Role of MAO in chromium-catalyzed ethylene tri- and tetramerization: A DFT study

Organometallics

Volumn 26, Issue 4, 2007, Pages 1000-1013

  Van Rensburg, Werner Janse ^a   Van Den Berg, Jan Albert ^a   Steynberg, Petrus J ^a  

^a SASOL TECHNOLOGY PTY LTD   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CHROMIUM; COMPLEXATION; ETHYLENE; MOLECULAR STRUCTURE;

ION-PAIR COMPLEXES; METHYLALUMINOXANE (MAO); OLIGOMERIZATION; STERIC CONGESTION;

PARAFFINS;

EID: 33847324462     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060890c     Document Type: Article

References (117)

1. Chen, E.Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
2. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 4, 467.
3. (c) Angermund, K.; Fink, G.; Jensen, V. R., Kleinschmidt, R. Chem. Rev. 2000, 100, 1457.
4. (d) Coates, G. W. Chem. Rev. 2000, 100, 1223.
5. (a) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 4, 467.
6. (b) Angermund, K.; Fink, G.; Jensen, V. R., Kleinschmidt, R. Chem. Rev. 2000, 100, 1457.
7. (c) Coates, G. W. Chem. Rev. 2000, 100, 1223.
8. (a) Flory, P. J. J. Am. Chem. Soc. 1940, 62, 1561.
9. (b) Schulz, G. V. Z. Phys. Chem. B 1935, 30, 379.
10. (c) Schulz, G. V. Z. Phys. Chem. B 1939, 43, 25.
11. Cossee, P. J. J. Catal. 1964, 3, 80.
12. (b) Arlman, E. J.; Cossee, P. J. J. Catal. 1964, 3, 99.
13. For a comprehensive review on ethylene trimerization see: Dixon, J. T.; Green, M. J.; Hess, F. M.; Morgan, D. H. J. Organomet. Chem. 2004, 689, 3641.
14. Bollmann, A.; Blann, K.; Dixon, J. T.; Hess, F. M.; Killian, E.; Maumela, H.; McGuinness, D. S.; Morgan, D. H.; Neveling, A.; Otto, S.; Overett, M. J.; Slawin, A. M. Z.; Wasserscheid, P.; Kuhlmann, S. J. Am. Chem. Soc. 2004, 126, 14712.
15. Overett, M. J.; Blann, K.; Bollmann, A.; Dixon, J. T.; Hess, F. M.; Killian, E.; Maumela, H.; Morgan, D. H.; Neveling, A.; Otto, S. Chem. Commun. 2005, 622.
16. (a) Jolly, P. W. Acc. Chem. Res. 1996, 29, 544.
17. (b) Emrich, R.; Heinemann, O.; Jolly, P. W.; Kruger, C.; Verhovnik, G. P. J. Organometallics 1997, 16, 1511.
18. (a) Briggs, J. R. J. Chem. Soc., Chem. Commun. 1989, 674.
19. (b) Meijboom, N.; Schaveien, C.; Orpen, A. G. Organometallics 1990, 9, 774.
20. Agapie, T.; Schofer, S. J.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2004, 125, 1304. .
21. Overett, M. J.; Blann, K.; Bollmann, A.; Dixon, J. T.; Haasbroek, D.; Killian, E.; Maumela, H.; McGuinness, D. S.; Morgan, D. H. J. Am. Chem. Soc. 2005, 127, 10723.
22. Janse van Rensburg, W.; Grové, C.; Steynberg, J. P.; Stark, K. B.; Huyser, J. J.; Steynberg, P. J. Organometallics 2004, 23, 1207.
23. (a) Blok, A. N. J.; Budzelaar, P. H. M.; Gal, A. W. Organometallics 2003, 22, 2564.
