Ab Initio MO Study of Palladium-Assisted Nucleophilic Attack on a Coordinated Olefin: Semiquantitative Understanding of the Reaction and the Mechanism of Palladium Acceleration

Inorganic Chemistry

Volumn 26, Issue 15, 1987, Pages 2499-2505

  Sakaki, Shigeyoshi ^a   Maruta, Katsuhiko ^a   Ohkubo, Katsutoshi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000192259     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic00262a032     Document Type: Article

References (18)

1. The following review articles have been published concerning this issue: Davies, S. G.; Green, M. L. H.; Mingos, D. M. P. Tetrahedron 1978, 34, 3047. Houghton, R. P. Metal Complexes in Organic Chemistry, Cambridge University Press: Cambridge, England, 1979; Chapter 4.
2. Hartley, F. R. The Chemistry of Platinum and Palladium: Applied Science: London, 1973. Trost, B. M. Tetrahedron 1977, 33, 2615. Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic: New York, 1978; Chapter 5. Heck, R. F. Acc. Chem. Res. 1979, 12. 146. Bäckvall. J. E. Tetrahedron 1983. 16. 335.
3. Sakaki, S.; Nishikawa, M.; Ohyoshi, A. J. Am. Chem. Soc. 1980, 102, 4062. Einsenstein, O.; Hoffmann, R. Applied Science 1980, 102, 6148; 1981, 103, 4308. Backvall, J. E.; Björkman, E. E.; Petterson, L.; Siegbahn, P. Applied Science 1984.,106, 4369; 1985, 107, 7265. Fujimoto, H.; Yamasaki, T. Applied Science 1986, 108,578. Sakaki, S.; Maruta, K.; Ohkubo, K. J. Chem. Soc., Dalton Trans. 1987. 361.
4. ÅKermark, B.; Backvall, J. E.; Siirala-Hansen, K.; Sjoberg, K.; Zetterberg, K. Tetrahedron Lett. 1974, 1363. Âkermark, B.; Bäckvall, J. E. J. Chem. Soc. Dalton Trans. 1975, 819. Hegedus, L. S.; Siirala-Hansén, K. J. Am. Chem. Soc. 1975, 97, 1184. Bäckvall, B. Tetrahedron Lett. 1978, 163. Bäckvall, J. E.; Bjorkman, E. E. J. Org. Chem. 1980, 45, 2893. Backvall, J. E.; Björkman, E. E.; Bystrom, S. E. Tetra hedron Lett. 1982, 943. Backvall, J. E.; Byrstrom, S. E. J. Org. Chem. 1982, 47, 1126.
5. Hayashi, T.; Hegedus, L. S. J. Am. Chem. Soc. 1977, 99, 7093. Murahashi, S.; Yamamura, M.; Mita, N. J. Org. Chem. 1977, 42, 2870. Hegedus, L. S.; Hayashi, T.; Darlington, W. H. J. Am. Chem. Soc. 1978,100,7747. Kurosawa, H.; Asada, N. Tetrahedron Lett. 1979, 255. Hegedus, L. S.; Williams, R. E.; McGuire, M. A.; Hayashi, T. J. Am. Chem. Soc. 1980, 102, 4973.
6. Henry, P. M. Acc. Chem. Res. 1973, 6, 16; J. Am. Chem. Soc. 1972, 94, 7305; J. Org. Chem. 1967, 32, 2575; 1973, 38, 1681; 1974, 39, 3871. Still, J. K.; James, D. E.; Hines, L. F. J. Am. Chem. Soc. 1973, 95, 5062. Backvall, J. E. J. Chem. Soc., Chem. Commun. 1977, 413. Backvall, J. E.; Akermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411. Kurosawa, H.; Majima, T.; Asada, N. J. Am. Chem. Soc. 1980, 102, 6996.
7. Morokuma, K.; Kato, S.; Kitaura, K.; Ohmine, I.; Sakai, S.; Obara, S. IMS Computer Center Program Library; Institute for Molecular Science: Okazaki. Japan, 1980; No. 0372.
8. Binkley, J. S.; Frisch, M. J.; DeFrees, D. J.; Raghavachari, K.; Whiteside, R. A.; Schlegel, H. B.; Pople, J. A. Gaussian 82; Carnegie-Mellon Chemistry Publishing Unit: Pittsburgh, PA, 1984.
9. Sakai, Y.; Tatewaki, H.; Huzinaga S. J. Comput. Chem. 1982, 3, 6. Tatewaki, H.; Huzinaga, S. Carnegie-Mellon Chemistry Publishing Unit 1980, 1, 205. For the hydrogen atom, the split-valence basis set proposed by Huzinaga-Dun-ning was used: Dunning, T. H.; Hay, P. J. In Method of Electronic Structure Theory; Schaeffer, H. F., Ed.; Plenum: New York, 1977.
10. Hehre, W. J.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1969, 51, 2657. Hehre, W. J.; Ditchfield, R.; Stewart, R. F.; Pople, J. A. J. Comput. Chem. 1970, 52, 2769.
11. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939, Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Pietro, W. J.; Hehre, W. J. J. Chem. Phys. 1982, 104, 2797. In [PdF(PH3)2(C2H4)]+, the Pd—PH3 distance was taken from the experimental structure of a similar complex: Ferguson, G.; McCrindle, R.; McAlees, A. J.; Parvez, M. Acta Crystallogr., Sect. B:Struct. Crystallogr. Cryst. Chem. 1982, B38, 3679.
12. Dempsey, J. N.; Baenziger, N. C. J. Am. Chem. Soc. 1955, 77, 4984.
13. Hay, P. J. J. Am. Chem. Soc. 1981, 103, 1390.
14. Morokuma, K. Acc. Chem. Res. 1977, 10, 294. Kitaura, K.; Morokuma, K. Int. J. Quantum Chem. 1976, 10, 325. Kitaura, K.; Sakaki, S.; Morokuma, K. Inorg. Chem. 1981, 10, 2292.
15. Sutton, L. E., Ed. Spec. Publ.—Chem. Soc. 1965, No. 18.
16. Similar orbital mixing has been proposed for the organic reactions20band the reactions of non transition metals.3e Bach, R. D.; Wolber, G. J. Am. Chem. Soc. 1984, 106 1401.
17. Calderazzo, F.; Dell'Amico D. B. Inorg. Chem. 1981, 20, 1310. Uson R.; Forniès J.; Tomas, M.; Menjón, B. Organometallics 1985, 4, 1912
18. The BSSE value was estimated by the counterpoise method: Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553. Ostlund, N. S.; Merrifield, D. L. Chem. Phys. Lett. 1976, 39, 612.