Toward an understanding of the molecular mechanism of the reaction between 1-methylpyrrole and dimethyl acetylenedicarboxylate. An ab initio study

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9183-9189

  Domingo, L R ^a   Picher, M T ^a   Zaragoza R J ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AMPHOLYTE; DICARBOXYLIC ACID; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICHAELIS CONSTANT; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 0032509454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980036y     Document Type: Article

References (54)

1. For a review, see Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles; Academic Press: NewYork, NY, 1977; pp 146 and 256.
2. Acheson, R. M.; Vernon, J. M. J. Chem. Soc. 1962, 1148.
3. Acheson, R. M.; Vernon, J. M. J. Chem. Soc. 1963, 1008.
4. Lee, C. K.; Hahn, C. S. J. Org. Chem. 1978, 43, 3727.
5. Visnick, M.; Battiste, M. A. J. Chem. Soc., Chem. Commun. 1985, 1621.
6. Houk, K. N.; González, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81 and references therein.
7. (a) Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98.
8. (b) Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
9. (a) Loncharich, R. J.; Brown, F. K.; Houk, K. N. J. Org. Chem. 1989, 54, 1129.
10. (b) Houk, K. N.; Loncharich, R. J.; Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 9172.
11. (c) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
12. (d) Jorgensen, W. L.; Dongchul, L.; Blake, J. F. J. Am. Chem. Soc. 1993, 115, 2936.
13. (e) Sustmann, R.; Tappanchai, S.; Bandmann, H. J. Am. Chem. Soc. 1996, 118, 12555.
14. Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12562.
15. Domingo, L. R.; Picher, M. T.; Andrés, J.; Moliner, V.; Safont, V. S. Tetrahedron 1996, 52, 10693.
16. Domingo, L. R.; Picher, M. T.; Andrés, J.; Safont, V. S. J. Org. Chem. 1997, 62, 1775.
17. Domingo, L. R.; Arnó, M.; Andrés, J. J. Am. Chem. Soc. 1998, 120, 1617.
18. (a) Domingo, L. R.; Jones, R. A.; Picher, M. T. Sepúlveda-Arques, J. Tetrahedron 1995, 51, 8739.
19. (b) Domingo, L. R.; Jones, R. A.; Picher, M. T.; Sepúlveda-Arqués, J. THEOCHEM 1996, 326, 209.
20. (c) Domingo, L. R.; Picher, M. T.; Arnó, M.; Andrés, J.; Safont, V. S. THEOCHEM 1998, 426, 257.
21. Gaussian94, Revision B.1; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1995.
22. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
23. (a) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
24. (b) Schlegel, H. B. Geometry Optimization on Potential Energy Surface, In Modern Electronic Structure Theory, 2 volumes; Yarkony, D. R., Ed.; World Scientific Publishing: Singapore, 1994.
25. McIver, J. W., Jr. Acc. Chem. Res. 1974, 7, 72.
26. (a) Jorgensen, W. L.; Lim, D.; Blake, J. F. J. Am. Chem. Soc. 1993, 115, 2936.
27. (b) Sbai, A.; Branchadell, V.; Oliva, A. J. Org. Chem. 1996, 61, 621.
28. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
29. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
30. (a) Jursic, B.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1995, 1223.
31. (b) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036.
32. (c) Jursic, B. THEOCHEM 1996, 365, 55.
33. B3LYP/6-31G* full optimization of the structures TS2 and IN2 was unsuccessful, giving DFT calculations a very flat PES (see Figure 2). However, DFT restricted optimizations allowed us to obtain accurate energies.
34. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
35. (b) Simkin, B. Ya.; Sheikhet, I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach; Ellis Horwood: London, 1995; pp 78-101.
36. (a) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1990, 112, 4776.
37. (b) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991.
38. (a) Varandas, A. J. C.; Formosinho, S. J. F. J. Chem. Soc., Faraday Trans. 2 1986, 282.
39. (b) Lendvay G. THEOCHEM 1988, 167, 331.
40. (c) Lendvay G. J. Phys. Chem. 1989, 93, 4422.
41. Wiberg, K. B. Tetrahedron 1968, 24, 1083.
42. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
43. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
44. (a) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741.
45. (b) Li, C.-J. Chem. Rev. 1993, 93, 2023.
46. (c) Blokzijl, W.; Engberts, J. B. F. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 1545.
47. (a) Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 7430.
48. (b) Ruiz-López, M. F.; Assfeld, X.; García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1993, 115, 8780.
49. (c) Cativiela, C.; Dillet, V.; García, J. I.; Mayoral, J. A.; Ruiz-López, M. F.; Salvatella, L. THEOCHEM 1995, 331, 37.
50. (a) Jorgensen, W. L.; Lim, D.; Blake, J. F.; Severance, D. L. J. Chem. Soc., Faraday Trans. 1994, 90, 1727.
51. (b) Davidson, M. M.; Hillier, I. H.; Hall, R. J.; Burton, N. A. J. Am. Chem. Soc. 1994, 116, 9294.
52. (c) Cativiela, C.; García, J. I.; Mayoral, J. A.; Salvatella, L. Chem. Soc. Rev. 1996, 25, 209.
53. Bonaccorsi, R.; Cammi, R.; Tomasi, J. J. Comput. Chem. 1991, 12, 301.
54. (b) Tuñón, I.; Silla, E.; Tomasi, J. J. Phys. Chem. 1992, 96, 9043.