Theoretical study on the factors controlling the accessibility of cationic metal centers in zirconocene polymerization catalysts

Macromolecules

Volumn 33, Issue 25, 2000, Pages 9205-9214

  Linnolahti, Mikko ^a   Pakkanen, Tapani A ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CATIONIC POLYMERIZATION; COMPOSITION EFFECTS; CONFORMATIONS; MOLECULAR STRUCTURE; POSITIVE IONS; REACTION KINETICS;

CATIONIC METAL CENTERS; ELECTRONIC EFFECTS; ZIRCONOCENE POLYMERIZATION CATALYSTS;

METALLORGANIC POLYMERS;

EID: 0034498485     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0009101     Document Type: Article

References (142)

1. For a general introduction to metallocenes, see for example: Long, N. J. Metallocenes; Blackwell Science Ltd.: 1998.
2. See for example: (a) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
3. (b) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
4. (c) Kaminsky, W. Macromol. Chem. Phys. 1996, 197, 3907.
5. (d) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 143.
6. (e) Olabisi, O.; Atiqullah, M.; Kaminsky, W. J. Macromol. Sci. - Rev. Macromol. Chem. Phys. 1997, C37, 519.
7. (f) Soga, K.; Shiono, T. Prog. Polym. Sci. 1997, 22, 1503.
8. (g) Janiak, C. In Metallocenes: Synthesis, reactivity, applications; Togni, A., Halterman, R. L., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
9. For studies related to ethylene polymerization by group IV metallocenes, see: (a) Jolly, C. A.; Marynick, D. S. J. Am. Chem. Soc. 1989, 111, 7968.
10. (b) Prosenc, M.-H.; Janiak, C.; Brintzinger, H.-H. Organometallics 1992, 11, 4036.
11. (c) Janiak, C. J. Organomet. Chem. 1993, 452, 63.
12. (d) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919.
13. (e) Meier, R. J.; van Doremaele, G. H. J.; Iarlori, S.; Buda, F. J. Am. Chem. Soc. 1994, 116, 7274.
14. (f) Fusco, R.; Longo, L. Macromol. Theory Simul. 1994, 3, 895.
15. (g) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 432.
16. (h) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252.
17. (i) Lohrenz, J. C. W.; Woo, T. K.; Ziegler, T. J. Am. Chem. Soc. 1995, 117, 12793.
18. (j) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91.
19. (k) Fusco, R.; Longo, L. Macromol. Symp. 1995, 89, 197.
20. (l) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746.
21. (m) Fan, L.; Harrison, D.; Woo, T. K.; Ziegler, T. Organometallics 1995, 14, 2018.
22. (n) Margl, P.; Lohrenz, J. C. W.; Ziegler, T.; Blöchl, P. E. J. Am. Chem. Soc. 1996, 118, 4434.
23. (o) Woo, T, K.; Margl, P. M.; Lohrenz, J. C. W.; Blöchl, P. E.; Ziegler, T. J. Am. Chem. Soc. 1996, 118, 13021.
24. (p) van Doremaele, G. H. J.; Meier, R. J.; Iarlori, S.; Buda, F. J. Mol. Struct.: Theochem. 1996, 363, 269.
25. (q) Støvneng, J. A.; Rytter, E. J. Organomet. Chem. 1996, 519, 277.
26. (r) Cavallo, L.; Guerra, G. Macromolecules 1996, 29, 2729.
27. (s) Iarlori, S.; Buda, F.; Meier, R.; van Doremaele, G. H. J. Mol. Phys. 1996, 87, 801.
28. (t) Cruz, V. L.; Muñoz-Escalona, A.; Martinez-Salazar, J. Polymer 1996, 37, 1663.
29. (u) Woo, T. K.; Margl, P. M.; Ziegler, T.; Blöchl, P. E. Organometallics 1997, 16, 3454.
30. (v) Margl, P. M.; Woo, T. K.; Ziegler, T. Organometallics 1998, 17, 4997.
31. (w) Petitjean, L.; Pattou, D.; Ruiz-López, M. F. J. Phys. Chem. B 1999, 103, 27.
32. For studies related to propylene polymerization by group IV metallocenes, see: (a) Venditto, V.; Guerra, G.; Corradini, P.; Fusco, R. Polymer 1990, 31, 530.
33. (b) Cavallo, L.; Guerra, G.; Vacatello, M.; Corradini, P. Macromolecules 1991, 24, 1784.
