Theoretical study on Bis(imino)pyridyl-Fe(II) olefin poly- and oligomerization catalysts. Dominance of different spin states in propagation and β-hydride transfer pathways

Organometallics

Volumn 20, Issue 10, 2001, Pages 2007-2026

  Khoroshun, Dmitry V ^a   Musaev, Djamaladdin G ^a   Vreven, Thom ^a   Morokuma, Keiji ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BISIMINOPYRIDYL IRON OLEFIN; HYDRIDE TRANSFER; INTEGRATED MOLECULAR ORBITALS; MOLECULAR MECHANICS; OLIGOMERIZATION; SPIN STATES;

CATALYSTS; ELECTRON ENERGY LEVELS; ENTROPY; GROUND STATE; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; MOLECULAR ORIENTATION; NUMERICAL ANALYSIS; OLEFINS; OLIGOMERS; POLYMERIZATION; PROBABILITY DENSITY FUNCTION;

ORGANOMETALLICS;

EID: 0035858956     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010126k     Document Type: Article

References (114)

1. (a) Freemantle, M. New catalysts to polymerize olefins. Chem. Eng. News 1998, Apr 13, 11-12.
2. (b) Britovsek, G. J. P.; Gibson, V. G.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P., Williams, D. J. Chem. Commun. 1998, 1998, 849.
3. (c) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
4. (d) Small, B. L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 7143.
5. (e) Britovsek, G. J. P.; Bruce, M.; Gibson, V. G.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Stroemberg, S.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 8728.
6. (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. S. J. Am. Chem. Soc. 1995, 117, 6414.
7. (b) Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M. S. J. Am. Chem. Soc. 1996, 118, 11664.
8. (a) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177.
9. (b) Froese, R. D. J.; Musaev, D. G.; Morokuma, K.; J. Am. Chem. Soc. 1998, 120, 1581.
10. (c) Musaev, D. G.; Froese, R. D. J.; Morokuma, K. Organometallics 1998, 17, 1850.
11. Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1996, 15, 766.
12. Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107.
13. (a) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1999, 121, 6479.
14. (b) Griffiths, E. A. H.; Britovsek, G. J. P.; Gibson, V. C.; Gould, I. R. Chem. Commun. 1999, 1999, 1333.
15. (a) Nartin, L. M.; Hagen, K. S.; Hauser, A.; Martin, R. L.; Sargeson, A. M. J. Chem. Soc., Chem. Commun. 1988, 1988, 1313.
16. (b) Diebold, A.; Hagen, K. S. Inorg. Chem. 1998, 37, 215.
17. (c) Guetlich, P. Coord. Chem. Rev. 1990, 97, 1.
18. (d) Guetlich, P.; Jung, J. J. Mol. Struct. 1995, 347, 21.
19. (e) Hauser, A.; Jeftic, J.; Romstedt, H.; Hinek, R.; Spiering, H. Coord. Chem. Rev. 1999, 190-192, 471.
20. (a) Hawkins, T. W.; Hall, M. B. Inorg. Chem. 1980, 19, 1735.
21. (b) Kashiwagi, H.; Obara, S. Int. J. Quantum Chem. 1981, 20, 843.
22. (c) Obara, S.; Kashiwagi, H. J. Chem. Phys. 1982, 77, 3155.
23. (d) Rohmer, M.-M.; Dedeiu, A.; Veillard, A. Chem. Phys. 1983, 77, 449.
24. (e) Sontum, S. F.; Case, D. A.; Karplus, M. J. Chem. Phys. 1983, 79, 2881.
25. (f) Strich, A.; Veillard, A. Nouv. J. Chem. 1983, 7, 347.
26. (g) Newton, J. E.; Hall, M. B. Inorg. Chem. 1984, 23, 4627.
27. (h) Rohmer, M.-M.; Strich, A.; Veillard, A. Theor. Chim. Acta 1984, 65, 219.
28. (i) Rawling, D. C.; Gouterman, M.; Davidson, E. R.; Feller, D. Int. J. Quantum Chem. 1985, 28, 773.
29. (j) Rawling, D. C.; Gouterman, M.; Davidson, E. R.; Feller, D. Int. J. Quantum Chem. 1985, 28, 797.
30. (k) Rohmer, M.-M. Chem. Phys. Lett. 1985, 116, 44.
31. (l) Saito M.; Kashiwagi, H. J. Chem. Phys. 1985, 82, 848.
32. (m) Sontum, S. F.; Case, D. A. J. Am. Chem. Soc. 1985, 107, 4013.
33. (n) Edwards, W. D.; Weiner, B.; Zerner, M. C. J. Am. Chem. Soc. 1986, 108, 2196.
34. (o) Saito, M.; Kashiwagi, H. Int. J. Quantum Chem. Quantum Chem. Symp. 1987, 21, 661.
35. (p) Rohmer, M.-M. Inorg. Chem. 1989, 28, 4574.
36. (q) Delley, B. In Density Functional Methods in Chemistry; Labanowski, J. K., Andzelm, J. W., Eds.; Springer-Verlag: New York, 1991; Chapter 7.
