Electronic structure and physicochemical properties of selected penicillins

International Journal of Quantum Chemistry

Volumn 107, Issue 3, 2007, Pages 628-636

  Soriano Correa, Catalina ^a   Sánchez Ruiz, Juan F ^a   Raya, A ^a   Esquivel, Rodolfo O ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b DEPARTAMENTO DE QUÍMICA   (Mexico)

Author keywords

lactam compounds; Ab initio calculations; Electronic structure; Penicillins

Indexed keywords

ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; IONIZATION; MOLECULAR DYNAMICS; PHYSICAL PROPERTIES; PROBABILITY DENSITY FUNCTION;

AB INITIO CALCULATIONS; LACTAM COMPOUNDS; PENICILLINS;

ANTIBIOTICS;

EID: 33846306368     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.21165     Document Type: Article

References (39)

1. Graham, L. P. An Introduction to Medicinal Chemistry; Oxford University Press: New York, 1995.
2. Waxman, D. J.; Strominger, J. L. Annu Rev Biochem 1983, 52, 825.
3. Tipper, D. J.; Strominger, J. L. Proc Natl Acad Sci USA 1965, 54, 1133.
4. Boyd, D. B. In Chemistry and Biology of β-Lactam Antibiotics; Vol 1; Morin, R. B.; German, M., Eds.; Academic Press: New York: 1982, p 437; and references therein.
5. Sandanayaka, V. P.; Prashad, A. S.; Yang, Y.; Williamson, R. T.; Lin, Y. I.; Mansour, T. S. J Med Chem 2003, 46, 2569.
6. Banik, I.; Becker, F. F.; Banik, B. K. J Med Chem 2003, 46, 12.
7. Ghuysen, J. M.; Frére, J. M.; Leygh-Bouille, M.; Coyette, J.; Dusart, J.; Nguyen-Disteche, M. Annu Rev Biochem 1979, 48, 73.
8. Boyd, D. B.; Hermann, R. B.; Presti, D. E.; Marsh, M. M. J Med Chem 1975, 18, 408.
9. Hynn, H. H. Cephalosporins and Penicillins: Chemistry and Biology; Academic Press: New York, 1972.
10. Frau, J.; Donoso, J.; Muñoz, F.; García; B. K. J Mol Struct (Theochem) 1997, 390, 247.
11. Boyd, D. B. J Med Chem 1973, 16, 1195.
12. Boyd, D. B. J Phys Chem 1974, 78, 2604.
13. Boyd, D. B.; Lunn, W. H. W. J Med Chem 1979, 22, 778.
14. Boyd, D. B.; Herron, D. K.; Lunn, W. H. W.; Spitzer, W. A. J Am Chem Soc 1980, 102, 1812.
15. (a) Frau, J.; Coll, M.; Donoso, J.; Muǹoz, F.; García; B. F. J Mol Struct (Theochem) 1991, 231, 109;
16. (b) Zhou, L.; Zhang, Y.; Wu, L; Li, J. J Mol Struct (Theochem) 2000, 497, 137.
17. (a) Frau, J.; Donoso, J.; Muñoz, F.; García; B. F. J Camp Chem 1992, 13, 681;
18. (b) Frau, J.; Donoso, J.; Vilanova, B.; Muñoz, F.; García; B. F. Theor Chim Acta 1993, 86, 229.
19. Frau, J.; Donoso, J.; Muñoz, F.; García; B. F. J Comp Chem 1993, 14, 1545.
20. (a) Álvarez-Idaboy, J. R.; González-Jonte, R.; Hernández-Laguna, A.; Smeyeres, Y. G. J Mol Struct (Theochem) 2000, 504, 13;
21. (b) Bounaim, L.; Smeyeres, N. J.; González-Jonte, R.; Alvarez-ldaboy, J. R.; Ezzamarty, A.; Smeyeres, Y. G. J Mol Struct (Theochem) 2001, 539, 233.
22. Pitarch, J.; Ruíz-López, M. F.; Pascual-Ahuir, J. L.; Silla, F.; Tuñon, I. J Phys Chem B. 1997, 101, 3581.
23. Peña-Gallego, A.; Cabaleiro-Lago, E. M.; Fernández.-Ramos, A.; Hermida-Ramón, J. M.; Martínex-Nuñez, E. J Mol Struct (Theochem) 1999, 491, 177.
24. Massova, T.; Kollman, P. A. J Comp Chem 2002, 23, 1559.
25. Olsen, L.; Rasmussen, T.; Hemmingsen, L.; Ryde, U. J Phys Chem B 2004, 108, 17639.
26. Díaz, N.; Suárez, D.; Sordo, T. L. J Comp Chem 2003, 24, 1864.
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Chccseman, J. R.; Zakrzewski, V. G.; Montgomery Jr., J. A.; Stratmann, R. E.; Buwnt, 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.; Mermucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Peterson, 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.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liasshenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Lnham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Revision A.6; Gaussian: Pittsburgh, PA, 1998.
28. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
29. Politzer, P.; Truhlar, D. G. Chemical Applications of Atomic and Molecular Electrostatic Potentials; Academic Press: New York, 1981.
30. Löwdin, P. O. J Chem Phys 1950, 18, 365.
31. Mölder, U.; Burk, P.; Koppel, I. A. Int J Quantum Chem 2001, 82, 73.
32. (a) Soriano-Correa, C.; Esquivel, O. R.; Sagar, R. P. Int J Quantum Chem 2003, 94, 165.
33. (b) Soriano-Correa, C.; Raya, A.; Sanchez-Ruiz J. F.; Esquivel, O. R. Int T Quantum Chem 2005, 104, 491.
34. Koopmans, T. A. Physica 1933, 1, 104.
35. Parr, R. G.; Szentpály, I. V.; Liu, S. J Am Chem Soc 1999, 121, 1922.
36. Parthasararhi, R.; Subramanian, V.; Roy, D. R.; Chattaraj, P. K. Bioorg Med Chem 2004, 12, 5533.
37. Contreras, R.; Andrés, J.; Domingo, L. R.; Castillo, R.; Perez, P. Tetrahedron 2005, 61, 417.
38. Hardman, J. G.; Limbird, L. E.; Goodman Gilman A. Goodman & Gilman's, The Pharmacological Basis of Therapeutics., 10th ed.; McGraw-Hill: New York, 2001.
39. Michaella, W.; Jamila, F.; Mark, T.; Alison, J. K.; Christopher, M.; Stephen, J. H.; Keith, P. J Am Chem Soc 1997, 119, 9793.