34. (c) Cavallo, L.; Corradini, P.; Guerra, G.; Vacatello, M. Polymer 1991, 32, 1329.
35. (d) Corradini, P.; Guerra, G. Prog. Polym. Sci. 1991, 16, 239.
36. (e) Castonguay, L. A.; Rappé, A. K. J. Am. Chem. Soc. 1992, 114, 5832.
37. (f) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
38. (g) Corradini, P.; Busico, V.; Cavallo, L.; Guerra, G.; Vacatello, M.; Venditto, V. J. Mol. Catal. 1992, 74, 433.
39. (h) Hart, J. R.; Rappé, A. K. J. Am. Chem. Soc. 1993, 115, 6159.
40. (i) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988.
41. (j) Yu, Z.; Chien, J. C. W. J. Polym. Sci., Part A, Polym. Chem. 1995, 33, 125.
42. (k) Yu, Z.; Chien, J. C. W. J. Polym. Sci., Part A, Polym. Chem. 1995, 33, 1085.
43. (l) Guerra, G.; Corradini, P.; Cavallo, L.; Vacatello, M. Macromol. Symp. 1995, 89, 307.
44. (m) Cavallo, L.; Guerra, G.; Corradini, P. Gazz. Chim. Ital. 1996, 126, 463.
45. (n) Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. Macromolecules 1996, 29, 4834.
46. (o) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1996, 15, 766.
47. (p) Cavallo, L.; Corradini, P.; Guerra, G.; Resconi, L. Organometallics 1996, 15, 2254.
48. (q) van der Leek, Y.; Angermund, K.; Reffke, M.; Kleinschmidt, R.; Goretzki, R.; Fink, G. Chem. - Eur. J. 1997, 3, 585.
49. (r) Guerra, G.; Longo, P.; Cavallo, L.; Corradini, P.; Resconi, L. J. Am. Chem. Soc. 1997, 119, 4394.
50. (s) Toto, M.; Cavallo, L.; Corradini, P.; Moscardi, G.; Resconi, L.; Guerra, G. Macromolecules 1998, 31, 3431.
51. (t) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Mol. Struct.: THEOCHEM 1999, 461-462, 121.
52. For polymerization studies on higher olefins, functional monomers or copolymerization by group IV metallocenes, see: (a) Guerra, G.; Cavallo, L.; Corradini, P.; Fusco, R. Macromolecules 1997, 30, 677.
53. (b) Peluso, A.; Improta, R.; Zambelli, A. Macromolecules 1997, 30, 2219.
54. (c) Cruz, V. L.; Muñoz-Escalona, A.; Martinez-Salazar, J. J. Polym. Sci., Part A, Polym. Chem. 1998, 36, 1157.
55. (d) Ahjopalo, L.; Löfgren, B.; Hakala, K.; Pietilä, L.-O. Eur. Polym. J. 1999, 35, 1519.
56. (e) Guerra, G.; Longo, P.; Corradini, P.; Cavallo, L. J. Am. Chem. Soc. 1999, 121, 8651.
57. (f) Sustmann, R.; Sicking, W.; Bandermann, F.; Ferenz, M. Macromolecules 1999, 32, 4204.
58. Very recently, a couple of studies on metallocene-cocatalyst interactions have been published: (a) Fusco, R.; Longo, L.; Masi, F.; Garbassi, F. Macromol. Rapid Commun. 1997, 18, 433.
59. (b) Fusco, R.; Longo, L.; Masi, F.; Garbassi, F. Macromolecules 1997, 30, 7673.
60. (c) Lanza, G.; Fragalà, I. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 8257.
61. (d) Fusco, R.; Longo, L.; Proto, A.; Masi, F.; Garbassi, F. Macromol. Rapid Commun. 1998, 19, 257.
62. (e)Yao, S.; Shoji, T.; Iwamoto, Y.; Kamei, E. Comput. Theor. Polym. Sci. 1999, 9, 41.
63. (f) Chan, M. S. W.; Vanka, K.; Pye, C. C.; Ziegler, T. Organometallics 1999, 18, 4624.
64. (g) Klesing, A.; Bettonville, S. Phys. Chem. Chem. Phys. 1999, 1, 2373.
65. For related studies on other transition metal complexes than group IV metallocenes, see for example: (a) Siegbahn, P. E. M.; Strömberg, S.; Zetterberg, K. Organometallics 1996, 15, 5542.
66. (b) Svensson, M.; Matsubara, T.; Morokuma, K. Organometallics 1996, 15, 5568.
67. (c) Musaev, D. G.; Froese, R. D. J.; Svensson, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 367.
68. (d) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 1094.
