Modeling the solvent effect on the tacticity in the free radical polymerization of methyl methacrylate

Macromolecules

Volumn 43, Issue 13, 2010, Pages 5602-5610

  Deǧirmenci, Iesa ^a   Eren, Şükrü ^a   Aviyente, Viktorya ^a   De Sterck, Bart ^a   Hemelsoet, Karen ^b,c   Van Speybroeck, Veronique ^b,c   Waroquier, Michel ^b,c  

^a BOGAZICI UNIVERSITY   (Turkey)

^b GHENT UNIVERSITY   (Belgium)

^c QCMM Alliance   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL OXYGEN; DIELECTRIC CONSTANTS; EXPLICIT SOLVENTS; GEOMETRY OPTIMIZATION; H-BONDED; HYDROGEN BONDING INTERACTIONS; IN-VACUUM; ISOTACTICITIES; ISOTACTICS; MMA POLYMERIZATION; MODELING STUDIES; POLARIZABLE CONTINUUM MODEL; PROPAGATION RATE CONSTANT; RADICAL POLYMERIZATION; SMALL SIZE; SOLVENT EFFECTS; SYNDIOTACTICS; TACTICITIES; TRIFLUOROMETHYL;

ACRYLIC MONOMERS; ATOM TRANSFER RADICAL POLYMERIZATION; CARBONYLATION; CONTINUUM MECHANICS; ESTERS; FREE RADICALS; HYDROGEN BONDS; METHANOL; OXYGEN; POLYMERS; RATE CONSTANTS; SOLVENTS; STEREOCHEMISTRY;

FREE RADICAL POLYMERIZATION;

EID: 77955891275     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100608g     Document Type: Article

References (73)

