1,2-Proton shifts in pyrazole and related systems: A computational study of [1,5]-sigmatropic migrations of hydrogen and related phenomena

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 11, 1998, Pages 2497-2503

  Alkorta, Ibon ^a   Elguero, José ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000338093     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804086i     Document Type: Article

References (76)

1. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Academic Press, Weinheim, 1970: (a) p. 114; (b) p. 123; (c) p. 126.
2. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Academic Press, Weinheim, 1970: (a) p. 114; (b) p. 123; (c) p. 126.
3. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Academic Press, Weinheim, 1970: (a) p. 114; (b) p. 123; (c) p. 126.
4. N. T. Anh, Les Règles de Woodward-Hoffmann, Ediscience, Paris, 1970; (a) p. 45; (b) p. 51; (c) p. 66.
5. N. T. Anh, Les Règles de Woodward-Hoffmann, Ediscience, Paris, 1970; (a) p. 45; (b) p. 51; (c) p. 66.
6. N. T. Anh, Les Règles de Woodward-Hoffmann, Ediscience, Paris, 1970; (a) p. 45; (b) p. 51; (c) p. 66.
7. T. L. Gilchrist and R. C. Storr, Organic Reactions and Orbital Symmetry, Cambridge University Press, Cambridge, 1972: (a) p. 204; (b) p. 210.
8. T. L. Gilchrist and R. C. Storr, Organic Reactions and Orbital Symmetry, Cambridge University Press, Cambridge, 1972: (a) p. 204; (b) p. 210.
9. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976: (a) p. 98; (b) p. 99.
10. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976: (a) p. 98; (b) p. 99.
11. R. G. Pearson, Symmetry Rules for Chemical Reactions, Wiley, New York, 1976: (a) p. 94; (b) p. 390.
12. R. G. Pearson, Symmetry Rules for Chemical Reactions, Wiley, New York, 1976: (a) p. 94; (b) p. 390.
13. W. J. Hehre, L. Radom, P. von R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986: (a) p. 501; (b) p. 503.
14. W. J. Hehre, L. Radom, P. von R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986: (a) p. 501; (b) p. 503.
15. J. March, Advanced Organic Chemistry (Fourth Edition), Wiley, New York, 1992: (a) p. 1121; (b) p. 1124.
16. J. March, Advanced Organic Chemistry (Fourth Edition), Wiley, New York, 1992: (a) p. 1121; (b) p. 1124.
17. J. Catalán, J. L. G. de Paz, M. Sánchez-Cabezudo and J. Elguero, Bull. Soc. Chim. Fr., 1986, 429.
18. M. W. Wong, R. Leung-Toung and C. Wentrup, J. Am. Chem Soc., 1993, 115, 2465.
19. M. Cao, B. J. Teppen, D. M. Miller, J. Pranata and L. Schäfer, J. Phys. Chem., 1994, 98, 11353.
20. (a) R. Hoffmann and R. B. Woodward, J. Am. Chem. Soc., 1965, 87, 395 and 2511;
21. (b) R. Hoffmann, personal communication.
22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian 94 (Revision D.3), Gaussian, Inc., Pittsburgh, PA, 1995.
23. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
24. A. D. Becke, J. Chem. Phys., 1993, 98, 5648; C. Lee, W. Yang and R. G. Parr, Phys. Rev., 1988, 37, 785.
25. A. D. Becke, J. Chem. Phys., 1993, 98, 5648; C. Lee, W. Yang and R. G. Parr, Phys. Rev., 1988, 37, 785.
26. R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Oxford University, New York, 1990.
27. F. W. Biegler-König, R. F. W. Bader and T. H. J. Tang, J. Comput. Chem., 1982, 3, 317.
28. J. Elguero, C. Marzin, P. Linda and A. R. Katritzky, The Tautomerism of Heterocycles, Academic Press, New York, 1976; J. Elguero, Pyrazoles and their Benzo Derivatives, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 5, p. 167; J. Elguero, Pyrazoles, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. Scriven, Pergamon, Oxford, 1996, vol. 3, p. 1.
