Intrinsic aptitude of cationic methyl- and ethylpalladium to associate ethylene and to further undergo subsequent migratory insertion. A theoretical study

Organometallics

Volumn 15, Issue 26, 1996, Pages 5542-5550

  Siegbahn, Per E M ^a   Strömberg, Staffan ^b   Zetterberg, Krister ^b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001111590     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9602973     Document Type: Article

References (67)

1. Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137.
2. Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
3. (a) Cossee, P. J. Catal. 1964, 3, 80.
4. (b) Arlman, E. J.; Cossee, P. J. Catal. 1964, 3, 99.
5. (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
6. (d) Jordan, R. F. J. Chem. Educ. 1988, 65, 285.
7. (e) Thomas, B. J.; Noh, S. K.; Schulte, G. K.; Schendlinger, S. C.; Theopold, K. H. J. Am. Chem. Soc. 1991, 113, 893.
8. (a) Keim, W.; Behr, A.; Roper, M. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, Chapter 52.
9. (b) Keim, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 235.
10. (c) Keim, W. J. Mol. Catal. 1989, 52, 19.
11. (d) Peuckert, M.; Keim, W. Organometallics 1983, 2, 594.
12. (e) Al-Jarallah, A. M.; Anabtawi, J. A.; Siddiqui, M. A. B.; Aitani, A. M.; Al-Sa'doun, A. W. Catal. Today 1992, 14, 1.
13. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987; p 724.
14. (b) Ritter, K. Synthesis 1993, 8, 735.
15. (c) Portnoy, M.; Ben-David, Y.; Rousso. I.; Milstein, D. Organometallics 1994, 13, 3465.
16. (d) Brown, J. M.; Pérez-Torrente, J. J.; Alcock, N. W.; Clase, H. J. Organometallics 1983, 14, 207.
17. (a) Reference 5a, p 389.
18. (b) Spencer. M. D.; Morse, P. M.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1993, 115, 2057.
19. (c) Casey, C. P.; Hallenbeck, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770.
20. For two leading references see: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443. (b) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394.
21. For two leading references see: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443. (b) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394.
22. (a) A (π-alkene)(σ-alkyl)cobalt species has been detected in a living homogeneous polymerization catalyst: Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M. J. Am. Chem. Soc. 1990, 112, 5634.
23. 2
24. (a) Strömberg, S.; Oksman, M.; Zhang, L.; Zetterberg, K. Acta Chem. Scand. 1995, 49, 689.
25. (b) De Felice, V.; Cucciolito, M. E.; De Renzi, A.; Ruffo, F.; Tesauro, D. J. Organomet. Chem. 1995, 493, 269.
26. Recent calculations show polymerization with weak precoordination of ethylene to Ti: (a) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (b) Jensen, R. V.; Børve, K. J.; Ystenes, M. J. Am. Chem. Soc. 1995, 117, 4109. Stronger precoordination has also been calculated: (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746.
27. Recent calculations show polymerization with weak precoordination of ethylene to Ti: (a) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (b) Jensen, R. V.; Børve, K. J.; Ystenes, M. J. Am. Chem. Soc. 1995, 117, 4109. Stronger precoordination has also been calculated: (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746.
28. Recent calculations show polymerization with weak precoordination of ethylene to Ti: (a) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (b) Jensen, R. V.; Børve, K. J.; Ystenes, M. J. Am. Chem. Soc. 1995, 117, 4109. Stronger precoordination has also been calculated: (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746.
29. It is well accepted that π-back-donation to an alkene is unfavorable for alkyl insertion. However, this circumstance does not suffice to discriminate against the transition metals to the right in the periodic table, as π-back-contribution is less important for e.g. palladium(II) and silver(I): (a) Ban, E. M.; Hughes, R. P.; Powell, J. J. Chem. Soc., Chem. Commun. 1973, 16, 591. (b) Partenheimer, W.; Durham, B. J. Am. Chem. Soc. 1974, 96, 3800. (c) Isolated cationic alkene complexes of e.g. Ni(II), Pd(II), Pt(II), Rh(III), Fe(II), Ru(II), and Os(II) undergo nucleophilic attack. In these cases there is not "any significant back donation". Bäckvall, J. E. In Reaction of Coordinated Ligands; Braterman, P. S., Ed.; Plenum Press: New York, 1986; Vol. 1, p 679.
30. It is well accepted that π-back-donation to an alkene is unfavorable for alkyl insertion. However, this circumstance does not suffice to discriminate against the transition metals to the right in the periodic table, as π-back-contribution is less important for e.g. palladium(II) and silver(I): (a) Ban, E. M.; Hughes, R. P.; Powell, J. J. Chem. Soc., Chem. Commun. 1973, 16, 591. (b) Partenheimer, W.; Durham, B. J. Am. Chem. Soc. 1974, 96, 3800. (c) Isolated cationic alkene complexes of e.g. Ni(II), Pd(II), Pt(II), Rh(III), Fe(II), Ru(II), and Os(II) undergo nucleophilic attack. In these cases there is not "any significant back donation". Bäckvall, J. E. In Reaction of Coordinated Ligands; Braterman, P. S., Ed.; Plenum Press: New York, 1986; Vol. 1, p 679.