69. (e) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177.
70. (f) Froese, R. D. J.; Musaev, D. G.; Matsubara, T.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 7190.
71. (g) Woo, T. K.; Margl, P. M.; Blöchl, P. E.; Ziegler, T. J. Phys. Chem. B 1997, 101, 7877.
72. (h) Jensen, V. R.; Børve, K. J. Organometallics 1997, 16, 2514.
73. (i) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581.
74. (j) Bernandi, F.; Bottoni, A.; Rossi, I. J. Am. Chem. Soc. 1998, 120, 7770.
75. (k) Coussens, B. B.; Buda, F.; Oevering, H.; Meier, R. J. Organometallics 1998, 17, 795.
76. (l) Musaev, D. G.; Froese, R. D. J.; Morokuma, K. Organometallics 1998, 17, 1850.
77. (m) Deng, L.; Ziegler, T.; Woo, T. K.; Margl, P.; Fan, L. Organometallics 1998, 17, 3240.
78. (n) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1999, 121, 6479.
79. (o) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. Organometallics 1999, 18, 373.
80. (p) Michalak, A.; Ziegler, T. Organometallics 1999, 18, 3998.
81. (q) Koga, N. Theor. Chem. Acc. 1999, 102, 285.
82. (r) Musaev, D.; Morokuma, K. Top. Catal. 1999, 7, 107.
83. Publications covering two or more of the categories above: (a) Musaev, D. G.; Froese, R. D. J.; Morokuma, K. New J. Chem. 1997, 21, 1269.
84. (b) Margl, P.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1998, 120, 5517.
85. (c) Margl, P.; Deng, L.; Ziegler, T. Organometallics 1998, 17, 933.
86. (d) Margl, P.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1999, 121, 154.
87. (e) Margl, P.; Deng, L.; Ziegler, T. Top. Catal. 1999, 7, 187.
88. In addition, a variety of related studies not exactly matching the categories above have been published. See for example: (a) Fujimoto, H.; Yamasaki, T.; Mizutani, H.; Koga, N. J. Am. Chem. Soc. 1985, 107, 6157.
89. (b) Hansen, L. M.; Marynick, D. S. Organometallics 1989, 8, 2173.
90. (c) Hyla-Kryspin, I.; Gleiter, R.; Krüger, C.; Zwettler, R.; Erker, G. Organometallics 1990, 9, 517.
91. (d) Erker, G.; Zwettler, R.; Krüger, C.; Hyla-Kryspin, I.; Gleiter, R. Organometallics 1990, 9, 524.
92. (e) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359.
93. (f) Endo, J.; Koga, N.; Morokuma, K. Organometallics 1993, 12, 2777.
94. (g) Gleiter, R.; Hyla-Kryspin, I.; Niu, S.; Erker, G. Organometallics 1993, 12, 3828.
95. (h) Fan, L.; Harrison, D.; Deng, L.; Woo, T. K.; Swerhone, D.; Ziegler, T. Can. J. Chem. 1995, 73, 989.
96. (i) Bierwagen, E. P.; Bercaw, J. E.; Goddard, W. A., III. J. Am. Chem. Soc. 1994, 116, 1481.
97. (j) de Boer, H. J. R.; Royan, B. W. J. Mol. Catal. 1994, 90, 171.
98. (k) Axe, F. U.; Coffin, J. M. J. Phys. Chem. 1994, 98, 2567.
99. (l) Jensen, V. R.; Børve, K. J.; Ystenes, M. J. Am. Chem. Soc. 1995, 117, 4109.
100. (m) Hyla-Kryspin, I.; Niu, S.; Gleiter, R. Organometallics 1995, 14, 964.
101. (n) Jensen, V. R.; Børve, K. J.; Westberg, N.; Ystenes, M. Organometallics 1995, 14, 4349.
102. (o) Prosenc, M.-H.; Brintzinger, H.-H. Organometallics 1997, 16, 3889.
103. (p) Griffiths, E. A. H.; Gould, I. R.; Ramdas, S. Chem. Commun. 1998, 2177.
104. (q) Margl, P. M.; Woo, T. K.; Blöchl, P. E.; Ziegler, T. J. Am. Chem. Soc. 1998, 120, 2174.
105. (r) Cavallo, L.; Guerra, G.; Corradini, P. J. Am. Chem. Soc. 1998, 120, 2428.
106. (s) Jemmis, E. D.; Giju, K. T. J. Am. Chem. Soc. 1998, 120, 6952.
107. (t) Improta, R.; Garzillo, C.; Peluso, A. J. Mol. Struct.: THEOCHEM 1998, 426, 249.
108. (u) Bernardi, F.; Bottoni, A.; Miscione, G. P. Organometallics 1998, 17, 16.
