Copolymerization of ethylene with polar monomers by anionic substitution. Theoretical study based on acrylonitrile and the brookhart diimine catalyst

Organometallics

Volumn 24, Issue 9, 2005, Pages 2147-2156

  Szabo, Miklos J ^a   Galea, Natasha M ^a   Michalak, Artur ^b   Yang, Sheng Yong ^a   Groux, Laurent F ^a   Piers, Warren E ^a   Ziegler, Tom ^a  

^a UNIVERSITY OF CALGARY   (Canada)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; ETHYLENE; MONOMERS; RATE CONSTANTS; SUBSTITUTION REACTIONS;

ACRYLONITRILE; ANIONIC SUBSTITUTION; BROOKHART DIIMINE CATALYSTS; POLAR MONOMERS;

COPOLYMERIZATION;

EID: 18444372033     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049018z     Document Type: Article

References (69)

1. (a) Boffa, L. S.; Novak, B. M. Chem. Rev. 2000, 100, 1479.
2. (b) Gibson, V. C.; Spitzmeseer, S. K. Chem. Rev. 2003, 103, 283.
3. (a) Mecking, S. Coord. Chem. Rev. 2002, 203, 325.
4. (b) Zuideveld, M. A.; Wehnnann, P.; Röhr, C.; Mecking, S. Angew, Chem., Int. Ed. 2004, 43, 869.
5. Hagman, J. F.; Crary, J. W. Encyclopedia of Polymer Science and Engineering; Mark, H. F., Bikales, N. W., Overberger, C. G., Menges, G., Kroschwitz, J. I., Eds.; Wiley: New York, 1985; Vol. 1, p 325.
6. Stockland, R. A., Jr.; Foley, S. R.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 796.
7. (a) Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169.
8. (b) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1985, 117, 6414.
9. (c) Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 11664.
10. (d) Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888.
11. (e) Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 267. For other late-transition-metal ethylene polymerization catalysts, see the following reviews:
12. (f) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew, Chem., Int. Ed. 1999, 38, 428.
13. (g) Britovsek, G. J. P.; Gibson, V. C.; Hoarau, O. D.; Spitzmesser, S. K.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2003, 42, 3454.
14. (h) Foley, S. R.; Stockland, R. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350.
15. Helldörfer, M.; Backhaus, J.; Milius, W.; Alt, H. G. J. Mol. Catal. A 2003, 193, 59.
16. (a) Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedricj, S. K.; Grubbs, R. H.; Bansleben, D. A. Science 2000, 287, 460.
17. (b) Wang, C.; Friedrich, S.; Younkin, T. R.; Li, R. T.; Grubbs, R. H.; Bansleben, D. A.; Day, M. W. Organometallics 1998, 17, 3149.
18. (a) Keim, W.; Kowalt, F. H.; Goddard, R.; Krüger, C. Angew, Chem., Int. Ed. 1978, 17, 466.
19. (b) Drent, E.; Van Dijk, R.; Van Ginkel, R.; Van Oort, Z. B.; Pugh, R. I. Chem. Commun. 2002, 744.
20. (c) Drent, E.; Van Dijk, R.; Van Ginkel, R.; Van Oort, Z. B.; Pugh, R. I. Chem. Commun. 2002, 964.
21. (a) Komon, Z. J. A.: Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 1830.
22. (b) Komon, Z. J. A.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 12379.
23. (c) Lee, B. Y.; Bu, X.; Bazan, G. C. Organometallics 2001, 20, 5425.
24. (d) Kim, Y. H.; Kim, T. H.; Lee, B. Y.; Woodmansee, D.; Bu, X.; Bazan, G. C. Organometallics 2002, 21, 3082.
25. (e) Komon, Z. J. A.; Diamond, G. M.; Leclerc, M. K.; Murphy, V.; Okazaki, M.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 15280.
26. (f) Shim, C. B.; Kim, Y. H.; Lee, B. Y.; Dong, Y.; Yun, H. Organometallics 2003, 22, 4272.
27. (a) Thomas, J. C.; Peters, J. C. Inorg. Chem. 2003, 42, 5055.
28. (b) Lu, C. C.; Peters, J. C. J. Am. Chem. Soc. 2002, 124(19), 5272.
29. Philipp, D. M.; Muller, R. P.; Goddard, W. A. III; Storer, J.; McAdon, M.; Mullins, M. J. Am. Chem. Soc. 2002, 124, 10198.
