The kinetics of addition and fragmentation in reversible addition fragmentation chain transfer polymerization: An ab initio study

Journal of Physical Chemistry A

Volumn 109, Issue 6, 2005, Pages 1230-1239

  Coote, Michelle L ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COMPLEXATION; MOLECULAR DYNAMICS; MONOMERS; NANOSTRUCTURED MATERIALS; OPTIMIZATION; POLYMERIZATION; POLYMERS; POROUS MATERIALS; STYRENE; SUBSTITUTION REACTIONS; THERMODYNAMICS;

AB INITIO CALCULATIONS; CHAIN TRANSFER POLYMERIZATION; RATE COEFFICIENTS; VARIATIONAL TRANSITIONS;

REACTION KINETICS;

EID: 14544273163     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp046131u     Document Type: Article

References (76)

1. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-88.
2. Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615.
3. Chiefari, J.; Chong, Y. K. B.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559-5562.
4. Barner-Kowollik, C.; Dalton, H.; Davis, T. P.; Stenzel, M. H. Angew. Chem., Int. Ed. 2003, 42, 3664-3668.
5. Kowalewski, T.; Tsarevsky, N. V.; Matyjaszewski, K. J. Am. Chem. Soc. 2003, 124, 10632-10633.
6. Chen, M.; Ghiggino, K. P.; Launikonis, A.; Mau, A. W. H.; Rizzardo, E.; Saase, W. H. F.; Thang, S. H.; Wilson, G. J. J. Mater. Chem. 2003, 13, 2696-2700.
7. Sumerlin, B. S.; Lowe, A. B.; Thomas, D. B.; McConnick, C. L. Macromolecules 2003, 36, 5982-5987.
8. Lowe, A. B.; McCormick, C. L. Aust. J. Chem. 2002, 55, 367-379.
9. Delduc, P.; Tailhan, C.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1988, 308.
10. Barner-Kowollik, C.; Quinn, J. F.; Morsley, D. R.; Davis, T. P. J. Polym. Sci., Part A: Polym. Chem. 2001, 59, 1353-1365.
11. Barner-Kowollik, C.; Coote, M. L.; Davis, T. P.; Radom, L.; Vana, P. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2828-2832.
12. Wang, A. R.; Zhu, S.; Kwak, Y.; Goto, A.; Fukuda, T.; Monteiro, M. S. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2833-2839.
13. Kwak, Y.; Goto, A.; Tsuji, Y.; Murata, Y.; Komatsu, K.; Fukuda, T. Macromolecules 2002, 35, 3026-3029.
14. Monteiro, M. J.; de Brouwer, H. Macromolecules 2001, 34, 349-352.
15. Coote, M. L. Aust. J. Chem. 2004, 57, 1125-1132.
16. Coote, M. L.; Radom, L. J. Am. Chem. Soc. 2003, 125, 1490-1491.
17. Coote, M. L. Macromolecules 2004, 37, 5023-5031.
18. Feldermann, A.; Coote, M. L.; Stenzel, M. H.; Davis, T. P.; Barner-Kowollik, C. J. Am. Chem. Soc. 2004, 126, 15915-15923.
19. Goto, A.; Sato, K.; Tsujii, Y.; Fukuda, T.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 2001, 34, 402.
20. Coote, M. L.; Radom, L. Macromolecules 2004, 37, 590-596.
21. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, Wiley: New York, 1986.
22. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, Wiley-VCH: Weinheim, 2000.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, 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.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, 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.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
24. Werner, H.-J.; Knowles, P. J.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Celani, P.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Hampel, C.; Hetzer, G.; Korona, T.; Lindh, R.; Lloyd, A. W.; McNicholas, S. J.; Manby, F. R.; Meyer, W.; Mura, M. E.; Nicklass, A.; Palmieri, P.; Pitzer, R.; Rauhut, G.; Schütz, M.; Stoll, H.; Stone, A. J.; Tarroni, R.; Thorsteinsson, T. MOLPRO 2000.6; University of Birmingham: Birmingham, Alabama, 1999.
25. Henry, D. J.; Sullivan, M. B.; Radom, L. J. Chem. Phys. 2003, 118, 4849-4860.
