A computational study of Grubbs-type catalysts: Structure and application in the degenerate metathesis of ethylene

Journal of Molecular Structure: THEOCHEM

Volumn 763, Issue 1-3, 2006, Pages 37-42

  Sabbagh, Ingrid T ^a   Kaye, Perry T ^a  

^a RHODES UNIVERSITY   (South Africa)

Author keywords

Density functional theory; Dmol3; Ethylene; Grubbs catalysts; Metathesis; Molecular mechanics; Semi empirical PM3

Indexed keywords

EID: 33646165914     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2006.01.014     Document Type: Article

References (33)

1. Schwab P., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 118 (1996) 100
2. Aagaard O.M., Meier R.J., and Buda F. J. Am. Chem. Soc. 120 (1998) 7174
3. Bernardi F., Bottoni A., and Miscione G.P. Organometallics 22 (2003) 940
4. Fomine S., Vargas S.M., and Tlenkopatchev M.A. Organometallics 22 (2003) 93
5. Cavallo L. J. Am. Chem. Soc. 124 (2002) 8965
6. Adlhart C., and Chen P. Angew. Chem. Int. Ed. 41 23 (2002) 4484
7. Adlhart C., and Chen P. J. Am. Chem. Soc. 126 (2004) 3496
8. See, for example. Hagemann J.P., and Kaye P.T. J. Chem. Soc., Perkin Trans. 1 (1999) 341-347
9. Daubinet A., and Kaye P.T. Synth. Commun. 32 20 (2002) 3207-3217
10. Kaye P.T., and Tshikhudo T.R. J. Chem. Res. (S) (2003) 179-181 (J. Chem. Res. (M) (2003) 0401-0418)
11. Kaye P.T., Gxoyiya B.S.B., and Hagemann J.P. J. Chem. Res. 4 (2004) 252-256
12. See, for example. Kaye P.T., Mphahlele M.J., and Brown M.E. J. Chem. Soc., Perkin Trans. 2 (1995) 835-838
13. Kaye P.T., and Robinson R.S. Tetrahedron 54 (1998) 13253-13256
14. Kaye P.T., Musa M.A., Nocanda X.N., and Robinson S. Org. Biomol. Chem. 1 (2003) 1133-1138
15. Delley B. J. Chem. Phys. 92 (1990) 508
16. Delley B. J. Phys. Chem. 100 (1996) 6107
17. Delley B. J. Chem. Phys. 113 (2000) 7756
18. 2®, Version 4.0.
19. Rappé A.K., Casewit C.J., Colwell K.S., Goddard W.A., and Skiff W.M. J. Am. Chem. Soc. 114 (1992) 10024
20. Rappé A.K., and Goddard W.A. J. Phys. Chem. 95 (1991) 3358
21. Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612.
22. Perdew J.P., and Wang Y. Phys. Rev. B 45 (1992) 13244
23. W. Kohn, L.J. Sham, Phys. Rev. 140 (1965) A1133.
24. Pulay P. J. Comput. Chem. 3 (1982) 556
25. Halgren T.A., and Lipscomb W.N. Chem. Phys. Lett. 49 (1977) 225
26. Henkelman G., and Jonsson H. J. Chem. Phys. 113 (2000) 9978
27. Schwab P., France M.B., Ziller J.W., and Grubbs R.H. Angew. Chem. Int. Ed. Engl. 34 (1995) 2039
28. Louie J., and Grubbs R.H. Organometallics 21 (2002) 2153
29. Nguyen S.T., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 115 (1993) 9858
30. Sanford M.S., Ulman M., and Grubbs R.H. J. Am. Chem. Soc. 123 (2001) 749
31. Depending on the starting MM-minimised structure, SE (PM3) calculations afforded distorted metallacycles exhibiting bonding of ruthenium to the benzylic proton or (at higher energy) to one of the methylene protons.
32. Vyboishchikov S.F., Bühl M., and Thiel W. Chem. Eur. J. 8 (2002) 3962
33. -1) vibrations (three for TS I and one for TS II) may well affect the accuracy of the corresponding free-energy calculations.