Stability of the dimers of Aza analogs of 2-formylpyrrole. Conjugation versus hydrogen bonding

Heterocyclic Communications

Volumn 9, Issue 3, 2003, Pages 275-280

  Gawinecki, Ryszard ^a   Ośmiałowski, Borys ^a   Kolehmainen, Erkki ^b   Janota, Henryk ^a  

^a UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

2 FORMYLPYRROLE; ALDEHYDE DERIVATIVE; PYRAZINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CONJUGATION; DIMERIZATION; ENERGY; HYDROGEN BOND; MOLECULE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84962468669     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2003.9.3.275     Document Type: Article

References (19)

1. E. Galeazzi, A. Gusmán, J.L. Nava, Y. Liu, M.L. Maddox and J. M. Muchowski, J. Org. Chem., 60, 1090 (1995).
2. B. Kaptein, R.M. Kellogg and F. van Bolhuis, Recl. Trav. Chim., 109, 388 (1990).
3. J.-W. Kim, S.M. Abdelaal, L. Bauer and N.E. Heimer, J. Heterocycl. Chem., 32, 611 (1995).
4. K. L. Kirk, J. Org. Chem., 43, 4381 (1978).
5. H. McNab, J. Chem. Soc., Perkin Trans. 1, 653 (1987).
6. H. R. Hensel, Chem. Ber., 98, 1325 (1965).
7. E. J. Browne, Aust. J. Chem., 24, 393 (1971).
8. C. Wijnberger and C. L. Habraken, J. Heterocycl. Chem., 6, 545 (1969).
9. Yu.A. Zhdanov and G.N. Dorofeenko, Zh. Obshch. Khim., 29, 2677 (1959).
10. A. Bax, R.H. Griffey and B.L. Hawkins, J. Magn. Reson., 55, 301 (1983).
11. A. Bax and S. Subramanian, J. Magn. Reson., 67, 565 (1986).
12. A. Bax and M.F. Summers, J. Am. Chem. Soc., 108, 2093 (1986).
13. B. Ośmiałowski, E. Kolehmainen, M. Nissinen, T.M. Krygowski and R. Gawinecki, J. Org. Chem., 67, 3339 (2002).
14. Gaussian 98, Revision A.7, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle and J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
15. S. Miertus and J. Tomasi, Chem. Phys., 65, 239 (1982).
16. S. Miertus, E. Scrocco and J. Tomasi, Chem. Phys., 55, 117 (1981).
17. A.F. Hegarty and P. O'Neil, in Z. Rappoport (Ed.), The Chemistry of Functional Groups, Enols of Carboxykic Acids and Esters in The Chemistry of Enols, Wiley, Chichester, 1990, pp. 639-650.
18. P. Gilli, V. Bertolasi, V. Ferretti and G. Gilli, J. Am. Chem. Soc., 122, 10405 (2000).
19. I. Yavari, Sh. Moradi, H.K. Fard, F. Nourmohammadian and D. Tahmassebi, Journal of Molecular Structure (Theochem), 578, 249 (2002).