Hydrogen Bonds in the 1:1 and 2:1 Complexes of Trigonelline with Mineral Acids studied by FTIR, 1H and 13 C NMR Spectroscopies

• Autorzy: Szafran M. , Dega-Szafran Z. , Grunwald-Wyspiańska M. , Barczyński P. , Pankowski M.
• Języki publikacji: EN

Abstrakty

EN

The 1:1 and 2:1 complexes of trigonelline (TRG) with HBr, HI, HNO3, HClO4 and HBF4 have been synthesized and their FTIR, 1H and 13C NMR spectra were analyzed. The 1:1 complexes are divided into two groups. The first group includes complexes with HBr,HI andHNO3, in which a proton is transferred from the acid to TRG and the anions are bonded with the carboxylic group, COOHźźźX- (1). The second comprises complexes with HClO4 and HBF4, with two molecules of protonated TRG forming dimer, like benzoic acid, and the anions interacting exclusively with the positively charged nitrogen atoms (2). All 2:1 complexes crystallized with one water molecule and their FTIR spectra are of Had4i type iii, characterized by an intense broad (continuum) absorption below 1600 cm-1 typical of a short-strong hydrogen bond (SSHB) with a delocalized proton and a single _C=O band. In these complexes the water molecule interacts electrostatically with one positively charged nitrogen atom and the anions with the second one (3). The water molecule additionally forms a hydrogen bond with Br, I and NO3 ions. The proton and carbon chemical shifts of the complexes in D2O have been determined and discussed.

Słowa kluczowe

EN

trigonelline; H-bond complexes; FTIR; 1H and 13C NMR spectra

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 9
• Strony: 1191--1197

Twórcy

autor

Szafran M.

• Faculty of Chemistry, A. Mickiewicz University, ul. Grunwaldzka 6, 60780 Poznań, Poland

autor

Dega-Szafran Z.

• Faculty of Chemistry, A. Mickiewicz University, ul. Grunwaldzka 6, 60780 Poznań, Poland

autor

Grunwald-Wyspiańska M.

• Faculty of Chemistry, A. Mickiewicz University, ul. Grunwaldzka 6, 60780 Poznań, Poland

autor

Barczyński P.

• Faculty of Chemistry, A. Mickiewicz University, ul. Grunwaldzka 6, 60780 Poznań, Poland

autor

Pankowski M.

• Faculty of Chemistry, A. Mickiewicz University, ul. Grunwaldzka 6, 60780 Poznań, Poland

Bibliografia

• 1. Beilstein, 22(1), E III/IV, page 463-4.
• 2. Florkin M„ in Comprehensive Biochemistry, ed. StotzE.H., Elsevier Publ. Comp., Amsterdam, 1965, p. 224
• 3. Robertson A.V. and Marion L., Can. J. Chem., 37, 1043 (1959).
• 4. Knowles W.S. and Elderfield R.C., J. Org. Chem., 7, 389 (1942).
• 5. Cannon J.R., Edmonts J.S,, Francesconi K.A, Raston C .L., Saunders J.B., Skelton B.W. and White A.H., Aust. J. Chem., 34, 787 (1981).
• 6. Dega-Szafran Z., Gdaniec M., Grundwald-Wyspianska M., Kowalczyk I. and Szafran M., J. Mol. Struct., 322, 297 (1994).
• 7. Szafran M., Dega-Szafran Z., Katrusiak A., Buczak G., Gtowiak T., Sitkowski J. and Stefaniak L., J Org. Chem., 63, 2898 (1998).
• 8. Dega-Szafran Z., Katrusiak A. and Szafran M., J. Mol. Struct., 513, 15 (1999).
• 9. Szafran M., Kowalczyk I. and Barczyriski P., Israel. J. Chem., 39, 253 (1999).
• 10. Szafran M., Koput J„ Dega-Szafran Z. and Kwiatkowski J.S., Vibrational Spectrosc., 23,1 (2000).
• 11. Dega-Szafran Z., Dulewicz E. and Szafran M., Magn. Res. Chem., 38,43 (2000).
• 12. Dega-Szafran Z., Katrusiak A. and Szafran M., J. Mol. Struct., 570,165 (2001).
• 13. Szafran M., Koput J., Dega-Szafran Z. and Pankowski M., J. Mol. Struct, (in press).
• 14. Aldrich Library of FT-IR Spectra, Edition II, 1997, Vol. 3.
• 15. Harmon K.M. and Avci G.K., J. Mol. Struct., 117,295 (1984).
• 16. Bratos S., Ratajczak H. and Vlot P., in Hydrogen-Bonded Liquids, eds. Dore J.C. and Teiseire J,, Kluver Academic Publishers, (1991), p. 221, and ref. cited therein.
• 17. Hadii D. and Sheppard N., Proc. Roy. Soc., A216, 247 (1953).
• 18. Hadii D. and Bratos S., in The Hydrogen Bond. Recent Developments in Theory and Experiments, eds. Schuster P., Zundel G. and Sandorfy C., North-Holland, Amsterdam, (1976) Vol. 2, p. 565.
• 19. Hadii D., Obradovic M., Orel B. and Solmayer T., J. Mol. Struct., 14, 439 (1972).
• 20. Luck A.P., in The Hydrogen Bond. Recent Developments in Theory and Experiments, eds. Schuster P., Zundel G. and Sandorfy C., North-Holland, Amsterdam, (1976) Vol. 2, p. 527.
• 21. Unpublished results.
• 22. Chen X-M. and Mak T.C.W., J. Mol. Struct., 221, 265 (1990).