109. (v) King, W. A.; Di Bella, S.; Gulino, A.; Lanza, G.; Fragala, I. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 355.
110. (w) Axe, F. U.; Andzelm, J. W. J. Am. Chem. Soc. 1999, 121, 5396.
111. (a) Gassman, P. G.; Callstrom, M. R. J. Am. Chem. Soc. 1987, 109, 7875.
112. (b) Sishta, C.; Hathorn, R. M.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 1112.
113. (c) Eisch, J. J.; Pombrick, S. I.; Zheng, G. X. Organometallics 1993, 12, 3856.
114. Siegbahn, P. E. M. Adv. Chem. Phys. 1996, 93, 333.
115. Pyykkö, P. Chem. Rev. 1988, 88, 563.
116. Linnolahti, M.; Hirva, P.; Pakkanen, T. A. J. Comput. Chem., in press.
117. (a) Linnolahti, M.; Pakkanen, T. A.; Leino, R.; Luttikhedde, H. J. G.; Wilén, E.-C.; Näsman, J. H. To be published.
118. 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-Lahman, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
119. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
120. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
121. See Appendix 1 in Supporting Information.
122. Huzinaga, S. Gaussian Basis Sets for Molecular Calculations; Elsevier: Amsterdam, 1984.
123. (a) Burger, P.; Hortmann, K.; Brintzinger, H.-H. Macromol. Chem. Macromol. Symp. 1993, 66, 127.
124. (b) Hortmann, K.; Brintzinger, H.-H. New J. Chem. 1992, 16, 51.
125. Janiak, C.; Lange, K. C. H.; Versteeg, U.; Lentz, D.; Budzelaar, P. H. M. Chem. Ber. 1996, 129, 1517.
126. Mäkelä, N. I.; Knuuttila, H. R.; Linnolahti, M.; Pakkanen, T. A. J. Chem. Soc., Dalton Trans., in press.
127. The search was done in October 1998.
128. See Appendix 2 in Supporting Information.
129. See for example: (a) Spaleck, W.; Kiiber, F.; Winter, A.; Rohrmann, J.; Bachamann, B.; Antberg, M.; Dolle, V.; Paulus, E. F. Organometallics 1994, 13, 954.
130. (b) Stehling, U.; Diebold, J.; Kirsten, R.; Röll, W.; Brintzinger, H. H.; Jüngling, S.; Mülhaupt, R.; Langhauser, F. Organometallics 1994, 13, 964.
131. (c) Schneider, N.; Huttenloch, M. E.; Stehling, U.; Kirsten, R.; Schaper, F.; Brintzinger, H. H. Organometallics 1997, 16, 3413.
132. (a) Piccolrovazzi, N.; Pino, P.; Consiglio, G.; Sirono, A.; Moret, M.; Organometallics 1990, 9, 3098.
133. (b) Lee, I.-M.; Gauthier, W. J.; Ball, J. M.; Iyengar, B.; Collins, S. Organometallics 1992, 11, 2115.
134. (a) Leino, R.; Luttikhedde, H.; Wilén, C.-E.; Sillanpää, R.; Näsman, J. H. Organometallics 1996, 15, 2450.
135. (b) Leino, R.; Luttikhedde, H. J. G.; Lehmus, P.; Wilén, C.-E.; Sjöholm, R.; Lehtonen, A.; Seppälä, J. V.; Näsman, J. H. Macromolecules 1997, 30, 3477.
136. (c) Luttikhedde, H. J. G.; Leino, R.; Lehtonen, A.; Näsman, J. H. J. Organomet. Chem. 1998, 555, 127.
137. (d) Leino, R.; Luttikhedde, H. J. G.; Lehmus, P.; Wilen, C. E.; Sjöholm, R.; Lehtonen, A.; Seppälä, J. V.; Näsman, J. H. J. Organomet. Chem. 1998, 559, 65.
138. (e) Leino, R.; Luttikhedde, H. J. G.; Lehtonen, A.; Ekholm, P.; Näsman, J. H. J. Organomet. Chem. 1998, 558, 181.
139. (f) Härkki, O.; Lehmus, P.; Leino, R.; Luttikhedde, H. J. G.; Näsman, J. H.; Seppälä, J. V. Macromol. Chem. Phys. 1999, 200, 1561.
140. (g) Lehmus, P.; Härkki, O.; Leino, R.; Luttikhedde, H. J. G.; Näsman, J. H.; Seppälä, J. V. Macromolecules 1999, 32, 3547.
141. (a) Barsties, E.; Schaible, S.; Prosenc, M. H.; Rief, U.; Röll, W.; Weyland, O.; Dorer, B.; Brintzinger, H. H. J. Organomet. Chem. 1996, 520, 63.
142. (b) Luttikhedde, H. J. G.; Leino, R. P.; Wilen, C.-E.; Näsman, J. H.; Ahlgren, M. J.; Pakkanen, T. A. Organometallics 1996, 15, 3092.