37. (r) Delley, B. Physica B 1991, 172, 185.
38. (s) Sahoo, N.; Ramani Lata, K.; Das, T. P. Theor. Chim. Acta 1992, 82, 285.
39. (t) Matsuzawa, N.; Ata, M.; Dixon, D. A. J. Phys. Chem. 1995, 99, 7698.
40. (u) Belazoni, P.; N., Re.; Rosi, M.; Sgamellotli, A.; Baerends, E. J.; Floriani, C. Inorg. Chem. 1996, 35, 7776.
41. (v) Zwaans, R.; van Lenthe, J. H.; den Boer, D. H. W. J. Mol. Struct.: THEOCHEM 1996, 367, 15.
42. (w) Lehnert, N.; Wiesler, B. E.; Tuczek, F.; Hennige, A.; Sellmann, D. J. Am. Chem. Soc. 1997, 119, 8869.
43. (x) Rovira, C.; Kunc, K.; Hutter, J.; Ballone, P.; Parrinello, M. J. Phys. Chem. A 1997, 101, 8914.
44. (y) Choe, Y.-K.; Hashimoto, T.; Nakano, H.; Hirao, K. Chem. Phys. Lett. 1998, 295, 380.
45. (z) Kozlowski, P. M.; Spiro, T. G.; Bérces, A.; Zgierski, M. Z. J. Chem. Phys. B 1998, 102, 2603.
46. (aa) Choe, Y.-K.; Nakajima, T.; Hirao, K. J. Chem. Phys. 1999, 111, 3837.
47. (bb) Vogel, K. M.; Kozlowski, P. M.; Zgierski, M. Z.; Spiro, T. G. J. Am. Chem. Soc. 1999, 121, 9915.
48. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
49. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
50. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.;Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT; Gaussian Inc, Pittsburgh, PA, 1993.
51. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
52. J. S. Binkley, J. A. Pople, W. J. Hehre, J. Am. Chem. Soc. 1980, 102, 939.
53. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1977; Vol. 3, pp 1-27.
54. Hay. P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
55. (a) Delley, B.; Wrinn, M.; Lüthi, H. P. J. Chem. Phys. 1994, 100, 5785.
56. (b) Russo, T. V.; Martin, R. L.; Hay, P. J. J. Chem. Phys. 1994, 101, 7729.
57. (c) Eriksson, L. A.; Petersson, L. G. M.; Siegbahn, P. E. M.; Wahlgren, U. J. Chem. Phys. 1995, 102, 872.
58. (d) Holthausen, M. C.; Heinemann, C.; Cornehl, H. H.; Koch, W.; Schwarz, H. J. Chem. Phys. 1995, 102, 4931.
59. (e) Holthausen, M. C.; Mohr, M.; Koch, W. Chem. Phys. Lett. 1995, 240, 245.
60. (f) Ricca, A.; Bauschlicher, C. W., Jr. Theor. Chim. Acta 1995, 92, 123.
61. (g) Salahub, D. R.; Chrétien, S.; Milet, A.; Proynov, E. I. Performance of Density Functionals for Transition States. In Transition State Modeling for Catalysis; Truhlar, D. G., Morokuma, K., Eds.; ACS Symposium Series 721; American Chemical Society: Washington, DC, 1999; pp 20-32.
62. Davidson, E. R. Chem. Rev. 2000, 100, 351, and reviews in the same issue.
63. (a) Maseras, F.; Morokuma, K. J. Comput. Chem. 1995, 16, 1170.
64. (b) Matsubara, T.; Maseras, F.; Koga, N.; Morokuma, K. J. Phys. Chem. 1996, 100, 2573.
65. (c) Matsubara, T.; Sieber, S.; Morokuma, K. Int. J. Quantum Chem. 1996, 60, 1101.
66. Pettersson, I.; Liljefors, T. Molecular Mechanics Calculated Conformational Energies of Organic Molecules: A Comparison of Force Fields. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH; New York, 1996; Vol. 9, pp 167-189.
67. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A, III; Skiff, W. M.; J. Am. Chem. Soc. 1992, 114, 10024.
68. (a) Barea, G.; Maseras, F.; Jean, Y.; Lledos, A. Inorg. Chem. 1996, 35, 6401.
69. (b) Froese, R. D. J.; Morokuma, K. Chem. Phys. Lett. 1996, 263, 393.
70. (c) Svensson, M.; Humbel, S.; Froese, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1996, 100, 19357.
71. (d) Ujaque, G.; Maseras, F.; Lledos, A. Theor. Chim. Acta 1996, 94, 67.
72. (e) Ujaque, G.; Maseras, F.; Eisenstein, O. Theor. Chem. Acc. 1997, 96, 146.
73. (f) Ujaque, G.; Maseras, F.; Lledos, A. J. Org. Chem. 1997, 62, 7892.
74. (g) Wakatsuki, Y.; Koga, N.; Werner, H.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 360.
75. (h) Barea, G.; Lledos, A.; Maseras, F.; Jean, Y. Inorg. Chem. 1998, 37, 3321.
76. (i) Jaffart, J.; Mathieu, R.; Etienne, M.; McGrady, J. E.; Eisenstein, O.; Maseras, F. Chem. Commun. 1998, 18, 2011.
