Modeling hindered-amine light stabilizer-promoted polymer stabilization: Computational insight into the mechanism for nitroxyl radical regeneration from aminoethers

Journal of the American Chemical Society

Volumn 121, Issue 34, 1999, Pages 7914-7917

  Rossi, Ivan ^a   Venturini, Alessandro ^b   Zedda, Alessandro ^c  

^a MBE   (Italy)

^b CNR   (Italy)

^c CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ETHER DERIVATIVE; METHYLPEROXY RADICAL; NITROXYL RADICAL; POLYETHYLENE; RADICAL; STABILIZING AGENT; TEMPOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENERGY; LIGHT; OXIDATION; REACTION ANALYSIS;

EID: 0033199130     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9906655     Document Type: Article

References (34)

1. Allen, N. S. Chem. Soc. Rev. 1986, 15, 373-404.
2. Shilov, Y. B.; Batalova, R. M.; Denisov, E. T. Dokl. Akad. Nauk, SSSR 1972, 207, 388.
3. Lucarini, M.; Pedulli, G. F. Angew. Makromol. Chem. 1997, 252, 179.
4. (a) Volodarsky, L. B.; Reznikov, V. A.; Ovcharenko, V. I. Synthetic Chemistry of Stable Nitroxides; CRC Press: Boca Raton, FL, 1994; p50.
5. (b) Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629-1632.
6. Bolsman, T. A. B. M.; Blok, A. P.; Frijns, J. H. G. Recl. Trav. Chim. 1978, 97, 313-319.
7. Kavarova-Lerchova, J.; Pilar, J.; Samay, J.; Pospisil, J. Eur. Polym. J. 1978, 14, 601-604.
8. Grattan, D. W.; Carlsson, D. J.; Wiles, D. M. Polym. Degrad. Stab. 1979, 1, 69.
9. For a review on the subject, see: Gugumus F. Polym.Degrad. Stab. 1993, 40, 167-215.
10. (a) Klemchuk, P. P.; Gande, M. E.; Cordola, E. Polym. Degrad. Stab. 1990, 27, 65.
11. (b) Step, E. N.; Turro, N. J.; Klemchuk, P. P.; Gande, M. E. Angew. Makromol. Chem. 1995, 232, 65-83.
12. Kysel, O.; Mach, P.; Micov, M. Polym. Degrad. Stab. 1993, 40, 31-35.
13. (a) Becke A. D. J. Chem. Phys. 1998, 98, 5648-5652.
14. (b) Becke A. D. Phys. Rev. A 1988, 38, 3098-3100. Lee C.; Yang W.; Parr R. G. Phys. Rev. B 1988, 37, 785-789.
15. (b) Becke A. D. Phys. Rev. A 1988, 38, 3098-3100. Lee C.; Yang W.; Parr R. G. Phys. Rev. B 1988, 37, 785-789.
16. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
17. (a) Hehre, W. J.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1969, 51, 2657-2664.
18. (b) Hehre, W. J.; Ditchfield, R.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1970, 52, 2769-2773.
19. (a) Humbel, S.; Sieber, S.; Morokuma, K. J. Chem. Phys. 1996, 105, 1959-1967.
20. (b) Svensson, M.; Humbel, S.; Morokuma, K. J. Chem. Phys. 1996, 105, 3654-3661.
21. (a) Coitiño, E. L.; Truhlar, D. G.; Morokuma, K. Chem. Phys. Lett. 1996, 259, 159-164.
22. (b) Noland, M.; Coitiño, E. L.; Truhlar, D. G. J. Phys. Chem. A 1997, 101, 1193-1197.
23. (c) Corchado, J. C.; Truhlar, D. G. J. Phys. Chem. A 1998, 102, 1895-1898.
24. Svensson, M.; Humbel, S.; Froese, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1996, 100, 19357-19363.
25. (a) Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519.
26. (b) Halgren, T. A. J. Comput. Chem. 1996, 17, 520-552.
27. (c) Halgren, T. A. J. Comput. Chem. 1996, 17, 553-586.
28. (d) Halgren, T. A. J. Comput. Chem. 1996, 17, 587-615.
29. (e) Halgren, T. A. J. Comput. Chem. 1996, 17, 616-641.
30. Spartan version 5.0; Wavefunction, Inc., Irvine, CA, 1998.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; 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.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; 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. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
32. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368.
33. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
34. (c) Melissas, V. S.; Truhlar, D. G.; Garrett, B. C. J. Chem. Phys. 1992, 96, 5758-5772.