Tytuł artykułu
Autorzy
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
1H, 13C and 15N NMR spectra, supported by the GIAO/DFT calculated (B3LYP/6- 311G//RHF/3-21G) 13C and 15N (B3LYP/6-31++G**//RHF/3-21G) NMR chemical shifts, show that (E)-1,2-di(pyridin-2-yl)ethene-1,2-diol (OO3) is the only tautomer present in chloroform solution. MP2/6-31G**//RHF/6-31G** and MP2/6-31G** ab initio calculations confirm that this perfectly planar form is really more stable than 2-hydroxy-1,2-di(pyridin-2-yl)ethanone (OK1, OK2 and OK3) and other isomeric dimers of pyridine-2-carboxaldehyde. The strong intramolecular hydrogen bonds are responsible for high stability of (E)-1,2-di(pyridin-2-yl)ethene-1,2-diol (the conjugation in the molecule is of minor importance).
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
1411--1417
Opis fizyczny
Bibliogr. 29 poz., rys.
Twórcy
autor
- Department of Chemistry, Technical and Agricultural University, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland
autor
- Department of Chemistry, Technical and Agricultural University, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland
autor
- Department of Chemistry, University of Jyväskylä, P.O. Box 35, FIN-40351 Jyväskylä, Finland
Bibliografia
- 1. Smith M.B. and March J., March’s Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 5th edition, Wiley, NY, 2001, p. 1243.
- 2. Buechler C.A., Addleburg J.W. and Glenn D.M, J. Org. Chem., 20, 1350 (1955).
- 3. Harries C. and Lenart G.H., Liebigs Ann. Chem., 410, 108(1951).
- 4. Crabb T.A., Ingate S.T. and Nevell T.G., J. Chem. Res., M, 2853 (1991).
- 5. Buechler C.A. and Harris Am. Chem. Soc., 72, 5015 (1950).
- 6. Hensel H.R., Angew. Chem., 65,491 (1953). Predominance of (E)-l,2-di(pyridin-2-yl)ethene-l,2-diol..
- 7. Guthrie J.P., in Z. Rappoport (Ed.), The Chemistry of Enols/Thermodynamics of Simple Enols, Wiley, Chichester, 1990, pp. 75-93.
- 8. Hart H., Rappoport Z. and Biali S.E., in Z. Rappoport (Ed.), The Chemistry of Enols/Isolable and Relatively Stable Simple Enols, Wiley: Chichester, 1990, pp. 481-589.
- 9. Gilli G. and Bertolasi V., in Z. Rappoport (Ed.), The Chemistry of Enols/Structural Chemistry, Wiley, Chichester, 1990, pp. 713-764.
- 10. Ranee M., Sorensen O.W., Bodenhausen G., Wagner G., Emst R.R. and Wünthrich K., Biochem. Biophys. Res. Commun., 117,479 (1984).
- 11. Derome A. and Williamson M., J. Magn. Reson., 88, 177 (1990).
- 12. Bax A. and Summers M.F., J. Am. Chem. Soc., 108, 2093 (1986).
- 13. Kolehmainen E., Osmiałowski B., Kiygowski T.M., Kauppinen R., Nissinen M. and Gawinecki R.,.J. Chem. Soc., Perkin Trans. 2, 1259 (2000).
- 14. Kolehmainen E., Osmiałowski B., Nissinen M., Kauppinen R. and Gawinecki R., J. Chem. Soc., Perkin Trans. 2, 2185 (2000).
- 15. Gaussian 98, Revision A.7, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S. and Pople J.A., Gaussian, Inc., Pittsburgh PA, 1998.
- 16. Moll R.B., Poziomek E.J. and Mosher W.A., J. Org. Chem., 36, 1056 (1971).
- 17. Pyridine and Its Derivatives, Part 4, E. Klingsberg (Ed.), Interscience, NY, 1964, p. 140.
- 18. Schaefer J.P. and Bertram J.L.,J. Am. Chem. Soc., 89, 4121 (1967).
- 19.Inoue H., Matsumoto M., Kiyoi S. and Yamanaka M., Bull. Chem. Soc. Jpn., 46, 3900 (1973).
- 20. Weissenfels M., Lippmann E. and Punt J., Z. Chem., 20, 133 (1980).
- 21. Buechler C.A., Chem. Rev., 64, 7 (1964).
- 22. Brown J.N., Jenevein R.M., Stocker J.H. and Trefonas L.M., J. Org. Chem., 37, 3712 (1972).
- 23. Weissenfels M. and Punt J., Z. Chem., 18, 261 (1978).
- 24. Weissenfels M. and Punt J., Tetrahedron, 34, 311 (1978).
- 25. Holubek J. and Volke J., Coll. Czechosl. Chem. Commun., 25, 3292 (I960).
- 26. Ashida T., Hirokawa S. and Okaya Y., Acta Cryst., 18, 122 (1965).
- 27. Osmiałowski B., Kolehmainen E., Nissinen M., Krygowski T.M. and Gawinecki R., J. Org. Chem., 67, 3339 (2002).
- 28. Ośmiałowski B., Kolehmainen E. and Gawinecki R., Magn. Res. Chem., 39, 334 (2001).
- 29. Gilli P., Bertolasi V., Ferretti V. and Gilli G., J. Am. Chem. Soc., 122, 10405 (2000).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0022-0007