77. (j) Maseras, F. New J. Chem 1998, 22, 327.
78. (k) Maseras, F.; Eisenstein, O. New J. Chem 1998, 22, 5.
79. (l) Ulajaque, G.; Cooper, A. C.; Maseras, F.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1998, 120, 361.
80. (m) Ujaque, G.; Maseras, F.; Eisenstein, O.; Liable-Sands, L.; Rheingold, A. L.; Yao, W.; Crabtree, R. H. New J. Chem 1998, 22, 1493.
81. (n) Woo, T. K.; Cavallo, L.; Ziegler, T. Theor. Chem. Acc. 1998, 100, 307.
82. (o) Aiga, F.; Tada, T. Int. J. Quantum Chem. 1999, 71, 403.
83. (p) Cooper, A. C.; Clot, E.; Huffman, J. C.; Streib, W. E.; Maseras, F.; Eisenstein O.; Caulton, K. G. J. Am. Chem. Soc. 1999, 121, 97.
84. (q) Dapprich, S.; Komaromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. J. Mol. Struct.: THEOCHEM 1999, 461-462, 1.
85. (r) Khoroshun, D. V.; Musaev, D. G.; Morokuma, K. Organometallics 1999, 18, 5653.
86. (s) Margl, P.; Deng, L.; Ziegler, T. Organometallics 1999, 18, 5701.
87. (t) Maseras, F. Top. Organomet. Chem. 1999, 4, 165.
88. (u) Shoemaker, J. R.; Burggraf, L. W.; Gordon, M. S. J. Phys. Chem. A 1999, 103, 3245.
89. (v) Ujaque, G.; Maseras, F.; Lledos, A. J. Am. Chem. Soc. 1999, 121, 1317.
90. (w) Woo, T. K.; Margl, P. M.; Deng, L.; Cavallo, L.; Ziegler, T. Catal. Today 1999, 50, 479.
91. (x) Woo, T. K.; Ziegler, T. J. Organomet. Chem. 1999, 591, 204.
92. (y) Woo, T. K.; Bloechl, P. E.; Ziegler, T. J. Phys. Chem. A 2000, 104, 121.
93. Dolg, M.; Wedig, U.; Soll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866.
94. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
95. 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.; 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.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision A.1; Gaussian Inc.: Pittsburgh, PA, 1995.
96. (a) MM3(92), Quantum Chemistry Program Exchange; Indiana University, 1992.
97. (b) Aped, A.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1.
98. 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.; Baboul, A. G.; 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
99. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14, 123.
100. (a) Cossee, P. J. Catal. 1964, 3, 80.
101. (b) Arlman, E. J. J. Catal. 1964, 3, 89.
102. Koga, N.; Morokuma, K. Chem. Rev. 1991, 91, 823.
103. Seeman, J. I. Chem. Rev. 1983, 83, 83.
104. π.
105. 11 subsystem is treated with the D95V basis set in both BSI and BSII. To assess the difference in geometrical parameters introduced by the variation in the basis set, we reoptimized all nine LSB species m-I at the B3LYP/BSII level and performed B3LYP/BSIII single-point calculations. Supporting Information Table S9 gives the absolute energies at the two levels, B3LYP/BSIII//B3LYP/BSI and B3LYP/BSIII//B3LYP/ BSI, as well as the value of difference between the two. The range of the difference is -2 to +2 kcal/mol.
106. Describing the quintet species as distorted from octahedral (square pyramid) geometry, we avoid complications of switching to trigonal bipyramid point of view at the ligand arrangement, keeping the effect of the bulky ligands (hindrance of the axial positions of the octahedral configuration) clearer.
107. (a) Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, FRG, 2000; pp 251-259.
108. (b) Holthausen, M. C.; Fiedler, A.; Schwarz, H.; Koch, W. J. Phys. Chem. 1996, 100, 6236.
109. (c) Holthausen, M. C.; Koch, W. J. Am. Chem. Soc. 1996, 118, 9932.
110. (a) Wang, W.; Weitz, E. J. Phys. Chem. A 1997, 101, 2358.
111. (b) Filatov, M.; Shaik, S. J. Phys. Chem. A 1998, 102, 3835.
112. Chen, G.; Espinosa-Perez, G.; Zentella-Dehesa, A.; Silaghi-Dumitrescu, I.; Lara-Ochoa, F. (Tetrakis(2-pyridylmethyl)ethylenediamine)iron(II) Perchlorate. Study of Density Functional Methods. Inorg. Chem. 2000, 39, 3440.
113. Maseras, F. Private communication.
114. Dapprich, S.; Komaromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. J. Mol. Struct.: THEOCHEM 1999, 461-462, 1.