A density functional theory study of the mechanism of the Paal-Knorr pyrrole synthesis

Journal of Molecular Structure: THEOCHEM

Volumn 811, Issue 1-3, 2007, Pages 97-107

  Mothana, Belquis ^a   Boyd, Russell J ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

B3LYP calculations; Density functional theory; Enamine cyclization; Hemiaminal cyclization; Hydrogen bonding interactions; Onsager and PCM solvent calculations; Paal Knorr reaction; Potential energy surface; Pyrrole formation; Reaction mechanism; Transition state structures

Indexed keywords

EID: 84962349322     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2006.11.034     Document Type: Article

References (32)

1. Jones R.A., and Bean G.P. The Chemistry of Pyrroles (1977), Academic Press, London
2. Paal C. Chem. Ber. 17 (1884) 2756
3. Knorr L. Chem. Ber. 17 (1884) 2863
4. Katritzky A.R., Ostercamp D.L., and Yousaf T.I. Tetrahedron 43 (1987) 5171
5. Amarnath V., Anthony D.C., Amarnath K., Valentine W.M., Wetterau L.A., and Graham D.G. J. Org. Chem. 56 (1991) 6924
6. Amarnath V., Amarnath K., Valentine W.M., Eng M.A., and Graham D.G. Chem. Res. Toxicol. 8 (1995) 234
7. Ogata Y., and Kawasaki A. The Chemistry of the Carbonyl Group (1970), Interscience, London
8. Borsche W., and Fels A. Berichte 39 (1907) 3877
9. Broadbent H.S., Burnham W.S., Losen R.K., and Sheeley R.M. J. Heterocycl. Chem. 5 (1968) 757
10. Sundberg R.J. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry (1984), Pergamon, Oxford 329
11. Kuang-Chih T., Jia-Sheng Y., and Ding-Zhang S. Acta. Chim. Sinica. 39 (1981) 215
12. Kuang-Chih T. Acta. Chim. Sinica. 40 (1982) 720
13. Kuang-Chih T. Acta. Chim. Sinica. 32 (1966) 107
14. Salva A., Donoso J., Frau J., and Munoz F. J. Phys. Chem. A 107 (2003) 9409
15. Frau J., Donoso J., Munoz F., and Garcia Blanco F. J. Comput. Chem. 13 (1992) 681
16. Frau J., Donoso J., Vilanova B., Munoz F., and Garcia Blanco F. Theor. Chim. Acta 86 (1993) 229
17. Weiner S.J., Singh U.C., and Kollman P.A. J. Am. Chem. Soc. 97 (1985) 2219
18. M. J. Frisch et al., Gaussian 03, Revision C.02, Gaussian Inc., Wallingford CT, 2004.
19. Becke A.D. J. Chem. Phys. 98 (1993) 1372
20. Becke A.D. J. Chem. Phys. 98 (1993) 5648
21. Stephens P.J., Devlin F.J., Chabalowski C.F., and Frisch M.J. J. Phys. Chem. 98 (1994) 11623
22. Lee C., Yang W., and Parr R.G. Phys. Rev. B. 37 (1988) 785
23. Onsager L. J. Am. Chem. Soc. 58 (1936) 1486
24. Cossi M., Barone V., Cammi R., and Tomasi J. Chem. Phys. Lett. 255 (1996) 327
25. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151
26. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
27. Miertus S., and Tomasi J. Chem. Phys. 65 (1982) 239
28. Ban F., Lundqvist M.J., Boyd R.J., and Eriksson L.A. J. Am. Chem. Soc. 124 (2002) 2753
29. Galano A., Alvarez-Idaboy J.R., Montero L.A., and Vivier-Bunge A. J. Comput. Chem. 22 (2001) 1138
30. Lynch B.J., and Truhlar D.G. J. Phys. Chem. A. 105 (2001) 2936
31. Durant J.L. Chem. Phys. Lett. 256 (1996) 595
32. Basch H., and Hoz S. J. Phys. Chem. A. 101 (1997) 4416