26. Coote, M. L.; Wood, G. P. F.; Radom, L. J. Phys. Chem. A 2002, 106, 12124-12138.
27. Schwartz, M.; Marshall, P.; Berry, R. J.; Ehlers, C. J.; Petersson, G. A. J. Phys. Chem. A 1998, 102, 10074.
28. See, for example, (a) Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593-1598. (b) Truhlar, D. G.; Garrett, B. C. Acc. Chem. Res. 1980, 13, 440-448. (c) Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Thermodynamics of Organic Compounds; John Wiley & Sons: New York, 1969. (d) Robinson, P. J. J. Chem. Educ. 1978, 55, 509-510. (e) Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, Prentice Hall: Englewood Cliffs, New Jersey, 1989.
29. See, for example, (a) Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593-1598. (b) Truhlar, D. G.; Garrett, B. C. Acc. Chem. Res. 1980, 13, 440-448. (c) Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Thermodynamics of Organic Compounds; John Wiley & Sons: New York, 1969. (d) Robinson, P. J. J. Chem. Educ. 1978, 55, 509-510. (e) Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, Prentice Hall: Englewood Cliffs, New Jersey, 1989.
30. See, for example, (a) Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593-1598. (b) Truhlar, D. G.; Garrett, B. C. Acc. Chem. Res. 1980, 13, 440-448. (c) Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Thermodynamics of Organic Compounds; John Wiley & Sons: New York, 1969. (d) Robinson, P. J. J. Chem. Educ. 1978, 55, 509-510. (e) Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, Prentice Hall: Englewood Cliffs, New Jersey, 1989.
31. See, for example, (a) Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593-1598. (b) Truhlar, D. G.; Garrett, B. C. Acc. Chem. Res. 1980, 13, 440-448. (c) Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Thermodynamics of Organic Compounds; John Wiley & Sons: New York, 1969. (d) Robinson, P. J. J. Chem. Educ. 1978, 55, 509-510. (e) Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, Prentice Hall: Englewood Cliffs, New Jersey, 1989.
32. See, for example, (a) Garrett, B. C.; Truhlar, D. G. J. Chem. Phys. 1979, 70, 1593-1598. (b) Truhlar, D. G.; Garrett, B. C. Acc. Chem. Res. 1980, 13, 440-448. (c) Stull, D. R.; Westrum, E. F., Jr.; Sinke, G. C. The Thermodynamics of Organic Compounds; John Wiley & Sons: New York, 1969. (d) Robinson, P. J. J. Chem. Educ. 1978, 55, 509-510. (e) Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, Prentice Hall: Englewood Cliffs, New Jersey, 1989.
33. These formulas are also summarized in the following: Coote, M. L. Computational Quantum Chemistry for Free-Radical Polymerization. In Encyclopedia of Polymer Science and Technology, 3rd ed.; Kroschwitz, J. I., Ed.; John Wiley and Sons: New York, 2004; Vol. 9, pp 319-371.
34. Bell, R. P. The Tunnel Effect in Chemistry, Chapman and Hall: London, 1980.
35. Truhlar, D. G.; Isaacson, A. D.; Skodje, R. T.; Garrett, B. C. J. Phys. Chem. 1982, 86, 2252.
36. Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1989, 111, 1232.
37. See, for example, Truhlar, D. G.; Garrett, B. C.; Klippenstein, S. J. J. Phys. Chem. 1996, 100, 12771-12800.
38. Eckart, C. Phys. Rev. 1930, 35, 1303.
39. Coote, M. L.; Collins, M. A.; Radom, L. Mol. Phys. 2003, 101, 1329-1338.
40. Van Speybroeck, V.; Van Neck, D.; Waroquier, M.; Wauters, S.; Saeys, M.; Martin, G. B. J. Phys. Chem. A 2000, 104, 10939-10950.
41. Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428-440.
42. Li, J. C. M.; Pitzer, K. S. J. Phys. Chem. 1956, 60, 466-474.
43. East, A. L. L.; Radom, L. J. Chem. Phys. 1997, 106, 6655.
44. (a) Nordholm, S.; Bacskay, G. B. Chem. Phys. Lett. 1976, 42, 253-258.
