussian 03, Revision D.02 (Gaussian, Inc., Wallingford CT, 2004)

    Google Scholar 

  23. (a) R.F.W. Bader, Atoms in Molecules: A Quantum Theory (Oxford University Press, New York, 1990)

  24. P.L.A. Popelier, Atoms in Molecules: An Introduction (Pearson Education, Harlow, 2000)

    Google Scholar 

  25. H. Martinez-Garcia, J.A. Dobado, J. Molina, M.R. Sundberg, J. Am. Chem. Soc. 120, 8461 (1998)

    Article  Google Scholar 

  26. P.L.A. Popelier with a contribution from R.G.A. Bone, program MORPHY98 (UMIST: Manchester, England, 1998)

  27. F. Biegler-König, J. Schönbohm, AIM2000, Version 2.0, http://www.aim2000.de

  28. F.W. Biegler-König, R.W.W. Bader, T-H. Tang, J. Comput. Chem. 3, 317 (1982)

    Article  Google Scholar 

  29. S. Noury, X. Krokidis, F. Fuster and B. Silvi, Comput. Chem. 23 (1999) 597

    Article  CAS  Google Scholar 

  30. I. Alkorta, O. Picazo, Arkivoc ix, 305 (2005)

  31. A.L. Spek, Acta Cryst. A 46, 34 (1990); A.L. Spek PLATON — A Multipurpose Crystallographic Tool (Utrecht University, Utrecht, The Netherlands, 2003)

    Google Scholar 

  32. T.M. Krygowski, M.K. Cyranski, Z. Czarnocki, G. Hafelinger, A.R. Katritzky, Tetrahedron 56, 1783 (2000)

    Article  CAS  Google Scholar 

  33. T.M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70 (1993)

    CAS  Google Scholar 

  34. P.R. von Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N.J.R. Hommes, J. Am. Chem. Soc. 118, 6317 (1996)

    Article  CAS  Google Scholar 

  35. P.R. von Schleyer et al., Org. Lett. 3, 2465 (2001)

    Article  CAS  Google Scholar 

  36. K. Woliński, J.F. Hilton, P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990)

    Article  Google Scholar 

  37. http://www.webelements.com

  38. G.B. Deacon, R.J. Phillips, Coord. Chem. Rev. 33, 227 (1980)

    Article  CAS  Google Scholar 

  39. H.L. Krauss, Angew. Chem. 70, 502 (1958)

    Article  CAS  Google Scholar 

  40. X. Fradera, M.A. Austen, R.F. Bader, J. Phys. Chem. A, 103, 304 (1999)

    Article  CAS  Google Scholar 

  41. Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, P.R. von Schleyer, Chem. Rev. 105, 3842 (2005)

    Article  CAS  Google Scholar 

  42. T.M. Krygowski, M.K. Cyranski, Tetrahedron 52, 10255 (1996)

    Article  CAS  Google Scholar 

  43. A.R. Katritzky, K. Jug, D.C. Oniciu, Chem. Rev. 101, 1421 (2001)

    Article  CAS  Google Scholar 

  44. H. Masui, Coord. Chem Rev. 219–221, 957 (2001)

    Article  Google Scholar 

  45. K. Zborowski, L.M. Proniewicz, Pol. J. Chem. 78, 2219 (2004)

    CAS  Google Scholar 

  46. M. Kalinowska, E. Siemieniuk, A. Kostro, W. Lewandowski, J. Mol. Struct. THEOCHEM 761, 129 (2006)

    Article  CAS  Google Scholar 

  47. M.K. Milcic, B.D. Ostojic, S.D. Zaric, Inorg. Chem. 46, 7109 (2007)

    Article  CAS  Google Scholar 

  48. H. Szatylowicz, T.M. Krygowski, Pol. J. Chem. 78, 1719 (2004)

    CAS  Google Scholar 

  49. T.M. Krygowki, H. Szatylowicz, J.E. Zachara, J. Chem. Inf. Comp. Sci. 44, 2077 (2004)

    Google Scholar 

  50. T.M. Krygowski, K. Ejsmont, B.T. Stepien, M.K. Cyranski, J. Poater, M. Sola, J. Org. Chem. 69, 6634 (2004)

    Article  CAS  Google Scholar 

  51. T.M. Krygowski, M.A. Dobrowolski, K. Zborowski, M.K. Cyranski, J. Phys. Org. Chem. 19, 889 (2006)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Laboratory of Inorganic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland

    Markku R. Sundberg & Rolf Å. M. Uggla

  2. Department of Chemistry, Laboratory of Inorganic Chemistry, University of Jyväskylä, PO Box 35, FIN-40351, Jyväskylä, Finland

    Reijo J. Sillanpää

  3. Faculty of Chemistry, Jagiellonian University, 30-060, Kraków, Poland

    Krzysztof K. Zborowski

  4. Department of Chemistry and Industrial Chemistry, University of Pisa, 56126, Pisa, Italy

    Angel Sánchez-González

  5. Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Helsinki, Finland

    Jorma K. T. Matikainen, Seppo A. A. Kaltia & Tapio A. Hase

Authors
  1. Markku R. Sundberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rolf Å. M. Uggla
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reijo J. Sillanpää
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Krzysztof K. Zborowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Angel Sánchez-González
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jorma K. T. Matikainen
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Seppo A. A. Kaltia
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Tapio A. Hase
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Markku R. Sundberg.

Electronic supplementary material

About this article

Cite this article

Sundberg, M.R., Uggla, R.Å.M., Sillanpää, R.J. et al. Adduct formed by chromium trioxide and zwitterionic quinolinic acid. cent.eur.j.chem. 8, 486–493 (2010). https://doi.org/10.2478/s11532-010-0033-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11532-010-0033-z

Keywords

Search

Navigation