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Abstrakty
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.
Wydawca
Czasopismo
Rocznik
Tom
Strony
1623--1628
Opis fizyczny
Bibliogr. 17 poz., rys.
Twórcy
autor
autor
autor
autor
- Department of Chemistry, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland, gawiner@utp.edu.pl
Bibliografia
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- 3. SzafranM., Szwaj ca A., Leska B., SchroederG. andDega-SzafranZ.,7. Mol. Struct., 643,55 (2002).
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- 6. Caprosu M., Roman M., Olariu I., Düna St., Mangalagiu I. and Petrovanu M., J. Heterocycl. Chem., 38, 495 (2001).
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- 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).
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- 17. Bertolasi V., Gilli P., Ferretti V. and Gilli G, Chem. Ew. J., 2, 925 (1996).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ7-0015-0071