Theoretical elucidation on mechanism and reactivity of bisphenol A derivatives as inhibitors and radical scavengers in methacrylate polymerization

Journal of Molecular Structure: THEOCHEM

Volumn 716, Issue 1-3, 2005, Pages 27-31

  Kong, Ling ^a   Wang, Lan Fen ^a   Zhang, Hong Yu ^a  

^a SHANDONG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Bisphenol A derivatives; Bond dissociation enthalpy; Density functional theory; Polymerization; Radical scavenger

Indexed keywords

2,2' BIPHENYLDIOL; 4,4' DIHYDROXYBIPHENYL; 4,4' ISOPROPYLIDENEDIPHENOL; DIETHYLSTILBESTROL; HYDROQUINONE; METHACRYLIC ACID; PHENOL DERIVATIVE; SCAVENGER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; DISSOCIATION; ENTHALPY; POLYMERIZATION; QUANTUM CHEMISTRY; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; THEORETICAL MODEL;

EID: 14644394217     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2004.11.018     Document Type: Article

References (34)

1. G. Moad, and D.H. Solomon The Chemistry of Free Radical Polymerization first ed 1995 Pergamon Press/Elsevier New York/Amsterdam
2. K. Matyjaszewski Controlled radical polymerization Symposium Series 685 1998 American Chemical Society Washington, DC 396 417
3. T. Matsuura, and Y. Ohkatsu Polym. Degrad. Stab. 70 2000 59 63
4. Z.L. Li, J. Cui, X.Y. Hong, Y.C. Liu, and Z.L. Liu J. Phys. Org. Chem. 15 2002 314 318
5. S. Fujisawa, and Y. Kadoma Biomaterials 21 2000 2125 2130
6. M.I. de Heer, H.-G. Korth, and P. Mulder J. Org. Chem. 64 1999 6969 6975
7. H.Y. Zhang Sci. China (Ser B) 42 1999 106 112
8. H.Y. Zhang J. Am. Oil Chem. Soc. 76 1999 745 748
9. H.Y. Zhang Quant. Struct. Act. Relat. 19 2000 50 53
10. J.S. Wright, E.R. Johnson, and G.A. DiLabio J. Am. Chem. Soc. 123 2001 1173 1183
11. H.Y. Zhang, and L.F. Wang J. Mol. Struct. (Theochem) 673 2004 199 202
12. D.A. Pratt, G.A. DiLabio, G. Brigati, G.F. Pedulli, and L. Valgimigli J. Am. Chem. Soc. 123 2001 4625 4626
13. E.G. Bakalbassis, A. Chatzopoulou, V.S. Melissas, M. Tsimidou, M. Tsolaki, and A. Vafiadis Lipids 36 2001 181 190
14. H.Y. Zhang, and L.F. Wang Bioorg. Med. Chem. Lett. 12 2002 225 227
15. Y.M. Sun, H.Y. Zhang, D.Z. Chen, and C.B. Liu Org. Lett. 4 2002 2909 2911
16. H.Y. Zhang, L.F. Wang, and Y.M. Sun Bioorg. Med. Chem. Lett. 13 2003 909 911
17. N. Nenadis, H.Y. Zhang, and M. Tsimidou J. Agric. Food. Chem. 51 2003 1874 1879
18. H.Y. Zhang, Y.M. Sun, and X.L. Wang Chem. Eur. J. 9 2003 502 508
19. G.W. Burton, T. Doba, E.J. Gabe, L. Hughes, F.L. Lee, L. Prasad, and K.U. Ingold J. Am. Chem. Soc. 107 1985 7053 7065
20. M.C. Foti, E.R. Johnson, M.R. Vinqvist, J.S. Wright, L.R.C. Barclay, and K.U. Ingold J. Org. Chem. 67 2002 5190 5196
21. E. Migliavacca, P.A. Carrupt, and B. Testa Helv. Chim. Acta 80 1997 1613 1626
22. H.Y. Zhang J. Am. Oil Chem. Soc. 75 1998 1705 1709
23. L. Kong, Z.L. Sun, L.F. Wang, H.Y. Zhang, and S.D. Yao Helv. Chim. Acta 87 2004 511 515
24. G.A. DiLabio, D.A. Pratt, A.D. LoFaro, and J.S. Wright J. Phys. Chem. A 103 1999 1653 1661
25. G.A. DiLabio, D.A. Pratt, and J.S. Wright Chem. Phys. Lett. 311 1999 215 220
26. G.A. DiLabio, D.A. Pratt, and J.S. Wright J. Org. Chem. 65 2000 2195 2203
27. Y.M. Sun, H.Y. Zhang, and D.Z. Chen Chin. J. Chem. 19 2001 657 661
28. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart J. Am. Chem. Soc. 107 1985 3902 3909
29. J.S. Wright, D.J. Carpenter, D.J. McKay, and K.U. Ingold J. Am. Chem. Soc. 119 1997 4245 4252
30. Y.M. Sun, D.Z. Chen, and C.B. Liu J. Mol. Struct. (Theochem) 618 2002 181 189
31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Jr. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, gaussian 98, Revision A. 11, Gaussian, Inc., Pittsburgh PA, 2001.
32. K. Tanaka, S. Sakai, S. Tomiyama, T. Nishiyama, and F. Yamada Bull. Chem. Soc. Jpn 64 1991 2677 2680
33. S. Tomiyama, S. Sakai, T. Nishiyama, and F. Yamada Bull. Chem. Soc. Jpn 66 1993 299 304
34. Y.M. Sun, and C.B. Liu Eur. J. Org. Chem. 2004 120 128