45. (b) Bacskay, G. B. Unpublished computer program, written in Fortran.
46. Heuts, J. P. A.; Gilbert, R. G.; Radom, L. J. Phys. Chem. 1996, 100, 18997-19006.
47. Heuts, J. P. A.; Gilbert, R. G.; Radom, L. Macromolecules 1995, 28, 8771-8781.
48. Van Speybroeck, V.; Van Neck, D.; Waroquier, M. J. Phys. Chem. A 2002, 106, 8945-8950.
49. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
50. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
51. Baboul, A. G.; Schlegel, H. B. J. Chem. Phys. 1997, 107, 9413.
52. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811-4815.
53. Coote, M. L.; Henry, D. J. Macromolecules 2005, in press.
54. Malick, D. K.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1998, 108, 5704.
55. Chuang, Y. Y.; Corchado, J. C.; Truhlar, D. G. J. Phys. Chem. A 1999, 103, 1140-1149.
56. It should be noted that this spin contamination is, of course, absent in the corresponding ROMP2/6-311+G(3df,2p) calculations. However, the presence of spin contamination at the UHF level is likely to be a symptom of the increased multireference character of the true wavefunction in these delocalized radicals, and the use of a (single-reference) RO-wavefunction in these cases may be enforcing a greater degree of spin localization than would be present in the true wavefunction.
57. Vreven, T.; Morokuma, K. Theor. Chem. Acc. 2003, 109, 125-132.
58. In this previous work, it was found that the forming bond length at the B3-LYP/6-31G(d) level of theory (2.863 Å) was significantly overestimated compared with the higher QCISD/6-31G(d) level (2.579 Å). However, when corrected using the IRCmax technique at the CCSD(T)/ 6-311+G(d,p)//B3-LYP/6- 31G(d) level, a forming bond length of 2.55 Å was obtained.
59. Gómez-Balderas, R.; Coote, M. L.; Henry, D. J.; Radom, L. J. Phys. Chem. A 2004, 108, 2874-2883.
60. Vana, P.; Davis, T. P.; Barner-Kowollik, C. Macromol. Theory Simul. 2002, 11, 823.
61. Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371.
62. 2=CHCl).
63. Henry, D. J.; Coote, M. L.; Gómez-Balderas, R.; Radom, L. J. Am. Chem. Soc. 2004, 126, 1732-1740.
64. Sachchida, N. R.; Truhlar, D. G. J. Chem. Phys. 1983, 79, 6046-6059.
65. Moad, G.; Chiefari, J.; Chong, Y. K.; Krstina, J.; Mayadunne, R. T. A.; Postma, A.; Rizzardo, E.; Thang, S. H. Polym. Int. 2000, 49, 993.
66. Rizzardo, E.; Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Thang, S. H. ACS Symp. Ser. 2000, 786, 278-296.
67. Stenzel, M. H.; Cummins, L.; Roberts, G. E.; Davis, T. P.; Vana, P.; Barner-Kowollik, C. Macromol. Chem. Phys. 2003, 204, 1160-1168.
68. Destarac, M.; Charmot, D.; Franck, X.; Zard, S. Z. Macromol. Rapid Commun. 2000, 21, 1035.
69. Mayadunne, R. T. A.; Rizzardo, E.; Chiefari, J.; Chong, Y. K.; Moad, G.; Thang, S. H. Macromolecules 1999, 52, 6977.
70. Destarac, M.; Taton, D.; Zard, S. Z.; Saleh, T.; Six, I. ACS Symp. Ser. 2003, 854, 536-550.
71. Destarac, M.; Bzducha, W.; Taton, D.; Gauthier-Gillaizeau, I.; Zard, S. Z. Macromol. Rapid Commun. 2002, 25, 1049-1054.
72. Chiefari, J.; Mayadunne, R. T. A.; Moad, C. L.; Moad, G.; Rizzardo, E.; Postma, A.; Skidmore, M. A.; Thang, S. H. Macromolecules 2003, 56, 2273-2283.
73. Adamy, M.; van Herk, A. M.; Destarac, M.; Monteiro, M. I. Macromolecules 2003, 36, 2293-2301.
74. Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750-6756.
75. NBO charges calculated at the B3-LYP/6-311+G(3df,2p)//B3-LYP/ 6-31G(d) level of theory.
76. Barner-Kowollik, C.; Quinn, J. F.; Uyen Nguyen, T. L.; Heuts, J. P. A.; Davis, T. P. Macromolecules 2001, 34, 7849-7857.