Tautomeric Equilibria in Solutions of 1-Phenacylpyridazin-1-ium and 1-(o-Fluorophenacyl)pyridin-1-ium Cations. DFT and NMR Studies

• Autorzy: Gawinecki R. , Dobosz R. , Ośmiałowski B. , Zakrzewska A.
• Języki publikacji: EN

Abstrakty

EN

Although 1-(2-oxo-2-phenylethyl)pyridazin-1-ium and 1-[2-oxo-2-(o- fluoro phenyl - ethyl)]pyridin-1-ium cations may equilibriate with the respective enol and enaminone tautomeric forms, both experimental NMR data and results of ab in itio calculations show the keto forms to be the only species present in DMSO solution. Intramolecular hydrogen bonds and pi electron delocalization seem to have negligible effect on stabilization of the tautomers. On the other hand, electrostatic repulsions between the onium nitrogen and hydroxy oxygen atoms in the compounds studied are considered to be responsible for the in stability of the enol and enaminone tautomeric forms.

Słowa kluczowe

EN

1-phenacylpyridin-1-ium cation; tautomerism; pi-electron delocalization; ab initio calculations

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 9
• Strony: 1623--1628
• Opis fizyczny: Bibliogr. 17 poz., rys.

Twórcy

autor

Gawinecki R.

autor

Dobosz R.

autor

Ośmiałowski B.

autor

Zakrzewska A.

• Department of Chemistry, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland,

Bibliografia

• l. Ośmialowski B., Janota H. and Gawinecki R., Polish J. Chem., 77, 169 (2003).
• 2.            Carey A.R., O'Ferrall R.A.M. and Murray B.A., J. Chem. Soc. Perkin Trans. 2, 2297 (1993).
• 3.            SzafranM., Szwaj ca A., Leska B., SchroederG. andDega-SzafranZ.,7. Mol. Struct., 643,55 (2002).
• 4.            Zhou J., Hu Yu and Hu H., Heterocycl. Chem., 37, 1165 (2000).
• 5.            Tsuge O., Kanemasa Sh. and Takenaka Sh., Bull. Chem. Soc. Japan, 58, 3137 (1985).
• 6.            Caprosu M., Roman M., Olariu I., Düna St., Mangalagiu I. and Petrovanu M., J. Heterocycl. Chem., 38, 495 (2001).
• 7.            Masaki Y, Otsuka H., Nakayama Y. and Masaharu H., Chem. Pharm. Bull, 21, 2780 (1973).
• 8.            Petrovanu M., Sauciuc A., Gabe I. and Zugravescu I., Rev. Roum. Chim., 14, 1153 (1969).
• 9.            Malkov A.V., Bella M., Starä I.G. and Kocovsky P., Tetrahedron Lett., 42, 3045 (2001).
• 10.          Chapman N.B., Clarke K. and Harvey D.J., J. Chem. Soc, 1202 (1971).
• 11.          Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven T, Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., RegaN., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T, Honda Y, Kitao O., Nakai H., Kiene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C, Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C, Ochterski J.W., Ayala P.Y, Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., 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., WongM.W., Gonzalez C. andPople J.A., Gaussian 03, Revision D.01; Gaussian: Pittsburgh, PA, 2003.
• 12.          Miertus S. and Tomasi J., Chem. Phys., 65, 239 (1982).
• 13.          Miertus S., Scrocco E. and Tomasi J., Chem. Phys., 55, 117 (1981).
• 14.          Gilli G., Bellucci F., Ferretti V. and Bertolasi V., J. Am. Chem. Soc., 111, 1023 (1989).
• 15.          Bertolasi V., Gilli P., Ferretti V. and Gilli G., J. Am. Chem. Soc, 113, 4917 (1991).
• 16.          Gilli P., Bertolasi V., Ferretti V. and Gilli G., J. Am. Chem. Soc, 116, 909 (1994).
• 17.          Bertolasi V., Gilli P., Ferretti V. and Gilli G, Chem. Ew. J., 2, 925 (1996).