Determination of Arrhenius parameters for propagation in free-radical polymerizations: An assessment of ab initio procedures

Journal of Physical Chemistry

Volumn 100, Issue 49, 1996, Pages 18997-19006

  Heuts, Johan P A ^a,b,c   Gilbert, Robert G ^b   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748388297     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9614097     Document Type: Article

References (102)

1. For recent experimental studies on radical addition reactions, see: (a) Citterio, A.; Sebastiano, R.; Marion, R.; Santi, R. J. Org. Chem. 1991, 56, 5328.
2. (b) Héberger, K.; Walbiner, M.; Fischer, H. Angew Chem., Int. Ed. Engl. 1992, 31, 635.
3. (c) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R.; Pan, H.-Q. J. Am. Chem. Soc. 1993, 115, 1577.
4. (d) Héberger, K.; Fischer, H. Int. J. Chem. Kinet. 1993, 25, 249.
5. (e) Héberger, K.; Fischer, H. Int. J. Chem. Kinet. 1993, 25, 913.
6. (f) Wu, J. Q.; Beranek, I.; Fischer, H. Helv. Chim. Acta 1995, 78, 194.
7. (g) Héberger, K.; Lopata, A. J. Chem. Soc., Perkin Trans. 2 1995, 91.
8. (g) Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1996, 118, 437.
9. (h) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R.; Pan, H.-Q. J. Org. Chem. 1996, 61, 2027.
10. For recent experimental studies on propagation rate coefficients, see: (a) Davis, T. P.; O'Driscoll, K. F.; Piton, M. C.; Winnik, M. A. Macromolecules 1990, 23, 2113.
11. (b) Davis, T. P.; O'Driscoll, K. F.; Piton, M. C.; Winnik, M. A. Polym. Int. 1991, 24, 65.
12. (c) Deibert, S.; Bandermann, F.; Schweer, J.; Sarnecki, J. Makromol. Chem., Rapid Commun. 1992, 13, 351.
13. (d) Pascal, P.; Winnik, M. A.; Napper, D. H.; Gilbert, R. G. Makromol. Chem., Rapid Commun. 1993, 14, 213.
14. (e) Hutchinson, R. A.; Aronson, M. T.; Richards, J. R. Macromolecules 1993, 26, 6410.
15. (f) Schoonbrood, H. A. S.; Van den Reijen, B.; De Kock, J. B. L.; Manders, B. G.; Van Herk, A. M.; German, A. L. Macromol. Rapid Commun. 1995, 16, 119.
16. (g) Bergert, U.; Buback, M.; Heyne, J. Macromol. Rapid Commun. 1995, 16, 275.
17. (h) Bergert, U.; Beuermann, S.; Buback, M.; Kurz, C. H.; Russell, G. T.; Schmaltz, C. Macromol. Rapid Commun. 1995, 16, 425.
18. (i) Shipp, D. A.; Smith, T. A.; Solomon, D.; Moad, G. Macromol. Rapid Commun. 1995, 16, 837.
19. (j) Buback, M.; Gilbert, R. G.; Hutchinson, R. A.; Klumperman, B.; Kuchta, F.-D.; Manders, B. G.; O'Driscoll, K. F.; Russell, G. T.; Schweer, J. Macromol. Chem. Phys. 1995, 196, 3267.
20. (k) Lyons, R. A.; Hutovic, J.; Piton, M. C.; Christie, D. I.; Clay, P. A.; Manders, B. G.; Kable, S. H.; Gilbert, R. G. Macromolecules 1996, 29, 1918.
21. For recent theoretical studies on the addition of substituted alkyl radicals to alkenes, see: (a) Houk, K. N.; Paddon-Row, M. N.; Spellmeyer, D. C.; Rondan, N. G.; Nagase, S. J. Org. Chem. 1986, 51, 2874.
22. (b) Arnaud, R.; Subra, R.; Barone, V.; Lelj, F.; Olivella, S.; Sole, A.; Russo, N. J. Chem. Soc., Perkin Trans. 2 1986, 1517.
23. (c) Clark, T. J. Chem. Soc., Chem. Commun. 1986, 1774.
24. (d) Fueno, T.; Kamachi, M. Macromolecules 1988, 21, 908.
25. (e) Gonzales, C.; Sosa, C.; Schlegel, H. B. J. Phys. Chem. 1989, 93, 2435.
26. (f) Gonzales, C.; Sosa, C.; Schlegel, H. B. J. Phys. Chem. 1989, 93, 8388.
27. (g) Arnaud, R. New J. Chem. 1989, 13, 543.
28. (h) Zipse, H.; He, J.; Houk, K. N.; Giese, B. J. J. Am. Chem. Soc. 1991, 113, 4324.
29. (i) Arnaud, R.; Vidal, S. New J. Chem. 1992, 16, 471.
30. (j) Tozer, D. J.; Andrews, J. S.; Amos, R. D.; Handy, N. C. Chem. Phys. Lett. 1992, 199, 229.
31. (k) Schmidt, C.; Warken, M.; Handy, N. C. Chem. Phys. Lett. 1993, 211, 272.
32. (l) Wong, M. W.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1993, 115, 11050.
33. (m) Wong, M. W.; Pross, A.; Radom, L. Isr. J. Chem. 1993, 33, 415.
34. (n) Davis, T. P.; Rogers, S. C. Macromol. Theory Simul. 1994, 3, 905.