24. (b) de Bruin, T. J. M.; Magna, L.; Raybaud, P.; Toulhoat, H. Organometallics 2003, 22, 3404.
25. (c) Tobisch, S.; Ziegler, T. Organometallics 2003, 22, 5392.
26. (d) Tobisch, S.; Ziegler, T. J. Am. Chem. Soc. 2004, 126, 9059.
27. (e) Tobisch, S.; Ziegler, T. Organometallics 2004, 23, 4077.
28. (f) Tobisch, S.; Ziegler, T. Organometallics 2005, 24, 256.
29. Yu, Z.-X.; Houk, K. N. Angew. Chem., Int. Ed. 2003, 42, 808.
30. Macchioni, A. Chem. Rev. 2005, 105, 2039.
31. Lanza, G.; Fragalà, I. L.; Marks, T. J. Organometallics 2002, 21, 5594.
32. (a) Vanka, K.; Chan, M. S. W.; Pye, C. C.; Ziegler, T. Organometallics 2000, 19, 1841.
33. (b) Chan, M. S. W.; Vanka, K.; Pye, C. C.; Ziegler, T. Organometallics 1999, 18, 4624.
34. (c) Wondimagegn, T.; Xu, Z.; Vanka, K.; Ziegler, T. Organometallics 2005, 24, 2076.
35. (d) Wondimagegn, T.; Vanka, K.; Xu, Z.; Ziegler, T. Organometallics 2004, 23, 2651.
36. (e) Vanka, K.; Xu, Z.; Ziegler, T. Organometallics 2004, 23, 2900.
37. (f) Vanka, K.; Ziegler, T. Organometallics 2001, 20, 905.
38. (g) Xu, Z.; Vanka, K.; Ziegler, T. Organometallics 2004, 23, 104.
39. (h) Chan, M. S.W.; Ziegler, T. Organometallics 2000, 19, 5182.
40. (i) Wondimagegn, T.; Xu, Z.; Vanka, K.; Ziegler, T. Organometallics 2004, 23, 3847.
41. (j) Vanka, K.; Xu, Z.; Ziegler, T. Organometallics 2005, 24, 419.
42. (k) Deck, P. A.; Beswick, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1772.
43. (l) Lanza, G.; Fragalà, I. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 8257.
44. (m) Lanza, G.; Fragalà, I. L.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 12764.
45. (n) Nifant'ev, I. E.; Ustynyuk, L. Y.; Laikov, D. N. Organometallics 2001, 20, 5375.
46. (o) Nifant'ev, I. E.; Ustynyuk, L. Y.; Besedin, D. V. Organometallics 2003, 22, 2619.
47. Xu, Z.; Vanka, K.; Firman, T.; Michalak, A.; Zurek, E.; Zhu, C.; Ziegler, T. Organometallics 2002, 21, 2444.
48. (a) Zurek, E.; Zieger, T. Faraday Disuss. 2003, 124, 93.
49. (b) Zurek, E.; Ziegler, T. Organometallics 2002, 21, 83.
50. (a) Belelli, P. G.; Branda, M. M.; Castellani, N. J. J. Mol. Struct. A: Chem. 2003, 192, 9.
51. (b) Belelli, P. G.; Damiani, D. E.; Castellani, N. J. J. Mol. Struct. A: Chem. 2004, 208, 147.
52. (c) Belelli, P. G.; Castellani, N. J. J. Mol. Struct. A: Chem. 2006, 253, 52.
53. (a) Eilertsen, J. L.; Støvneng, J. A.; Ystenes, M.; Rytter, E. Inorg. Chem. 2005, 44, 4843.
54. (b) Yang, S. H.; Huh, J.; Jo, W. H. Macromolecules 2005, 38, 1402.
55. (c) Fusco, R.; Longo, L.; Proto, A.; Masi, F.; Garbassi, F. Macromol. Rapid. Commun. 1998, 19, 257.
56. Fusco, R.; Longo, L.; Masi, F.; Garbassi, F. Macromolecules 1997, 30, 7673.
57. (a) Mason, M. R.; Smith, J. M.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1993, 115, 4971-4984.