29. J. Elguero, C. Marzin, P. Linda and A. R. Katritzky, The Tautomerism of Heterocycles, Academic Press, New York, 1976; J. Elguero, Pyrazoles and their Benzo Derivatives, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 5, p. 167; J. Elguero, Pyrazoles, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. Scriven, Pergamon, Oxford, 1996, vol. 3, p. 1.
30. J. Elguero, C. Marzin, P. Linda and A. R. Katritzky, The Tautomerism of Heterocycles, Academic Press, New York, 1976; J. Elguero, Pyrazoles and their Benzo Derivatives, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 5, p. 167; J. Elguero, Pyrazoles, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. Scriven, Pergamon, Oxford, 1996, vol. 3, p. 1.
31. A. C. Atkinson and A. N. Donev, Optimum Experimental Designs, Oxford Science Publications, Clarendon Press, Oxford, 1992.
32. I. Alkorta, J. Elguero, I. Rozas and A. T. Balaban, THEOCHEM, 1990, 208, 63.
33. J. C. Facelli, THEOCHEM, 1991, 236, 119.
34. W. W. Schoeller and T. Busch, Angew. Chem., Int. Ed. Engl., 1993 32, 617.
35. C. Thomson and C. Glidewell, J. Comput. Chem., 1983, 4, 1.
36. C. Guimon, S. Khayar, F. Gracian, M. Begtrup and G. Pfister-Guillouzo, Chem. Phys., 1989, 138, 157.
37. B. Ya. Simkin, V. I. Minkin and M. N. Glukhovtsev, Adv. Heterocycl. Chem., 1993, 56, 303.
38. M. Alcamí, O. Mó and M. Yáñez, J. Am. Chem. Soc., 1993, 115, 11074.
39. D. H. Magers, E. A. Salter, R. J. Bartlett, C. Salter, B. A. Hess and L. J. Schaad, J. Am. Chem. Soc., 1988, 110, 3435.
40. I. Alkorta, S. Rozas and J. Elguero, Struct. Chem., 1998, 9, 243.
41. J. P. Paolini, J. Comput. Chem., 1990, 11, 1160.
42. F. Jensen, Chem. Phys. Lett., 1989, 161, 368.
43. W. R. Roth, Tetrahedron Lett., 1964, 1009; W. R. Roth and J. König, Liebigs Ann. Chem., 1966, 699, 24; W. R. Roth. Chimia, 1966, 20, 229.
44. W. R. Roth, Tetrahedron Lett., 1964, 1009; W. R. Roth and J. König, Liebigs Ann. Chem., 1966, 699, 24; W. R. Roth. Chimia, 1966, 20, 229.
45. W. R. Roth, Tetrahedron Lett., 1964, 1009; W. R. Roth and J. König, Liebigs Ann. Chem., 1966, 699, 24; W. R. Roth. Chimia, 1966, 20, 229.