35. (o) Wong, M. W.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1994, 116, 6284.
36. (p) Wong, M. W.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1994, 116, 11938.
37. (q) Espinosa-Garcia, J.; Corchado, J. C.; Leroy, G. J. Phys. Chem. 1995, 99, 13926.
38. (r) Barone, V.; Orlandini, L. Chem. Phys. Lett. 1995, 246, 45.
39. See, for example: Wong, M. W.; Radom, L. J. Phys. Chem. 1995, 99, 8582.
40. For reviews, see, for example: (a) Pechukas, P. In Dynamics of Molecular Collisions, Part B; Miller, W. H., Ed.; Plenum Press: New York, 1976.
41. (b) Laidler, K. J.; King, M. C. J. Phys. Chem. 1983, 87, 2657.
42. (c) Truhlar, D. G.; Hase, W. L.; Hynes, J. T. J. Phys. Chem. 1983, 87, 2664.
43. (d) Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwell: Oxford, 1990.
44. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
45. Heuts, J. P. A.; Gilbert, R. G.; Radom, L. Macromolecules 1995, 28, 8771.
46. See, for example: Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules, Oxford University Press: New York, 1989.
47. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, K. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Repogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzales, C.; Matin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. GAUSSIAN 92, Revision D.3; Gaussian Inc.: Pittsburgh, PA, 1992.
48. (b) 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.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Repogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Revision B.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
49. (c) Stanton, J. F.; Gauss, J.; Watts, J. D.; Lauderdale, W. J.; Bartlett, R. J. ACES II, Version 0.2; Quantum Theory Project, Departments of Chemistry and Physics, University of Florida, Gainesville, 1992.
50. (d) Amos, R. D.; Alberts, I. L.; Andrews, J. S.; Colwell, S. M.; Handy, N. C; Jayatilaka, D.; Knowles, P. J.; Kohayashi, R.; Koga, N.; Laidig, K. E.; Maslen, P. E.; Murray, C. W.; Rice, J. E.; Sanz, J.; Simandiras, E. D.; Stone, A. J.; Su, M. D. CADPAC5, Department of Chemistry, University of Cambridge, Cambridge, England, 1992.
51. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
52. (a) Amos, R. D.; Andrews, J. S.; Handy, N. C.; Knowles, P. J. Chem. Phys. Lett. 1991, 185, 256.
53. (b) Knowles, P. J.; Andrews, J. S.; Amos, R. D.; Handy, N. C.; Pople, J. A. Chem. Phys. Lett. 1991, 186, 130.
54. (c) Lauderdale, W. J.; Stanton, J. F.; Gauss, J.; Watts, J. D.; Bartlett, R. J. Chem. Phys. Lett. 1991, 187, 21.
55. See, for example: (a) Knowles, P. J.; Somasundran, K.; Handy, N. C.; Hirao, K. Chem. Phys. Lett. 1985, 113, 8.
56. (b) Handy, N. C.; Knowles, P. J.; Somasundram, K. Theor. Chim. Acta 1985, 68, 87.
57. (c) Gill, P. M. W.; Radom, L. Chem. Phys. Lett. 1986, 132, 16.
58. (d) Nobes, R. H.; Pople, J. A.; Radom, L.; Handy, N. C.; Knowles, P. J. Chem. Phys. Lett. 1987, 138, 481.
59. (e) Lepetit, M. B.; Pélissier, M.; Malrieu, J. P. J. Chem. Phys. 1988, 89, 998.
60. (f) Gill, P. M. W.; Pople, J. A.; Radom, L.; Nobes, R. H. J. Chem. Phys. 1988, 89, 7307.
61. (g) Jensen, F. Chem. Phys. Lett. 1990, 169, 519.
62. (h) Nobes, R. H.; Moncrieff, D.; Wong, M. W.; Radom, L.; Gill, P. M. W.; Pople, J. A. Chem. Phys. Lett. 1991, 182, 216.
63. (a) Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530.
64. (b) Schlegel, H. B. J. Phys. Chem. 1988, 92, 3075.
65. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
66. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
67. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
68. (a) Nordholm, S.; Bacskay, G. B. Chem. Phys. Lett. 1976, 42, 253.
69. (b) Bacskay, G. B. Unpublished work.
70. Gilbert, R. G.; Jordan, M. J. T.; Smith, S. C.; Pitt, I. G.; Greenhill, P. G. UNIMOL Program suite, available from the authors: School of Chemistry, University of Sydney, NSW 2006 Australia, or by electronic transfer from gilbert@chem.usyd.edu.au.
71. McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1976.
72. (a) Pople, J. A.; Schlegel, H. B.; Krishnan, R.; DeFrees, D. J.; Binkley, J. S.; Frisch, M. J.; Whiteside, R. A.; Hout, R. F.; Hehre, W. J. Int. J. Quantum Chem. Symp. 1981, 15, 269.
73. Pople, J. A.; Scott, A. P.; Wong, M. W.; Radom, L. Isr. J. Chem. 1993, 33, 415.
74. (a) Scott, A. P.; Radom, L. J. Phys. Chem., submitted.
75. (b) The Standard scale factors for theoretical frequencies in ref 22 were evaluated using a least-squares procedure and are thus most appropriate for high frequencies. They are useful, for example, for evaluating zero-point vibrational energies. The most important frequencies for the evaluation of vibrational partition functions and related thermodynamic quantities (e.g., enthalpy and entropy), however, are the low frequencies. With this in mind, the vibrational data in ref 22 were reexamined (ref 23a) leading to (i) scale factors for low frequencies of 1.0075 (HF/3-21G), 0.9061 (HF/6-31G(d)), 1.0485 (MP2/6-31G(d)), 1.0620 (B-LYP/6-31G(d)), 1.0013 (B3-LYP/6-31G(d)), and 1.0147 (QCISD/6-31G(d)) and (ii) scale factors for zero-point vibrational energies of 0.9207 (HF/3-21G), 0.9135 (HF/6-31G(d)), 0.9670 (MP2/6-31G(d)), 1.0126 (B-LYP/6-31G(d)), 0.9806 (B3-LYP/6-31G(d)), and 0.9776 (QCISD/6-31G(d)). We adopt these values in the present work.
76. (a) Stanton, J. F. J. Chem. Phys. 1994, 101, 371.
77. (b) Chen, W.; Schlegel, H. B. J. Chem Phys. 1994, 101, 5957.
78. (a) Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
79. (b) Bauschlicher, C. W.; Partridge, H. J. Chem. Phys. 1995, 103, 1788.
80. (c) Mebel, A. M.; Morokuma, K.; Lin, M. C. J. Chem. Phys. 1995, 103, 7414.
81. (d) Rauhut, G.; Pulay, P. J. Chem. Phys. 1995, 103, 1788.
82. Wilson, E. B.; Decius, J. C.; Cross, P. C. Molecular Vibrations; McGraw-Hill: New York, 1955.
83. See, for example: (a) Pitzer, K. S.; Gwinn, D. W. J. Chem. Phys. 1942, 10, 428.
84. (b) Lewis, G. N.; Randall, M. Thermodynamics, 2nd ed. (revised by K. S. Pitzer and L. Brewer); McGraw-Hill: New York, 1961.
85. (c) Troe, J. J. Chem. Phys. 1977, 66, 4758.
86. (d) Truhlar, D. G. J. Comput. Chem. 1991, 12, 266.
87. For the ethyl radical, see: (a) Pacansky, J.; Gardini, G. P.; Bargon, J. J. Am. Chem. Soc. 1976, 98, 2665.
88. (b) Pacansky, J.; Dupuis, M. J. Chem. Phys. 1978, 65, 4276.
89. (c) Pacansky, J.; Dupuis, M. J. Am. Chem. Soc. 1982, 104, 415.
90. (d) Claxton, T. A.; Graham, A. M. J. Chem. Soc., Faraday Trans. 2 1987, 83, 2307.
91. (e) Chettur, G.; Snelson, A. J. Phys. Chem. 1987, 91, 3488.
92. (d) Pacansky, J.; Koch, W.; Miller, M. D. J. Am. Chem. Soc. 1991, 113, 317.
93. (f) Quelch, G. E.; Gallo, M. M.; Schaefer, H. F. J. Am. Chem. Soc. 1992, 114, 8239.
94. (g) Sears, T. J.; Johnson, P. M.; Jin, P.; Oatis, S. J. Chem. Phys. 1996, 104, 781.
95. For the propyl radical, see: (a) Pacansky, J.; Dupuis, M. J. Chem. Phys. 1979, 71, 2095.
96. (b) Claxton, T. A.; Graham. A. M. J. Chem. Soc., Faraday Trans. 2 1988, 84, 121.
97. (c) Bernardi, F.; Fossey, J. J. Mol. Struct. (THEOCHEM) 1988, 180, 79.
98. (d) Pacansky, J.; Waltman, R. J.; Barnes, L. A. J. Phys. Chem. 1993, 97, 10694.
99. Kerr, J. A.; Parsonage, M. J. Evaluated Kinetic Data on Gas Phase Reactions; Butterworths: London, 1972.
100. The frequency factor results given in this paper differ slightly from those given in ref 8, because the scale factors for the frequencies differ slightly from the values used previously. A sensitivity analysis of the scale factor dependence of the frequency factor has been included in ref 8.
101. Schweer, J. Ph.D. Thesis. Göttingen University, Germany, 1988.
102. Curtiss, L. A.; Redfern, P. C.; Smith, B. J.; Radom, L. J. Chem. Phys. 1996, 104, 5148.