Density functional theory study for the cycloaddition of 1,3-butadienes with dimethyl acetylenedicarboxylate. Polar stepwise vs concerted mechanisms

Journal of Physical Chemistry A

Volumn 106, Issue 6, 2002, Pages 952-961

  Domingo, Luis R ^a   Arnó, Manuel ^a   Contreras, Renato ^b   Pérez, Patricia ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY OF CHILE   (Chile)

^c PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY (DFT); ELECTROPHILICITY;

ACETYLENE; ADDITION REACTIONS; BUTADIENE; CHARGE TRANSFER; CHEMICAL BONDS; CONFORMATIONS; DERIVATIVES; REACTION KINETICS; SOLVENTS; SUBSTITUTION REACTIONS;

MOLECULAR DYNAMICS;

EID: 0037074619     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp012603i     Document Type: Article

References (69)

1. Carruthers, W. Some Modern Methods of Organic Synthesis, 2nd ed.; Cambridge University Press: Cambridge, 1978.
2. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
3. Sauer, J. Angew. Chem., Int. Ed. Engl. 1966, 5, 211.
4. Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16.
5. Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
6. Dewar, M.J.S.; Olivella, S.; Stewart, J.J.P. J. Am. Chem. Soc. 1986, 108, 5771.
7. Honk, K.N.; González, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
8. Sakai, S. J. Phys. Chem. A 2000, 104, 922.
9. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98.
10. Woodward, R.B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
11. Loncharich, R.J.; Brown, F.K.; Houk, K.N. J. Org. Chem. 1989, 54, 1129.
12. Houk, K.N.; Loncharich, R.J.; Blake, J.F.; Jorgensan, W.L. J. Am. Chem. Soc. 1989, 111, 9172.
13. Birney, D.M.; Houk, K.N. J. Am. Chem. Soc. 1990, 112, 4127.
14. Jorgensen, W.L.; Dongchul, L.; Blake, J.F. J. Am. Chem. Soc. 1993, 115, 2936.
15. Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12562.
16. Domingo, L.R.; Picher, M.T.; Andrés, J.; Safont; V.S. J. Org. Chem. 1997, 62, 1775.
17. Sustmann, R.; Tappanchai, S.; Bandmann, H. J. Am. Chem. Soc. 1996, 118, 12555.
18. Domingo, L.R.; Jones, R.A.; Picher, M.T. Sepúlveda-Arques, J. Tetrahedron 1995, 51, 8739.
19. Domingo, L.R.; Picher, M.T.; Andrés, J.; Moliner, V.; Safont, V.S. Tetrahedron 1996, 52, 10693.
20. Domingo, L.R.; Picher, M.T.; Zaragozá, R.J. J. Org. Chem. 1998, 63, 9183.
21. Domingo, L.R.; Picher, M.T.; Aurell, M.J. J. Phys. Chem. A 1999, 103, 11425.
22. Domingo, L.R.; Picher, M.T.; Andrés, J. J. Org. Chem. 2000, 65, 3473.
23. Sauer, J.; Wiest, H.; Mielert, A. Chem. Ber. 1964, 97, 3183.
24. Froese, R.D.J.; Coxon, J.M.; West, S.C.; Morokuma, K. J. Org. Chem. 1997, 62, 6991.
25. Abad, A.; Aguló, C.; Castelblanque, L.; Cuñat, A.C.; Navarro, I.; Ramírez de Arellano, M.C. J. Org. Chem. 2000, 65, 4189.
26. Parr, R.G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
27. Parr, R.G.; Pearson, R.G. J. Am. Chem. Soc. 1983, 105, 7512.
28. Pearson, R.G. Chemical Hardness; Applications from Molecules to Solids; Wiley-VHC, Verlag GMBH: Weinheim, Germany, 1997.
29. Parr, R.G.; von Szentpaly, L.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922.
30. Yang, W.; Mortier, W.J. J. Am. Chem. Soc. 1986, 108, 5708.
31. Gázquez, J.L.; Méndez, F. J. Phys. Chem. 1994, 98, 4591.
32. Pérez, P.; Contreras, R. Chem. Phys. Lett. 1998, 292, 239.
33. Contreras, R.; Domingo, L.R.; Andrés, J.; Pérez, P.; Tapia, O. J. Phys. Chem. 1999, 103, 1367.
34. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A., Jr.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Andres, J.L.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian 98, revision A.1; Gaussian, Inc.: Pittsburgh, PA, 1998.
35. Sbai, A.; Branchadell, V.; Oliva, A. J. Org. Chem. 1996, 61, 621.
36. Ziegler, T. Chem. Rev. 1991, 91, 651.
37. Becke, A.D. J. Chem. Phys. 1993, 98, 5648.
38. Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37, 785.
39. Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
40. Stanton, R.V.; Merz, K.M. J. Chem. Phys. 1994, 100, 434.
41. Carpenter, J.E.; Sosa, C.P. THEOCHEM 1994, 311, 325.
42. Goldstein, E.; Beno, B.; Houk, K.N. J. Am. Chem. Soc. 1996, 118, 6036.
43. Sbai, A.; Branchadell, V.; Ortuño, R.M.; Oliva, A. J. Org. Chem. 1997, 62, 3049.
44. Martínez-Merino, V.; Mayoral, J.A.; Salvatella, L. J. Am. Chem. Soc. 1998, 120, 2415.
45. Jursic, B.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1995, 1223.
46. Domingo, L.R.; Arnó, M.; Andrés, J. J. Am. Chem. Soc. 1998, 120, 1617.
47. Schlegel, H.B. J. Comput. Chem. 1982, 3, 214.
48. Schlegel, H.B. Geometry Optimization on Potential Energy Surface. In Modern Electronic Structure Theory; Yarkony, D.R., Ed.; World Scientific Publishing: Singapore, 1994.
49. Scott, A.P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
50. McIver, J.W.J.; Komornicki, A. J. Am. Chem. Soc. 1972, 94, 2625.
51. Fukui, K. J. Phys. Chem. 1970, 74, 4161.
52. González, C.; Schlegel, H.B. J. Phys. Chem. 1990, 94, 5523.
53. González, C.; Schlegel, H.B. J. Chem. Phys. 1991, 95, 5853.
54. Reed, A.E.; Weinstock, R.B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
55. Reed, A.E.; Curtiss, L.A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
56. Kahn, S.D.; Hehre, W.J.; Pople, J.A. J. Am. Chem. Soc. 1987, 109, 1871.
57. Domingo, L.R.; Arnó, M.; Andrés, J. J. Org. Chem. 1999, 64, 5867.
58. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
59. Simkin, B.Y.; Sheikhet, I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach; Ellis Horwood: London, 1995.
60. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
61. Cances, M.T.; Mennunci, V.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
62. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404.
63. Contreras, R.; Fuentealba, P.; Galván, M.; Pérez, P. Chem. Phys. Lett. 1999, 304, 405.
64. Fuentealba, P.; Pérez, P.; Cortreras, R. J. Chem. Phys. 2000, 113, 2544.
65. 23 The lowering of the barrier relative to the reaction with (E)-1,3-pentadiene II is mainly due to the s-cis fused conformation of Cp; the barrier for the cycloaddition between the s-cis conformation of II and DMAD along TSnc-II is 15.2 kcal/mol.
66. Domingo, L.R.; Aurell, M.J.; Pérez, P.; Contreras, R. 2001. Submitted for publication.
67. Wiberg, K.B. Tetrahedron 1968, 24, 1083.
68. For a discussion of the terminology used here, see cite 2 in ref 6.
69. Domingo, L.R. J. Org. Chem. 2001, 66, 3211.