30. von Schenck, H.; Stromberg, S.; Zetterberg, K.; Ludwig, M.; Akermark, B.; Svensson, M. Organometallics 2001, 20, 2813.
31. (a) Deubel, D. V.; Ziegler, T. Organometallics 2002, 21, 1603.
32. (b) Deubel, D. V.; Ziegler, T. Organometallics 2002, 21, 4432.
33. (c) Michalak, A.; Ziegler, T. Organometallics 2001, 20, 1521.
34. (d) Michalak, A.; Ziegler, T. J. Am. Chem. Soc. 2001, 123, 12266.
35. (e) Michalak, A.; Ziegler, T. Organometallics 1999, 18, 3998.
36. (f) Michalak, A.; Ziegler, T. Organometallics 2000, 19, 1850.
37. (g) Michalak, A.; Ziegler, T. Organometallics 2003, 22, 2660.
38. (h) Szabo, M. J.; Jordan, R. F.; Michalak, A.; Piers, W. E.; Weiss, T.; Yang, S.-Y.; Ziegler, T. Organometallics 2004, 23, 5565.
39. Szabo, M. J.; Galea, N. M.; Mickalak, A.; Yang, S.-Y.; Groux, L. F.; Piers, W. E.; Ziegler, T. Manuscript in preparation.
40. Groux, L. F.; Weiss, T.; Reddy, D. N.; Chase, P. A.; Piers, W. A.; Ziegler. T.; Parvez, M.: Benet-Buchholz, J. J. Am. Chem. Soc. 2005, 127, 1854.
41. Becke, A. Phys. Rev. A 1988, 38, 3098.
42. Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
43. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
44. Baerends, E. J. Ph.D. Thesis, Free University, Amsterdam, The Netherlands, 1973.
45. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
46. Ravenek, W. In Algorithms and Applications on Vector and Parallel Computers; te Riele, H. J. J., Dekker: T. J., van de Horst, H. A., Eds.; Elsevier: Amsterdam, The Netherlands, 1987.
47. Boerrigter, P. M.; te Velde, G.; Baerends, E. J. Int. J. Quantum Chem. 1988, 33, 87.
48. te Velde, G.; Baerends, E. J. J. Comput. Chem. 1992, 99, 84.
49. Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322.
50. Snijders, J. G.; Baerends, E. J.; Vernoijs, P. At. Nucl. Data Tables 1982, 26, 483.
51. Vernoijs, P.; Snijders, J. G.; Baerends, E. J. Slater Type Basis Functions for the Whole Periodic System; Internal report (in Dutch); Department of Theoretical Chemistry, Free University, Amsterdam, The Netherlands, 1981.
52. Krijn, J.; Baerends, E. J. Fit Functions in the HFS Method; Internal Report (in Dutch); Department of Theoretical Chemistry, Free University, Amsterdam, The Netherlands, 1984.
53. Ziegler, T.; Tschinke, V.; Baerends, E. J.; Snijders, J. G.; Ravenek, W. J. Phys. Chem. 1989, 93, 3050.
54. Snijders, J. G.; Baerends, E. J. Mol. Phys. 1978, 36, 1789.
55. Snijders, J. G.; Baerends, E. J.; Ros, P. Mol. Phys. 1979, 38, 1909.
56. Woo, T. K.; Cavallo, L.; Ziegler, T. Theor. Chem. Acc. 1998, 100, 307.
57. Clark, M.; Cramer, R. D., III; van Opdenbosch, N. J. Comput. Chem. 1989, 10, 982.
58. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
59. Woo, T. K.; Zegler, T. J. Organomet. Chem. 1999, 591, 204.
60. Peuckert, M.; Keim, W. Organometallics 1983, 2, 594.
61. Woo, T. K.; Blöchl, P. E.; Ziegler, T. J. Phys. Chem. A 2000, 104, 121.
62. Waters, J. A.; Mortimer, G. A.; Clements, H. E. J. Chem. Eng. Data 1970, 15, 174.
63. Deng, L.; Ziegler, T.; Woo, T. K.; Margl, P.; Fan, L. Organometallics 1998, 17, 3240.
64. Michalak, A.; DeKock, R. L.; Ziegler., T. Manuscript in preparation. The bond order method employed in this work is a modification of that published by Nalewajski and co-workers:
65. (a) Nalewajski, R. F.; Mrozek, J. Int. J. Quantum Chem. 1994, 51, 187.
66. (b) Nalewajski, R. F.; Mrozek, J.; Michalak, A. Int. J. Quantum Chem. 1997, 61, 589.
67. (c) Nalewajski, R. F.; Mrozek, J.; Mazur, G. Can. J. Chem. 1996, 74, 1121.
68. (d) Nalewajski, R. F.; Mrozek, J.; Michalak, A. Polish J. Chem. 1998, 72, 1779.
69. (e) Michalak, A.; Ziegler, T. Organometallics 2003, 22, 2069.