31. It is well accepted that π-back-donation to an alkene is unfavorable for alkyl insertion. However, this circumstance does not suffice to discriminate against the transition metals to the right in the periodic table, as π-back-contribution is less important for e.g. palladium(II) and silver(I): (a) Ban, E. M.; Hughes, R. P.; Powell, J. J. Chem. Soc., Chem. Commun. 1973, 16, 591. (b) Partenheimer, W.; Durham, B. J. Am. Chem. Soc. 1974, 96, 3800. (c) Isolated cationic alkene complexes of e.g. Ni(II), Pd(II), Pt(II), Rh(III), Fe(II), Ru(II), and Os(II) undergo nucleophilic attack. In these cases there is not "any significant back donation". Bäckvall, J. E. In Reaction of Coordinated Ligands; Braterman, P. S., Ed.; Plenum Press: New York, 1986; Vol. 1, p 679.
32. For rhodium see: (a) Wang, L.; Flood, T. C. J. Am. Chem. Soc. 1992, 114, 3169. (b) Wang, L.; Lu, R. S.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999. For palladium see: (c) Reference 2.
33. For rhodium see: (a) Wang, L.; Flood, T. C. J. Am. Chem. Soc. 1992, 114, 3169. (b) Wang, L.; Lu, R. S.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999. For palladium see: (c) Reference 2.
34. For rhodium see: (a) Wang, L.; Flood, T. C. J. Am. Chem. Soc. 1992, 114, 3169. (b) Wang, L.; Lu, R. S.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999. For palladium see: (c) Reference 2.
35. (a) Becke, A. D. Phys. Rev. 1988, A38, 3098.
36. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
37. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
38. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
39. Vosko, S. H.; Wilk, L;. Nusair, M. Can. J. Phys. 1980, 58, 1200.
40. (a) Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
41. (b) Perdew, J. P. In Electronic Structure of Solids; Ziesche, P., Eischrig, H., Eds.; Akademie Verlag: Berlin, 1991.
42. (c) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. H.; Fiolhais, C. Phys. Rev. B 1992, 46, 6671.
43. Pople, J. A.; Head-Gordon, J. A.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622.
44. (a) Ricca, A.; Bauschlicher, C. W. Chem. Phys. Lett. 1995, 245, 150.
45. (b) Siegbahn, P. E. M. Adv. Chem. Phys., in press.
46. (c) Ricca, A.; Bauschlicher, C. W. J. Phys. Chem. 1994, 98, 12899.
47. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Reploge, E. S.; Gomperts, R.; Andres, J. L.; Ragavachari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. GAUSSIAN 92/DFT, Revision G.1; Gaussian, Inc., Pittsburgh, PA, 1993.
48. (a) Siegbahn, P. E. M.; Blomberg, M. R. A.; Svensson, M. Chem. Phys. Lett. 1994, 223, 35.
49. (b) Siegbahn, P. E. M.; Svensson, M.; Boussard, P. J. E. J. Chem. Phys. 1995, 102, 5377.
50. Chong, D. P.; Langhoff, S. R. J. Chem. Phys. 1986, 84, 5606.
51. Martin, R. L. J. Phys. Chem. 1983, 87, 750. See also: Cowan, R. D.; Griffin, D. C. J. Opt. Soc. Am. 1976, 66, 1010.
52. Martin, R. L. J. Phys. Chem. 1983, 87, 750. See also: Cowan, R. D.; Griffin, D. C. J. Opt. Soc. Am. 1976, 66, 1010.
53. STOCKHOLM is a general purpose quantum-chemical set of programs written by: P. E. M. Siegbahn, M. R. A. Blomberg, L. G. M. Pettersson, B. O. Roos, and J. Almlöf.
54. Huzinaga, S. J. Chem. Phys. 1965, 42, 1293.
55. Huzinaga, S. J. Chem. Phys. 1977, 66, 4245.
56. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
57. 3)(ethylene) shows no exchange with free ethylene in solution on the NMR time scale at 23°C as reported by: Kurosawa, H.; Majima, T.; Asada, N. J. Am. Chem. Soc. 1980, 102, 6996. This suggests a bond dissociation energy above ∼15.0 kcal/mol. The solution of the same complex tolerates storage at room temperature for days but decomposes rapidly at +50°C. If the decomposition is initiated by loss of ethylene, this would correspond to a bond dissociation energy in the area suggested.
58. 3)(ethylene) shows no exchange with free ethylene in solution on the NMR time scale at 23°C as reported by: Kurosawa, H.; Majima, T.; Asada, N. J. Am. Chem. Soc. 1980, 102, 6996. This suggests a bond dissociation energy above ∼15.0 kcal/mol. The solution of the same complex tolerates storage at room temperature for days but decomposes rapidly at +50°C. If the decomposition is initiated by loss of ethylene, this would correspond to a bond dissociation energy in the area suggested.
59. Åkermark, B.; Bäckvall, J.-E.; Hegedus, L. S.; Siirala-Hanse'n, K.; Sjöberg, K.; Zetterberg, K. J. Organomet. Chem. 1974, 72, 127.
60. Ziegler, T.; Tschinke, V. Bonding Energetics in Organometallic Compounds; ACS Symposium Series 428; Marks, T. J., Ed.; American Chemical Society: Washington, DC, 1990; p 284.
61. Sini, G.; Macgregor, S. A.; Eisenstein, O.; Teuben, J. H. Organometallics 1994, 13, 1049.
62. Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147.
63. Åkermark, B.; Glaser, J.; Öhrström, L.; Zetterberg, K. Organometallics 1991, 10, 733.
64. Examples of N-Pd-N angles: (a) De Felice, V.; Albano, V. G.; Castellari, C.; Cucciolito, M. E.; De Renzi, A. J. Organomet. Chem. 1991, 403, 269. (b) Albano, V. G.; Castellari, C.; Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269.
65. Examples of N-Pd-N angles: (a) De Felice, V.; Albano, V. G.; Castellari, C.; Cucciolito, M. E.; De Renzi, A. J. Organomet. Chem. 1991, 403, 269. (b) Albano, V. G.; Castellari, C.; Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269.
66. (a) Zang, L.; Zetterberg, K. Organometallics 1991, 10, 3806.
67. (b) Arnek, R.; Zetterberg, K. Organometallics 1987, 6, 1230.