(1Z,3Z)-3-[Quinolin-2(1H)-ylidene]-1-(quinolin-2-yl)prop-1-en-2-ol: An unexpected most stable tautomer of 1,3-bis(quinolin-2-yl)acetone

Journal of Molecular Structure

Volumn 930, Issue 1-3, 2009, Pages 78-82

  Gawinecki, Ryszard ^a   Kolehmainen, Erkki ^b   Dobosz, Robert ^a   Ośmiałowski, Borys ^a  

^a UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Ab initio calculations; Benzoannulation; Intramolecular hydrogen bond; NMR; Tautomerism

Indexed keywords

ACETONE; BINDING SITES; COMPLEXATION; HYDROGEN; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AB INITIO CALCULATIONS; BENZOANNULATION; INTRAMOLECULAR HYDROGEN BOND; NMR; TAUTOMERISM;

PROTON TRANSFER;

EID: 84961978563     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.04.041     Document Type: Article

References (22)

1. Elguero J., Marzin C., Katritzky A.R., and Linda P. The Tautomerism of Heterocycles (Adv. Heterocycl. Chem., Supplement 1) (1976), Academic Press, New York
2. Katritzky A.R., and Lagowski J.M. Adv. Heterocycl. Chem. 1 (1963) 339-437
3. Katritzky A.R., Karelson M., and Harris P.A. Heterocycles 32 (1991) 329-369
4. Kolehmainen E., Ośmiałowski B., Nissinen M., Kauppinen R., and Gawinecki R. J. Chem. Soc. Perkin Trans. 2 (2000) 2185-2191
5. Kolehmainen E., Ośmiałowski B., Krygowski T.M., Kauppinen R., Nissinen M., and Gawinecki R. J. Chem. Soc. Perkin Trans. 2 (2000) 1259-1266
6. Ośmiałowski B., Kolehmainen E., Nissinen M., Krygowski T.M., and Gawinecki R. J. Org. Chem. 67 (2002) 3339-3345
7. Ośmiałowski B., Kolehmainen E., and Gawinecki R. Chem. Eur. J. 9 (2003) 2710-2716
8. Bodalski R., Michalski J., and Młotkowska B. Roczniki Chem. 43 (1969) 677-681
9. Newkome G.R., Islam N.B., and Robinson J.M. J. Org. Chem. 40 (1975) 3514-5318
10. Reichardt C., Che D., Heckenkemper G., and Schaefer G. Eur. J. Org. Chem. (2001) 2343-2361
11. Godsi O., Turner B., Suwinska K., Peskin U., and Eichen Y. J. Am. Chem. Soc. 126 (2004) 13519-13525
12. Dobosz R., and Zakrzewska A. J. Mol. Struct.: THEOCHEM 896 (2009) 30-33
13. Braun S., Kalinowski H.-O., and Berger S. 100 and More Basic NMR Experiments - A Practical Course (1995), VCH Publishers, New York
14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Coss, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision D.01, Gaussian, Pittsburgh, PA, 2003.
15. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
16. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
17. Miertus S., and Tomasi J. Chem. Phys. 65 (1982) 239
18. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
19. Ośmiałowski B., Kolehmainen E., and Gawinecki R. Magn. Reson. Chem. 39 (2001) 334-340
20. Van Verth J.E., and Saunders W.H. Can. J. Chem. 77 (1999) 810-816
21. Van Verth J.E., Saunders W.H., and Kermis T.W. Can. J. Chem. 76 (1998) 821-827
22. B. Ośmiałowski, Unpublished results.