Theoretical (DFT in Vacuo) Studies on the Structure of 2-(_-Aminoethyl)-pyridine - an Agonist of the Histamine H1Receptor. Comparison with Experiment (FT-IR in Apolar Solvent)

• Autorzy: Raczyńska E. , Darowska M. , Rudka T.
• Języki publikacji: EN

Abstrakty

EN

Preliminary quantum-chemical calculations (DFT) were performed for 2-(_-aminoethyl)- pyridine (AEP). In calculations, rotational isomerism around the single C-C and C-N bonds of the chain aminoethyl group in AEPwas considered. Nine stable conformations (four trans and five gauche) with similar Gibbs energies were found. For all of them, vibrational frequencies were calculated at the DFT(B3LYP)/6-31G* level. Infrared (FT-IR) spectra were recorded in apolar solvent (CCl4) for various concentrations of AEP, and compared with those found by computations. The comparison shows that in apolar CCl4 solution AEP exists as a mixture of different conformers. Analysis of the experimental stretching NH and CH vibrations, and the bending in-plane NH vibrations suggests that all nine conformers of AEP can be present in CCl4 solution.

Słowa kluczowe

EN

rotational isomerism; DFT in vacuo

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 11
• Strony: 1529--1546
• Opis fizyczny: Bibliogr. 30 poz., rys.

Twórcy

autor

Raczyńska E.

• Department of Chemistry, Agricultural University, Nowoursynowska 159c, 02-776 Warsaw, Poland

autor

Darowska M.

• Department of Chemistry, Agricultural University, Nowoursynowska 159c, 02-776 Warsaw, Poland

autor

Rudka T.

• Interdisciplinary Department of Biotechnology, Agricultural University, Rakowiecka 26/30, 02-528 Warsaw, Poland

Bibliografia

• 1. Fossati A., Barone D. and Benvenuti C., Pharmacol. Res., 43, 389 (2001).
• 2. a) Tran V.T., Chang R.S.L. and Snyder S.H., Proc. Natl. Acad. Sci. USA, 75, 6290 (1978); b) Eckman D.M., Hopkins N„ McBride C. and Keef K.D., Br. J. Pharmacol., 124, 181 (1998).
• 3. a) Ganellin C.R., In Pharmacology of Histamine Receptors, Ganellin C.R., Parsons M.E. (Eds.), Wright PSG, Bristol, 1982, p. 9; b) Cooper D.G., Vong R.C., Durant G.J. and Ganellin C.R., In Comprehensive Medicinal Chemistry, Jammes P.G., Taylor J.B. (Eds.), Pergamon Press, Oxford, 1990, vol. 3, p. 323.
• 4. Leurs R., Hoffman M., Wieland K. and Timmerman H., Trends Pharmacol. Sci., 21,11 (2000).
• 5. Weinstein H., Chou D., Johnson C.L., Kang S. and Green J.P., Mol. Pharmacol, 12, 738 (1976).
• 6. Weinstein H., Mazurek A.P., Osman R. and Topiol S., Mol. Pharmacol., 29, 28 (1986).
• 7. Karpińska G. and Mazurek A.P., Z. Naturforsch., 50c, 143 (1995).
• 8. Raczyńska E.D., Cyrański M.K., Darowska M. and Rudka T., Targets in Heterocycl. Syst. Chem. Prop., 4, 327 (2000), and references cited therein.
• 9. Raczyńska E.D., Maria P.-C., Gal J.-F. and Decouzon M., J. Phys. Org. Chem., 7, 725 (1994).
• 10. Raczyńska E.D., Rudka T. and Darowska M., J. Mol. Struct. (Theochem), 574, 221 (2001).
• 11. Raczyńska E.D., Darowska M., Rudka T., and Makowski M., J. Phys. Org. Chem., 14, 770 (2001).
• 12. Darowska M. and Raczyńska E.D., Polish J. Chem., 76,1027 (2002).
• 13. Hemandez-Laguna A., Abboud J.-L.M., Notario R., Homan H. and Smeyers Y.G., J. Am. Chem. Soc. 115, 1450(1993).
• 14. Collado J.A., Tuńón I., Silla E. and Ramirez F.J., J. Phys. Chem. A, 104, 2120 (2000).
• 15. Paesen G.C., Adams P.L., Nuttall P.A. and Stuart D.L., Biochim. Biophys. Acta, 1482, 92 (2000).
• 16. a) NCBI (National Center for Biotechnology Information), http://www.ncbi.nlm.nih.gov; b) Proteir Data Bank, http://pdb.ccdc.cam.ac.uk/pdb/.
• 17. Dewar M.J.S., Zoebisch E.G., Healy E.F. and Stewart J.J.P., J. Am. Chem. Soc., 107, 3902 (1985).
• 18. Parr R.G and Yang W., Density Functional Theory of Atoms and Molecules, Oxford University Press NY, 1989.
• 19. a) Becke A.D., J. Chem. Phys., 98,5648 (1993); b) Lee C., Yang W. and Parr R.G., Phys. Rev. B, 37,78 (1988).
• 20. Hehre W.J., Radom L., Schleyer P.v.R. and Popie J.A., Ab Initio Molecular Theory, Wiley, NY, 1986
• 21. Scott A.P and Radom L.,J. Phys. Chem., 100, 16502 (1996).
• 22. Frisch M.J., Trucks G. W., Schlegel H.B., Gill P.M.W., Johnson B.G., Robb M.A., Cheeseman J.R., Keil T.A., Petterson G. A., Montgomery J.A., Raghavachari K., Al-Laham M. A., Zakrzewski V.G., Ortiz J.V., Foresman J.B., Ciosłowski J., Stefanov B., Nanayakkara A., Challacombe M., Peng C.Y., Ayala P. V 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., Pople J. A., Gaussian, Inc., Pittsburgh, PA, 1995.
• 23. Schaftenaar G. and Noordik J.H., J. Comput.-aided Mol. Des., 14, 123 (2000).
• 24. Godfrey P.D. and Brown R.D.,.J. Am. Chem. Soc., 120, 10724 (1998), and references cited therein.
• 25. Krygowski T.M., J. Chem. Inf. Comput. Sci., 33, (1993).
• 26. Krygowski T.M., Cyrański M.K., Czarnocki Z., Hafelinger G. and Katritzky A.R., Tetrahedron, 5 1783 (2000).
• 27. Krygowski M.K. and Cyrański M.K., Chem. Rev., 101, 1385 (2001).
• 28. a) Jamróz M.H., Dobrowolski J.Cz., Rode J.E. and BorowiakM.A., J. Mol. Struct. (Theochem), 618,1( (2002); b) Rode J.E., Dobrowolski J.Cz., Borowiak M.A. and Mazurek A.P., Phys. Chem. Chem. Phy. 4, 3948 (2002).
• 29. Palafox A.M., Int. Quantum Chem., 11, 661 (2000).
• 30. Wojtkowiak B. and Chabanel M., Spectrochimie Moleculaire, Technique et Documentation, Paris, 197