Structural Studies of 1-Aryl-2-aminoimidazolinium Bromides: Focus on Tautomer Preference of the 2-Aminoimidazoline Moiety in the Solid State

• Autorzy: Dobrowolski M. , Cyrański M. , Pisklak M. , Wawer I. , Matosiuk D.
• Języki publikacji: EN

Abstrakty

EN

The crystal structures of five 1-(4-X-phenyl)-2-aminoimidazolinium bromides (where X = -OCH3, -CH3, -H, -Cl and -NO2) were determined by X-ray crystallography with the aim to investigate the tautomer preference of the aminoimidazoline moiety in the solid state. The molecular structures clearly indicate that only the ring nitrogen is protonated. The crystals are stabilized by interactions between the hydrogens of the amino group (also NH fragment of the imidazoline ring) and bromide anion. In the case of the nitro derivative additional strong hydrogen bonds are a consequence of the presence of water molecule in the crystal lattice. The methoxy and nitro derivatives were studied by 15N CP/MAS NMR and the analysis of the tautomer preference was completed by ab initio calculations at the B3LYP/6-311+G** level.

Słowa kluczowe

EN

2-aminoimidazolines; tautomer preference; X-ray diffraction; 15Nsolid state NMR; ab initio calculations

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 5-6
• Strony: 1037--1048
• Opis fizyczny: Bibliogr. 24 poz., rys.

Twórcy

autor

Dobrowolski M.

autor

Cyrański M.

autor

Pisklak M.

autor

Wawer I.

autor

Matosiuk D.

• Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland,

Bibliografia

• 1. Mundla S.R., Wilson L.J., Klopfenstein S.R., Seibel W.L. and Nikolaides N.N., Tetrahedron Lett., 41,6563 (2000).
• 2. a) Wilhelm M. and de Stevens G., Prog. Drug Res., 20, 197 (1976); b) Schier O. and Marxer A., Prog.Drug Res., 25,9 (1981); c) Ruffolo R.R., Rosing E.L. And Waddell J.E., J. Pharmacol. Exp. Then, 209, 429 (1979); d) Weiner N., The Pharmacological Basis of Therapeutics, 6th edn, Gilman A., Goodman L.S. Eds., Macmillan: New York, 1980, p. 183.
• 3. a) Dardonville C. and Rozas L, Med. Res. Rev., 24, 639 (2004); b) Garcia-Sevilla J.A., Escriba P.V. and Guimon J., Ann. NY. Acad. Sci., 881, 392 (1999); c) Bousquet P. and Feldman J., Drugs, 58, 799 (1999);d) Bousquet P, Dontenwill M., Greney H. and Feldman J., J. Cardiovasc. Pharmacol., 35, S21 (2000); e)Bousquet P., Am. J. Hypertens., 13, 84S (2000); f) Bousquet P, Bruban V., Schann S. and Feldman J.,Pharm. Acta. Helv., 74,205 (2000); g) Schann S., Bruban V., Pompermayer K., Feldman J., PfeifTer B.,Renard R, Scalbert E., Bousquet P. and Ehrhardt J.D., J. Med. Chem., 44,1588 (2001); h) Farsang C. And Kapocsi J., Brain. Res. Bull., 49, 317 (1999); i) Hudson A.L. and Lione L.A., Meth. Mol. Biol., 106, 37 (1999); j) Morgan N.G. and Chan S.L., Curr. Pharm. Des., 7, 1413 (2001); k) Nechifor M., Rev. Med.Chir. Soc. Med. Nat. Iasi, 105,438 (2001); 1) Serban D.N., Nechifor M. and Slatineanu S.M., Rev. Med.Chir. Soc. Med. Nat. łasi, 104, 37 (2000); m) Regunathan S. and Reis D.J., Annu. Rev. Pharmacol.ToxicoL, 36,511 (1996); n) Molderings G J., Drugs Fut., 22, 757 (1997).
• 4. a) Servi S., Genc M., Gur S. and Koca M., Eur. J. Med. Chem., 40, 687 (2005); b) Dardonville C., Goya P.,Rozas L., Alsasua A., Martin M.I. and Borrego M., Bioorg. Med. Chem., 8,1567 (2000); c) Saczewski F.,Kobierska E., Debowski T., Charakchiewa-Minol S., Mokrosz M., Gdaniec M. and Nowak E., Arch. Pharm. (Weinheim), 333, 425 (2000); d) Saczewski F., Hudson A.L., Tyacke R.J., Nutt D.J., Mań J.,Tabin P. and Saczewski J., Eur. J. Pharm. Sci., 20, 201 (2003); e) Saczewski F., Debowski T., Petrusewicz J., Gdaniec M., Dąbrowski R.K. and Nowakowska E., Farmaco, 55, 56 (2000).
• 5. Karczmarzyk Z., Matosiuk D., Wysocki W. and Urbańczyk-Lipkowska Z., Analytical Sci. X-Ray Structure Analysis On-Line, 20, x 129 (2004).
• 6. Matosiuk D., Karczmarzyk Z., Krycki A. and Fruziński A., Analytical Sci. X-Ray Structure Analysis On-Line, 21, x19 (2005).
• 7. Matosiuk D., Fidecka S., Antkiewicz-Michaluk L., Dybała I. and Kozioł A.E., Eur. J. Med. Chem., 37,845 (2002).
• 8. Matosiuk D., Pihlaja K., Ovcharenko V., Dybała L, Kozioł A.E., Gdaniec M., Szumiło H. and Karczmarzyk Z., J. Heterocycl. Chem., 40, 93 (2003).
• 9. Matosiuk D., Fidecka S., Antkiewicz-Michaluk L., Lipkowski J., Dybała I. and Kozioł A.E., Eur. J. Med.Chem., 37, 761 (2002).
• 10. Sztanke K., Fidecka S., Kędzierska E., Karczmarzyk Z., Pihlaja K. and Matosiuk D., Eur. J. Med. Chem., 40,127(2005).
• 11. Glennon R.A. and Dukat M., in Bloom F.E., Kupfer D.J. (Eds), Psychopharmacology: Thefourth generation ofprogress, Raven Press, New York, 1995, chapter 37.
• 12. Exner O.,Advances in Linear Free Energy Relationships, Chapman N.B., Shorter J., Eds., Plenum Press: London, 1972.
• 13. Lehmann D.and Faust G.,DDR Pat. 155614; CA. 98, 125599g (1983).
• 14. Knoevenagel E. and Mercklin E., Chem. Ber., 37, 4089 (1904).
• 15. Takeda A., J. Org. Chem., 22, 1096 (1957).
• 16. Oxford Diffraction (2001). CrysAlis CCD and CrysAlis RED. Version l .171.27 p5 beta. Oxford Diffraction Ltd., Wrocław, Poland.
• 17. Sheldrick G.M., Acta Cryst., A46, 467 (1990).
• 18. Sheldrick G.M., SHELXL93. Program for the Refmement ofCrystal Structures, University of Göttingen, Germany.
• 19. International Tables for Crystallography, Ed. A.J.C. Wilson, Kluwer: Dordrecht, 1992, Vol. C.
• 20. Frisch M.J., Trucks G.W., Schlegel H.B., Gili P.M.W., Johnson B.G., Robb M.A., Cheesman J.R., Keith I, Peterson G.A., Montgomery J.A., Raghavachari K., Al-Laham M.A., Zakrzewski V.G., Ortiz J.Y., Foresman J.B., Cioslowski J., Stefanov B.B., Nanayakkara A., Challacombe M., Peng C.Y., AyalaP.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., Gonzales C. and Pople, J.A. Gaussian 98; Gaussian Inc. Pirtsburgh PA, 1998.
• 21. Raczyńska E.D., Cyrański M.K., Gutowski M., Rak J., Gal J.F., Maria PC., Darowska M. and Duczmal K., J. Phys. Org. Chem., 16, 91 (2003).
• 22. Krygowski T.M., Cyrański M.K. and Anulewicz-Ostrowska R., Polish J. Chem., 75, 1939 (2001).
• 23. Luger P, Modern X-ray Analysis on Single Crystals, Walter de Gruyter and Co., Berlin, 1980.
• 24. Webb G.A., Annual Reports on NMR Spectroscopy, l, 18 (1986).