Creatinine and Creatininium Cation in Water Solution. Tautomerism and Quantitative Interpretation of the Solution Acidity Effect on 1H, 13C and 14 N NMR Chemical Shifts

• Autorzy: Kotsyubynskyy D. , Molchanov S. , Gryff-Keller A.
• Języki publikacji: EN

Abstrakty

EN

1H, 13C and 14N NMR chemical shifts for creatinine in water solutions of various acidity have been measured. Analysis of these data enabled determination of the acidity constant of creatininium cation and the chemical shifts of the neutral and protonated forms of creatinine. Molecular energies and carbon and nitrogen magnetic shielding constants for various tautomeric structures of the investigated species have been calculated using the quantum chemistry method GIAO DFT B3LYP/6-311++G(2d,p). Compilation of the available experimental and theoretical results has provided additional information on the problem of tautomerism of this important biological molecule.

Słowa kluczowe

EN

creatinine; protonation; tautomerism; 1H; 13C; 14N NMR; chemical shift calculations GIAO DFT

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 2
• Strony: 239--248
• Opis fizyczny: Bibliogr. 22 poz., rys.

Twórcy

autor

Kotsyubynskyy D.

• Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland

autor

Molchanov S.

• Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland

autor

Gryff-Keller A.

• Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland

Bibliografia

• 1. Harper H.A., Rodwell V.W. and Mayes P.A., in Zarys Chemii Fizjologicznej, Paristwowy Zaklad Wydawnictw Lekarskich, Warszawa (1983) p. 612, (in Polish); Harper H.A., Rodwell V.W. and Mayes P.A., in Review of Physiological Chemistry, Ed. Drawer L., Lange Medical Publications, Los Altos, California, 1979.
• 2. Blau N., Duran M. and Blaskovics M., Physician’s Guide to the Laboratory Diagnosis of Metabolic Diseases, ed. Chapman and Hall Medical, London 1996.
• 3. Reddick R.E. and Kenyon G.L., J. Am. Chem. Soc., 109, 4380 (1987).
• 4. Butler A.R. and Glidewell C., J. Chem. Soc. Perkin Trans. 2,1465 (1985).
• 5. Olofson A., Yakushijin K. and Home D.A., J. Org. Chem., 63, 5787 (1998).
• 6. Smith R.L., Cochran D.W., Gund P. and Cragoe E.J., Jr., J. Am. Chem. Soc., 101,191 (1979).
• 7. Richards R.E. and Thomas N.A., J. Chem. Soc. Perkin Trans. 2, 4, 368, (1974).
• 8. Dietrich R.F., Marietta M.A. and Kenyon G.L., Org. Magn. Reson., 13, 79 (1980).
• 9. Kenyon G.L. and Rowley G.L., J. Am. Chem. Soc., 93, 5552 (1971).
• 10. Craw J.S., Greatbanks S.P. and Hillier I.H., J. Chem. Phys., 106, 16, (1997).
• 11. Grzybowski A.K. and Datta S.P., J. Chem. Soc., 187 (1964).
• 12. du Pre S. and Mendel H,,Acta Cryst., 8, 311 (1955).
• 13. Bell T.W., Hou Z., Lou Y., Drew M.G.B., Chapoteau E., Czech B.P. and Kumar A., Science, 269, 671 (1995).
• 14. Matsumoto K. and Rapoport H., J. Org. Chem., 33, 552, (1968).
• 15. Srinivasan R. and Stewart R., Can. J. Chem., S3, 224 (1975).
• 16. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Jr., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K, Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S. and Pople J.A., 1998, Gaussian98, Revision A.8, Gaussian, Inc., Pittsburgh PA.
• 17. Cheeseman J.R., Trucks G., Keith T.A. and Frisch M.J., J. Chem. Phys., 104, 5497 (1996).
• 18. Witanowski M., Sicinska W., Biedrzycka Z. and Webb G.A., J. Mol. Struct., 380,133 (1996).
• 19. Englander S.W., in Encyclopedia of Nuclear Magnetic Resonance, edited by Grant D.M. and Harris R.K., John Wiley & Sons, Chichester, NY, Vol. 4,2415 (1996).
• 20. Dempsey C.E., Prog. Nucl. Magn. Resort. Spectrosc., 39, 135 (2001).
• 21. Bamforth F.J., Dorian V., Vallance H. and Wishart D.S., J. Inherited Metab. Dis., 22, 297 (1999).
• 22. Moolenaar S.H., Engelke U.F.H., Hoenderop S.M.G.C., Sewell A.C., Wagner L. and Wevers R.A., Handbook of'H-NMR Spectroscopy in Inborn Errors of Metabolism, SPS Publications, Heilbronn