58. (b) Harlan, C. J.; Mason, M. R.; Barron, A. R. Organometallics 1994, 13, 2957-2969.
59. Babushkin, D. E.; Semikolenova, N. V.; Panchenko, V. N.; Sobolev, A. P., Zakharov, V. A.; Talsi, E. P. Macromol. Chem. Phys. 1997, 198, 3845-3854.
60. Zurek, E.; Ziegler, T. Inorg. Chem. 2001, 40, 3279.
61. (a) Zurek, E.; Ziegler, T. Prog. Polym. Sci. 2004, 29, 107.
62. (b) Zurek, E.; Woo, T. K.; Firman, T. K.; Ziegler, T. Inorg. Chem. 2001, 40, 361.
63. Zakharov, I. I.; Zakharov, V. A. Macromol. Theory Simul. 2001, 10, 108.
64. (a) Zakharov, I. I.; Zakharov, V. A.; Potapov, A. G.; Zhidomirov, G. M. Macromol. Theory Simul. 1999, 8, 272.
65. (b) Panchenko, V. N.; Zakharov, V. A.; Danilova, I. G.; Paukshtis, E. A.; Zakharov, I. I.; Goncharov, V. G.; Suknev, A. P. J. Mol. Catal. A 2001, 174, 107.
66. Ystenes, M.; Eilertsen, J. L.; Liu, J.; Ott, M.; Rytter, E.; Støvneng, J. A. J. Polym. Sci., Part A: Polym. Chem. 2000, 123, 3106.
67. Rytter, E.; Støvneng, J. A.; Eilertsen, J. A.; Ystenes, M. Organometallics 2001, 20, 4466.
68. Sinn, H. Macromol. Symp. 1995, 97, 27-52.
69. Watanabi, M.; McMahon, N.; Harlan, C. J.; Barron, A. R. Organometallics 2001, 20, 460-467.
70. Resconi, L.; Bossi, S.; Abis, L. Macromolecules 1990, 23, 4489.
71. (a) Pasynkiewics, S. Polyhedron 1990, 9, 429.
72. (b) Gianetti, E.; Nicoletti, G.; Mazzochi, R. J. Polym. Sci., Polym. Chem. Ed. 1985, 23, 2117.
73. Imhoff, D. W.; Simeral, L. S.; Sangokoya, S. A.; Peel, J. H. Organometallics 1998, 17, 1941-1945.
74. Sugano, T.; Matsubara, K.; Fujita, T.; Takahashi, T. J. Mol. Catal. 1993, 82, 93.
75. Siedle, A. R.; Lamanna, W. M.; Newmark, R. A.; Stevens, J.; Richardson, D. E.; Ryan, M. Macromol. Symp. 1993, 66, 215.
76. Siedle, A. R.; Newmark, R. A.; Lamanna, W. M.; Schroepfer, J. N.; Polyhedron 1990, 9, 301.
77. (a) Delley, B. J. Chem. Phys. 1992, 92, 508.
78. (b) Delley, B. J. Phys. Chem. 1996, 100, 6107.
79. (c) Delley, B. J. Chem. Phys. 2000, 113, 7756.
80. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
81. Hammer, B.; Hansen, L. B.; Nørskov, J. K. Phys. Rev. B 1999, 59, 7413.
82. Delley, B In Modern Density Functional Theory: A Tool for Chemistry; Seminario, J. M., Politzer, P., Eds.; Theoretical and Computational Chemistry, Vol. 2; Elsevier: Amsterdam, The Netherlands, 1995.
83. Andzelm, J.; King-Smith, R. D.; Fitzgerald, G. Chem. Phys. Lett. 2001, 335, 321.
84. (a) Hirshfeld, F. L. Theor. Chim. Acta B 1977, 44, 129.
85. (b) Wiberg, K. B.; Rablen, P. R. J. Comput. Chem. 1993, 1412, 1504.
86. (a) Cohen, R.; Weitz, E.; Martin, J. M. L.; Ratner, M. A. Organometallics 2004, 23, 2315.
87. (b) Collagne. E.; Duret, D.; Poli, R. Dalton Trans. 1999, 875.
88. (c) Cacelli, I.; Keogh, D. W.; Poli, R.; Rizzo, A. New J. Chem. 1997, 21, 133.