46. S. McLean and P. Haynes, Tetrahedron Lett., 1964, 2385.
47. K. Alder and H. J. Ache, Chem. Ber., 1962, 95, 503 and 511.
48. D. S. Glass, R. S. Boikess and S. Weinstein, Tetrahedron Lett., 1966, 999.
49. S. D. Kahn, W. J. Hehre, N. G. Rondan and K. N. Houk, J. Am. Chem. Soc., 1985, 107, 8291.
50. R. V. Stanton and K. M. Merz, J. Chem. Phys., 1994, 100, 434.
51. B. A. Hess and L. J. Schaad, J. Am. Chem. Soc., 1983, 105, 7185.
52. B. A. Hess, L. J. Schaad and J. Pancir, J. Am. Chem. Soc., 1985, 107, 149.
53. F. Jensen and K. N. Houk, J. Am. Chem. Soc., 1987, 109, 3139.
54. Y. P. Liu, G. C. Lynch, T. N. Truong, D. H. Lu, D. G. Truhlar and B. C. Garrett, J. Am. Chem. Soc., 1993, 115, 2408.
55. S. M. Bachrach, J. Org. Chem., 1993, 58, 5414.
56. H. Jiao and P. von R. Schleyer, J. Am. Chem. Soc., 1995, 117, 11529.
57. I. Alkorta, I. Rozas and J. Elguero, Chem. Soc. Rev., 1998, 27, 155.
58. J. D. Dunitz, X-Ray Analysis and the Structure of Organic Molecules, Cornell University Press, Ithaca, 1979, p. 337; H.-B. Burgi and J. D. Dunitz, Structure Correlation, VCH, Weinheim, 1994, vol. 1.
59. J. D. Dunitz, X-Ray Analysis and the Structure of Organic Molecules, Cornell University Press, Ithaca, 1979, p. 337; H.-B. Burgi and J. D. Dunitz, Structure Correlation, VCH, Weinheim, 1994, vol. 1.
60. I. Rozas, I. Alkorta and J. Elguero, J. Phys. Chem., A, 1997, 101, 9457.
61. S. S. C. Ammal, S. P. Ananthavel, P. Venuvanalingam and M. S. Hegde, J. Phys. Chem. A, 1998, 102, 532.
62. Recently, intramolecular hydrogen bonds between N-H and the vertex of pentasubstituted cyclopentadienide anions have been described: G. A. Dushenko, I. E. Mikhailov, O. E. Kompan, A. Zschunke, G. Reck, B. Schulz, C. Mugge and V. I. Minkin, Mendeleev Commun., 1997, 127.
63. M. Ramos, I. Alkorta, J. Elguero, N. S. Golubev, G. S. Denisov, H. Benedict and H. H. Limbach, J. Phys. Chem., A, 1997, 101, 9791.
64. K. Szalewicz and B. Jeziorski, in Molecular Interactions, ed. S. Scheiner, Wiley, Chichester, 1997, p. 4.
65. N. N. Greenwood and A. Earnshaw, Chemistry of the Elements, Pergamon Press, Oxford, 1984, pp. 367-373.
66. G. La Monica and G. A. Ardizzoia, in Progress in Inorganic Chemistry, ed. K. D. Karlin, 1997, 46, 151.
67. J. Elguero, C. Marzin, A. R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, 1976, p. 266.
68. M. L. Roumestant, P. Viallefont, J. Elguero and R. Jacquier, Tetrahedron Lett., 1969, 495.
69. M. T. Chenon, C. Coupry, D. M. Grant and R. J. Pugmire, J. Org. Chem., 1977, 42, 659.
70. R. M. Claramunt, J. Elguero, C. Marzin and J. Seita, Anal. Quim., 1979,75, 701.
71. M. Perrin, A. Thozet, P. Cabildo, R. M. Claramunt, E. Valentí and J. Elguero, Can. J. Chem., 1993, 71, 1443.
72. F. Aguilar-Parrilla, G. Scherer, H. H. Limbach, C. Foces-Foces, F. H. Cano, J. A. S. Smith, C. Toiron and J. Elguero, J. Am. Chem. Soc., 1992, 114, 9657.
73. F. Aguilar-Parrilla, O. Klein, J. Elguero and H. H. Limbach, Ber. Bunsenges. Phys. Chem., 1997, 101, 889.
74. O. Bensaude, M. Chevrier and J. E. Dubois, Tetrahedron, 1978, 34, 2259.
75. J. L. G. de Paz, J. Elguero, C. Foces-Foces, A. L. Llamas-Saiz, F. Aguilar-Parrilla, O. Klein and H. H. Limbach, J. Chem. Soc., Parkin Trans. 2, 1997, 101.
76. R. M. Claramunt, M. D. Santa María, I. Forfar, F. Aguilar-Parrilla, M. Minguet-Bonvehí, O. Klein, H. H. Limbach, C. Foces-Foces, A. L. Llamas-Saiz and J. Elguero, J. Chem. Soc., Perkin Trans. 2, 1997, 1867.