Theoretical study of the zwittazido cleavage of 4-azido-2-pyrrolinones: The role of solvent and substituents

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10291-10301

  Suárez, Dimas ^a   Sordo, Tomás L ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; AZIDE;

ARTICLE; CALCULATION; DRUG DEGRADATION; STEREOSPECIFICITY; THEORETICAL STUDY;

EID: 0030668112     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970517j     Document Type: Article

References (48)

1. (a) Moore, H. W.; Goldish, D. M. The chemistry of Halides, Pseudo-Halides and Azides (Supplement D); Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1983; Chapter 8.
2. (b) Moore, H. W. Acc. Chem. Res. 1979, 12, 125-132.
3. (c) Hassner, A. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic Press: New York, 1984; Chapter 2.
4. Hassner, A.; Wiegand, N. H.; Gottlieb, H. E. J. Org. Chem. 1986, 51, 3176-3180.
5. (a) Pacansky, J.; Chang, J. S.; Brown, D. W.; Schwarz, W. J. Org. Chem. 1982, 47, 2233.
6. (b) Moore, H. W.; Hughes, G.; Srinivasachar, K.; Fernández, M.; Nguyen, N.V.; Schoon, D.; Trahne, A. J. Org. Chem. 1985, 50, 4231.
7. Moore, H. W.; Hernández, L.; Kuner, D. M.; Mercer, F.; Sing, A. J. Am. Chem. Soc. 1981, 103, 1769-1777.
8. Georg, G. I.; Ravikumar, V. T. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers, Inc.: New York, 1993.
9. (a) Burke, L. A.; Leroy, G.; Nguyen, M. T.; Sana, M. J. Am. Chem. Soc. 1978, 100, 3668-3674.
10. (b) Bock, H. R.; Dammel, R.; Aygen, S. J. Am. Chem. Soc. 1983, 105, 7681-7685.
11. (c) Yamabe, T.; Kaminoyama, M.; Mintao, T.; Hori, K.; Isomura, K.; Taniguchi, H. Tetrahedron 1984, 40, 2095-2099.
12. Lohr, L. I.; Hanamura, M.; Morokuma, K. J. Am. Chem. Soc. 1983, 105, 5541-5547.
13. (a) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249-6251.
14. (b) Assfeld, X.; Sordo, J. A.; González, J.; Ruiz-López, M. F.; Sordo, T. L. J. Mol. Struct. (Theochem) 1993, 287, 193-199.
15. (c) Assfeld, X.; Ruiz-López, M. F.; González, J.; López, R.; Sordo, J. A.; Sordo, T. L. J. Comput. Chem. 1994, 15, 479-487.
16. (d) López, R.; Sordo, T. L.; Sordo, J. A.; González, J. J. Org. Chem. 1993, 55, 3263-3264.
17. (e) López, R.; Suárez, D.; Ruiz-López, M. F.; González, J.; Sordo, J. A.; Sordo, T. L. J. Chem. Soc., Chem. Commun, 1995, 1677-1678.
18. (e) López, R.; Ruiz-López, M. F.; Rinaldi, D.; Sordo, J. A.; Sordo, T. L. J. Phys. Chem. 1996, 100, 10600-10608.
19. (a) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem Commun. 1993, 450.
20. (b) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995.
21. (c) Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085.
22. (d) Arrieta, A.; Ugalde, J. M.; Cossío, F. P.; Lecea, B. Tetrahedron Lett. 1994, 35, 442.
23. (d) Arrastia, I.; Arrieta, A.; Ugalde, J. M.; Cossío, F. P.; Lecea, B. Tetrahedron Lett. 1994, 35, 7825.
24. (e) Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; López, X.; Arriortua, M. I.; Ugalde, J. M.; Cossío, F. P. J. Org. Chem. 1996, 61, 3070-3079.
25. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Hill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian92, Revision C; Gaussian Inc.: Pittsburgh, PA, 1992.
26. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, P. M. W.; 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.; 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. Gaussian94; Gaussian, Inc.; Pittsburgh, PA, 1995.
27. Adapted by D. Rinaldi from Rinaldi, D.; Pappalardo, R. R. QCPE 1992, 622.
28. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory; John Wiley & Sons Inc.: New York, 1986.
29. Schlegel, H. B. J. Comput. Chem. 1982, 3, 211.
30. Hegarty, D.; Robb, M. A. Mol. Phys. 1979, 38, 1795-1812.
31. McDouall, J. J.; Peasley, K.; Robb, M. A. Chem. Phys. Lett. 1988, 148, 183-189.
32. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
33. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
34. (a) Rivail, J. L.; Rinaldi, D.; Ruiz-López, M. F. In Theoretical and Computational Model for Organic Chemistry, Formosinho, S. J., Csizmadia, I. G., Arnaut, L., Eds.; NATO ASI Series C; Kluwer Academic Publishers: Dordrecht, 1991; Vol. 339, pp 79-92.
35. (b) Dillet, V.; Rinaldi, D.; Angyán, J. G.; Rivail, J. L. Chem. Phys. Lett. 1993, 202, 18.
36. (c) Dillet, V.; Rinaldi, D.; Rivail, J. L. J. Phys. Chem. 1994, 98, 5034-5039.
37. Richards, F. M. Annu. Rev. Biophys. Bioeng. 1977, 6, 151.
38. Claverie, P. In Quantum Theory of Chemical Reactions; Daudel, R., Pullman, A., Salem, L., Veillard, A., Eds.; Reidel, Dordrecht, 1982; Vol. 3, pp 151-175.
39. Ruiz-López, M. F.; Assfeld, X.; García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1993, 115, 8750.
40. To investigate a possible biradical character of this TS, a CAS-MCSCF/6-31G*//MP2/6-31G* single-point calculation was performed using a (8,8) active space of 8 electrons and 6 π/π* and 2 σ/σ* orbitals more directly involved in the bond making and breaking. The HF electronic configuration was observed to clearly dominate the multideterminant expansion of the CAS-MCSCF wave function in which the corresponding coefficient has a value of 0.91. Therefore, nondynamical electronic correlation is expected to play a minor role in this part of the PES.
41. Borden, W. T.; Davidson, E. R. Acc. Chem. Res. 1996, 29, 67-75.
42. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708.
43. Herges, R. Ang. Chem., Int. Ed. Engl. 1994, 33, 255-276.
44. In general, for the nonsubstituted systems studied in this work, the MP2//HF and MP2 relative energies manifest a good agreement. In addition, the solvation energy calculated on gas-phase optimized structures (not detailed here) compare well with that calculated on structures optimized in solution and reported in Table 3.
45. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
46. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
47. Dolbier, W. R.; Koronial, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471-477.
48. 3. These two critical points were confirmed to exist at MP2 level, the resultant barrier being 0.4 kcal/mol.