NH3-assisted ammonolysis of β-lactams: A theoretical study

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3281-3289

  Díaz, Natalia ^a   Suárez, Dimas ^a   Sordo, Tomás L ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; AMMONIA; AMMONIUM DERIVATIVE; BETA LACTAM ANTIBIOTIC; PENICILLIN G; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG DEGRADATION; DRUG HYDROLYSIS; DRUG STRUCTURE; ENTHALPY; MOLECULAR MODEL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0342675778     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990137b     Document Type: Article

References (39)

1. (a) Page, M. I. Acc. Chem. Res. 1984, 17, 144-151.
2. (b) Page. M. I. The mechanism of Reactions of β-lactams. In The Chemistry of β-lactams; Page, M. I., Ed.; Blackie Academic & Professional: London, 1992; pp 129-147.
3. (a) Nerli, B.; Romanin, D.; Picó, G. Chem.-Biol. Interact. 1997, 104, 179-202.
4. (b) Yvon, M.; Anglade, P.; Val, J. M. FEBS Lett. 1990, 263, 237-240.
5. Yvon, M.; Anglade, P.; Val, J. M. FEBS Lett. 1989, 247, 273-278.
6. Georg, G. I.; Ravikumar, V. T. The Organic Chemistry of β-Lactams; Georg, V. T., Ed.; VCH Publishers: New York, 1993.
7. Yamana, T.; Tsuji, A.; Miyamoto, E.; Mira, E. J. Pharm. Pharmacol. 1975, 27, 56-57.
8. (a) Pitarch, J.; Ruiz-López, M. F.; Silla, E.; Pascual-Ahuir, J. L.; Tuñón, I. J. Am. Chem. Soc. 1998, 120, 2146-2155.
9. (b) Pitarch, J.; Ruiz-López, M. F, Pascual-Ahuir, J. L.; Silla, E.; Tuñón, I. J. Phys. Chem. B. 1997, 101, 3581-3588.
10. Wolfe, S. Can. J. Chem. 1994, 72, 1014-1031.
11. (a) Frau, J.; Donoso, J.; Muñoz, F.; Vilanova, B.; García Blanco, F.; Helv. Chim. Acta 1997, 80, 739-747.
12. (b) Frau, J.; Donoso, J.; Muñoz, F.; García Blanco, F. Helv. Chim. Acta 1966, 89, 353-361.
13. Petrongolo, G.; Ranhgino, R.; Scordamaglia, R. Chem. Phys. 1980, 45, 279-290.
14. (a) Venturini, A.; López-Ortiz, F.; Alvarez, J. M., González, J. J. Am. Chem. Soc. 1998, 120, 1110-1111.
15. (b) Stanton, R. V.; Perakyla, N.; Bakowies, D.; Kollman, P. A. J. Am. Chem. Soc. 1998, 120, 3448-3457.
16. Wladkowsi, B. D.; Chenoweth, S. A.; Sanders, J. N.; Kraus, M.; Stevens, W. J. J. Am. Chem. Soc. 1997, 119, 6423-6431.
17. Díaz, N.; Suárez, D.; Sordo. T. L. Eur. J. Chem., in press.
18. Warshel, A. Computer Modeling of Chemical Reactions in Enzymes and Solutions; John Wiley & Sons: New York, 1991.
19. 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. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
20. Adapted by D. Rinaldi from Rinaldi, D.; Pappalardo, R. R. Quantum Chemistry Program Exchange, program 622; Indiana Uní versity, Bloomington, IN, 1992.
21. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory; John Wiley & Sons Inc.: New York, 1986.
22. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
23. (b) Becke, A. D. Phys. Rev. A. 1988, 38, 3098-3100.
24. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785-789.
25. McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1976.
26. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
27. (b) González, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
28. Curtiss, L. A.; Redfem, P. C. Smith, B. J.; Radom, L. J. Chem. Phys. 1996, 104, 5148.
29. (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.; Kluwer Academic Publishers: Dordrecht, 1991; NATO ASI Series C, Vol. 339, pp 79-92.
30. (b) Dillet, V.; Rinaldi, D.; Angyán, J. G.; Rivail, J. L. Chem. Phys. Lett. 1993, 202, 18.
31. Dillet, V.; Rinaldi, D.; Rivail, J. L. J. Phys. Chem. 1994, 98, 5034-5039.
32. 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.
33. (a) Fujimoto, H.; Kato, S.; Yamabe, S.; Fukui, K. J. Chem. Phys. 1974, 60, 572.
34. (b) Menéndez, M. I.; Sordo, J. A.; Sordo, T. L J. Phys. Chem. 1992, 96, 1185-1187.
35. López, R.; Menéndez, M. I.; Suárez, D.; Sordo, T. L.; Sordo, J. A. Comput. Phys. Commun. 1993, 76, 235-249.
36. MP2/6-31G** and B3LYP/6-31G** levels of theory render a similar structure (N⋯N ≈ 3.2 Å) and interaction energies for the linear ammonia dimer (-4.2 and -4.3 kcal/mol, respectively) in agreement with previous theoretical data: (a) Tao, F.; Klemperer, W. J. Chem. Phys. 1993, 99, 5976-5982.
37. (b) Kieninger, M.; Suhai, S. J. Comput. Chem. 1996, 17, 1508-1519.
38. 3 → 2-azetidinone charge transfer in the syn orientation than in the anti one (see ref 8). This circumstance could have consequences for the placement of catalytic groups in a protein environment.
39. 3-assisted proton transference processes.