1. Gladysz, J. A. Chem. Rev. 2000, 100, 1167-1168.
2. Sugiyama, Y.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chen. 2006, 44, 2086-2098.
3. (a) Pino, P.; Suter, U. W. Polymer 1976, 17, 977-995.
4. (b) Hatada, K.; Kitayama, T.; Ute, K. Prog. Polym. Sci. 1988, 13, 189-276.
5. (c) Yuki, H.; Hatada, K. Adv. Polym. Sci. 1979, 31, 1-45.
6. Matsumoto, A. In Hndbook of RadicalPolymerization; Matyjaszewski, K., Davis, T. P., Eds.; Wiley-Interscience: Hoboken, NJ, 2002; pp 691-773.
7. (a) Habaue, S.; Okamoto, Y. Chem. Rec. 2001, 1, 46-52.
8. (b) Miura, Y.; Shibata, T.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Am. Chem. Soc. 2006, 128, 16026-16027.
9. Tanaka, H. Prog. Polym. Sci. 1992, 17, 1107-1152.
10. Satoh, K.; Kamigaito, M. Chem Rev. 2009, 109, 5120-5156.
11. Isobe, Y.; Nakano, T.; Okamoto, Y. J. Polym. Sci. Part A: Polym, Chem. 2001, 39, 1463-1471.
12. Isobe, Y.; Fujioka, D.; Habaue, S.; Okamoto, Y. J. Am. Chem. Soc. 2001, 123, 7180-7181.
13. Habaue, S.; Isobe, Y.; Okamoto, Y. Tetrahedron 2002, 58, 8205-8209.
14. Okamoto, Y.; Habaue, S.; Isobe, Y.; Suito, Y. Macromol. Symp. 2003, 195, 75-80.
15. Suito, Y.; Isobe, Y.; Habaue, S.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2496-2500.
16. (a) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605.
17. (b) Isobe, Y; Yamada, K; Nakano, T.; Okamoto, Y Macromolecules 1999, 32, 5979-5981.
18. (c) Isobe, Y; Yamada, K; Nakano, T.; Okamoto, Y J. Polym Sci. Part A: Polym. Chem. 2000, 38, 4693-4703.
19. Miura, Y.; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y.; Kakuchi, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1436-1446.
20. (a) Miura, Y.; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y.; Kakuchi, T. Macromolecules 2005, 38, 1041-1043.
21. (b) Miura, Y; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y; Kakuchi, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1436-1446.
22. Tanaka, H.; Niwa, M. Polymer 2008, 49, 3693-3701.
23. Nakano, T.; Okamoto, Y. In Controlled Radical Polymerization; Matyjazsewski, K, Ed.; ACS Symposium Series 685; American Chemical Society: Washington, DC, 1998; pp 451-462.
24. Beuermann, S. Macromol. Rapid Commun. 2009, 30, 1066-1088.
25. O'Driscoli, K. F.; Monteiro, M. J.; Klumperman, B. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 515-520.
26. Zammit, M. D.; Davis, T. P.; Willett, G. D.; O'Driscoli, K. F. J. Polym. Sci., Part Polym. Chem. 1997, 35, 2311-2321.
27. Harrisson, S.; Barner-Kowollik, C; Davis, T. P.; Evans, K.; Rizzardo, R.; Stenzel, M.; Yin, M. Z. Phys. Chem. 2005, 219, 267-281.
28. Ganachaud, F.; Balic, R.; Monteiro, M. J.; Gilbert, R. G Macromolecules 2000, 33, 8589-8596.
29. Seabrook, S. A.; Tonge, M. P.; Gilbert, R. G. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1357-1368.
30. Frisch, M. J.; Trucks, G W.; Schlegel, H. B.; Scuseria, G E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N; Burant, J. C; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G; Rega, N; Petersson, G A.; Nakatsuji, H; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G; Dapprich, S.; Daniels, A. D.; Strain, M. C; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C; Pople, J. A. Gaussian 03, Revision D.01; Gaussian Inc.: Wallingford, CT, 2004.
31. Smith, D. M.; Nicolaides, A.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1998, 120, 10223-10233.
32. Gonzales, C; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
33. Zhao, Y.; Truhlar, D. G J. Phys. Chem. A 2004, 108, 6908-6918.
34. Furuncuoǧlu, T.; Uǧur, I.; Deǧirmenci, I.; Aviyente, V. Macromolecules 2010, 43, 1823-1835.
35. Liang, K.; Dossi, M.; Moscatelli, D.; Hutchinson, R. A. Macromolecules 2009, 42, 7736-7744.
36. Yu, X.; Pfaendtner, J.; Broadbelt, L. J. J. Phys. Chem. A 2008, 112, 6772-6782.
37. (a) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
38. (b) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
39. (a) Grimme, S.; Steinmetz, M.; Korth, M. J. Chem. Theory Comput. 2007, 3, 42-45.
40. (b) Grimme, S. J. Chem. Phys. 2006, 124, 174301-12.
41. De Sterck, B.; Roel Vaneerdeweg, R.; Du Prez, F.; Waroquier, M; Van Speybroeck, V. Macromolecules 2010, 43, 827-836.
42. Singleton, D. L.; Cvetanovic, R. J. J. Am. Chem. Soc. 1976, 98, 6812-6819.
43. Pilling, M. J.; Seakins, P. W. Reaction Kinetics; Oxford University Press: New York, 1996.
44. Atkins' Physical Chemistry, 8th ed.; Atkins, P., De Paula, J., Eds.; Oxford University Press: New York, 2006.
45. (a) Tomasi, J.; Mennucci, B.; Cancès, E. J. Mol. Struct.: THEO-CHEM 1999, 464, 211-226.
46. (b) Cancès, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041.
47. (c) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158.
48. (d) Mennucci, B.; Cancès, E.; Tomasi, J. J. Phys. Chem. B 1997, 101, 10506-10517.
49. (a) Kelly, C. P.; Cramer, C. J.; Truhlar, D. G J. Phys. Chem. A 2006, 110, 2493-2499.
50. (b) Kamerlin, S. C. L.; Haranczyk, M.; Warshel, A. ChemPhysChem 2009, 10, 1125-1134.
51. (c) De Sterck, B.; Van Speybroeck, V; Mangelinckx, S.; Verniest, G; De Kimpe, N; Waroquier, M. J. Phy. Chem. A 2009, 113, 6375-6380.
52. (d) Van Speybroeck, V; Moonen, K; Hemelsoet, K; Stevens, C; Waroquier, M. J. Am. Chem. Soc. 2006, 128, 8468-8478.
53. (e) Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. J. Chem. Theory Comput. 2005, 1, 1133-1152.
54. (a) Heuts, J. P. A.; Gilbert, R. G.; Radom, L. Macromolecules 1995, 28, 8771-8781.
55. (b) Wong, M. W; Radom, L. J. Phys. Chem. 1995, 99, 8582-8588.
56. (c) Heuts, J. P. A.; Gilbert, R. G; Radom, L. J. Phys. Chem. 1996, 100, 18997-19006.
57. (d) Wong, M. W; Radom, L. J. Phys. Chem. A 1998, 102, 2237-2245.
58. (e) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371.
59. (f) Gómez-Balderas, R.; Coote, M. L.; Henry, D. J.; Fischer, H; Radom, L. J. Phys. Chem. A 2003, 107, 6082-6090.
60. (g) Gómez-Balderas, R.; Coote, M. L.; Henry, D. J.; Radom, L. J. phys. Chem. A 2004, 108, 2874-2883.
61. (h) Henry, D. J.; Coote, M. L.; Gómez-Balderas, R.; Radom, L. J. Am. Chem. Soc. 2004, 126, 1732-1740.
62. Izgorodina, E. I.; Coote, M. L. Chem. Phys. 2006, 324, 96-110.
63. Coote, M. L. Macromol. Theory Simul. 2009, 18, 388-400.
64. Lin, C. Y.; Izgorodina, E. I.; Coote, M. L. Macromolecules 2010, 43, 553-560.
65. Van Cauter, K.; Van Speybroeck, V.; Waroquier, M. Chem-PhysChem 2007, 8, 541-552.
66. (a) Deǧirmenci, İ.; Aviyente, V.; Van Speybroeck, V.; Waroquier, M. Macromolecules 2009, 42, 3033-3041.
67. (b) Deǧirmenci, İ.; Avci, D.; Aviyente, V; Van Cauter, K; Van Speybroeck, V; Waroquier, M. Macromolecules 2007, 40, 9590-9602.
68. (c) Günaydn, H.; Seyhan, S.; Tüzün, N. Ş.; Avci, D.; Aviyente, V Int. J. Quantum Chem. 2005, 103, 176-189.
69. (d) Salman, S.; Ziylan Albayrak, A.; Avci, D.; Aviyente, V J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2574-2583.
70. Kamerlin, S. C. L.; Haranczyk, M.; Warshel, A. ChemPhysChem 2009, 10, 1125-1134.
71. (a) Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646.
72. (b) Bento, A. P.; Bickelhaupt, F. M. J. Org. Chem. 2008, 73, 7290-7299.
73. (c) Catak, S.; Matthias D'hooghe, M.; De Kimpe, N; Waroquier, M.; Van Speybroeck, V. J. Org. Chem. 2010, 75, 885-896.