89. (d) Hess, J. S.; Leelasubcharoen, S.; Rheingold, A. L.; Doren, D. J.; Theopold, K. H. J. Am. Chem. Soc. 2002, 124, 2454.
90. (e) Hoganson, C. W.; Doren, D. J.; Theopold, K. H. Macromolecules 2004, 37, 566.
91. (a) Carney, M. J.; Robertson. N. J.; Halfen, J. A.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2004, 23, 6184-6190.
92. (b) Ganesan, M.; Gabbaï, F. P. Organometallics 2004, 23, 4608-4613.
93. (c) Agapie, T.; Day, M. W.; Henling, L. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2006, 25, 2733.
94. (d) Schofer, S. J.; Day, M. W.; Henling, L. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2006, 25, 2743.
95. Smith, M. B. J. Organomet. Chem. 1972, 46, 31.
96. Tosell, J. A. Oragnometallics 2002, 21, 4523-4527.
97. Kaminsky, W.; Steiger, R. Polyhedron 1988, 7, 2375.
98. Cam, D.; Giannini, U. Makromol. Chem. 1992, 193, 1049.
99. (a) Gassman, P. G.; Callstrom, M. R. J. Am. Chem. Soc. 1987, 109, 7875.
100. (b) Sishta, C.; Hathorn, R. M.; Marks, T. J. J. Am. Chem. Soc. 1992, 774, 1112.
101. (c) Siedle, A. R.; Lamanna, W. M.; Newmark, R. A.; Schroepfer, J. N. J. Mol. Catal. 1998, 128, 257.
102. (d) Tritto, I.; Li, S. X.; Sacchi, M. C.; Locatelli, P.; Zannoni, G. Macromolecules 1995, 28, 5358.
103. (e) Tritto, I.; Li, S. X.; Sacchi, M. C.; Zannoni, G. Macromolecules 1993, 26, 7111.
104. (f) Kaminsky, W. Makromol. Chem. Phys. 1996, 197, 3907.
105. (g) Kaminsky, W.; Strubel, C. J. Mol. Catal. 1998, 128, 191.
106. (h) Bryliakov, K. P.; Babushkin, D. E.; Talsi, E. P.; Voskoboynikov, A. Z.; Gritzo, H.; Schröder, L.; Damrau, H.-R. H.; Wieser, U.; Schaper, F.; Brintzinger, H. H. Organometallics 2005, 24, 894.
107. (i) Castro, P. M.; Lahtinen, P.; Axenov, K.; Viidanoja, J.; Kotiaho, T.; Leskelä, M.; Repo, T. Organometallics 2005, 24, 3664.
108. See Supporting Information for an analysis and validation of DFT-calculated spin state splittings for chromium complexes.
109. Harvey, J. N. Struct. Bonding 2004, 112, 151-184.
110. Rappé, A. K.; Skiff, W. M.; Casewit, C. J. Chem. Rev. 2000, 100, 1435.
111. Blann, K.; Bollmann, A.; Dixon, J. T.; Hess, F. M.; Killian, E.; Maumela, H.; Morgan, D. H.; Neveling, A.; Otto, S.; Overett, M. Chem. Commun. 2005, 620.
112. 9-TMA-sh, also resulted in no spontaneous dissociated ion-pair formation, in both the absence and presence of coordinated ethylene. Full details of these results are presented in the Supporting Information.
113. 16
114. Berthomieu, D.; Bscquet, Y.; Pedocchi, L.; Goursot, A. J. Phys. Chem. A 1998, 102, 7821.
115. Almenningen, A.; Halvorsen, S.; Haland, A. Acta Chem. Scand. 1971, 25, 1937.
116. Huffmann, J. C.; Streib, W. E. J. Chem. Soc. D 1971, 911.
117. McGrady, G. S.; Turner, J. F. C.; Ibberson, R. M.; Prager, M. Organometallics 2000, 19, 4398.