DFT studies on tautomeric preferences: Proton transfer in 1,5-bis(pyridin-2-yl)- and 1,5-bis(quinolin-2-yl)pentane-2,4-diones

Journal of Molecular Structure: THEOCHEM

Volumn 940, Issue 1-3, 2010, Pages 119-123

  Dobosz, Robert ^a   Gawinecki, Ryszard ^a  

^a UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

Author keywords

Diketones; Aromaticity; DFT calculations; Intramolecular hydrogen bond; Pyridines; Tautomerism

Indexed keywords

EID: 72049127530     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.10.019     Document Type: Article

References (38)

1. Da{ogonek}browski J., and Kamieńska-Trela K. Spectrochim. Acta 22 (1966) 211-220
2. Da{ogonek}browski J., and Da{ogonek}browska U. Chem. Ber. 101 (1968) 2365-2374
3. Kania L., Kamieńska-Trela K., and Witanowski M. J. Mol. Struct. 102 (1983) 1-17
4. Brown N.M.D., and Nonhebel D.C. Tetrahedron 24 (1968) 5655-5664
5. Da{ogonek}browski J., and Kamieńska-Trela K. J. Am. Chem. Soc. 98 (1976) 2826-2834
6. Czerwiska E., Kozerski L., and Boksa J. Org. Magn. Reson. 8 (1976) 345-349
7. Kozerski L., and Von Philipsborn W. Org. Magn. Reson. 17 (1981) 306-310
8. Kolehmainen E., Ośmiałowski B., Nissinen M., Kauppinen R., and Gawinecki R. J. Chem. Soc. Perkin Trans. 2 (2000) 2185-2191
9. Kolehmainen E., Ośmiałowski B., Krygowski T.M., Kauppinen R., Nissinen M., and Gawinecki R. J. Chem. Soc. Perkin Trans. 2 (2000) 1259-1266
10. Gawinecki R., Kolehmainen E., Loghmani-Khouzani H., Ośmiałowski B., Lovász T., and Rosa P. Eur. J. Org. Chem. (2006) 2817-2824
11. Dobosz R., and Zakrzewska A. J. Mol. Struct. (THEOCHEM) 896 (2009) 30-33
12. Gawinecki R., Kolehmainen E., Dobosz R., and Ośmiałowski B. J. Mol. Struct. 930 (2009) 78-82
13. Srinivasan R., Feenstra J.S., Park S.T., Xu S., and Zewail A.H. J. Am. Chem. Soc. 126 (2004) 2266-2267
14. Dobosz R., Kolehmainen E., Valkonen A., Ośmiałowski B., and Gawinecki R. Tetrahedron 63 (2007) 9172-9178
15. Frisch M.J., et al. Gaussian 03, Revision E.01 (2004), Gaussian, Inc., Wallingford, CT
16. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
17. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
18. Corminboeuf C., Heine T., Seifert G., Schleyer P.v.R., and Weber J. Phys. Chem. Chem. Phys. 6 (2004) 273-276
19. Fallah-Bagher-Shaidaei H., Wannere C.S., Corminboeuf C., Puchta R., and Schleyer P.v.R. Org. Lett. 8 (2006) 863-866
20. Woliński K., Hinton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251-8260
21. Krygowski T.M. J. Chem. Inf. Comput. Sci. 33 (1993) 70-78
22. Sobczyk L., Grabowski J.S., and Krygowski T.M. Chem. Rev. 105 (2005) 3513-3560
23. Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H., and Hommes N.J.R.v.E. J. Am. Chem. Soc. 118 (1996) 6317-6318
24. Cyrański M.K., Ste{ogonek}pień B.T., and Krygowski T.M. Tetrahedron 56 (2000) 9663-9667
25. Palusiak M., and Krygowski T.M. Chem. Eur. J. 13 (2007) 7996-9006
26. Steiner E., Fowler P.W., Soncini A., and Jenneskens L.W. Faraday Discuss. 135 (2007) 309-323
27. Bultinck P. Faraday Discuss. 135 (2007) 347-365
28. Mohajeri A. J. Mol. Struct. (THEOCHEM) 677 (2004) 201-205
29. Ogawa K., and Harada J. J. Mol. Struct. 647 (2003) 211-216
30. Buemi G., Zuccarello F., Venuvanalingam P., and Ramalingam M. Theor. Chem. Acc. 104 (2000) 226-234
31. Rybarczyk-Pirek A., Grabowski S.J., Małecka M., and Nawrot-Modranka J. J. Phys. Chem. A 106 (2002) 11956-11962
32. Gilli G., Bellucci F., Ferretti V., and Bertolasi V. J. Am. Chem. Soc. 111 (1989) 1023-1028
33. Bertolasi V., Gilli P., Ferretti V., and Gilli G. J. Am. Chem. Soc. 113 (1991) 4917-4925
34. Gilli P., Bertolasi V., Ferretti V., and Gilli G. J. Am. Chem. Soc. 116 (1994) 909-915
35. Bertolasi V., Gilli P., Ferretti V., and Gilli G. Chem. Eur. J. 2 (1996) 925-934
36. Clar E. Polycyclic Hydrocarbons vols. 1 and 2 (1964), Academic Press, London
37. Clar E. Aromatic Sextett (1972), Wiley, London
38. Harvey R.G. Polycyclic Aromatic Hydrocarbons (1997), Wiley, New York