How important is metal - Ligand back-bonding toward YX3 ligands (Y = N, P, C, Si)? An NBO analysis

Organometallics

Volumn 26, Issue 10, 2007, Pages 2637-2645

  Leyssens, Tom ^a   Peeters, Daniel ^a   Orpen, A Guy ^b   Harvey, Jeremy N ^b  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; METALS; PHOSPHATES; PYRIDINE;

BACK-BONDING; BIPYRIDINE; PERTURBATIVE ENERGY; PHOSPHINE LIGANDS;

LIGANDS;

EID: 34249038299     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om061151z     Document Type: Article

References (79)

1. Simoes, J. A. M.; Beauchamp, J. L. Coord. Chem. Rev. 1990, 90, 629-688.
2. Franking, G.; Frohlich, N. Chem. Rev. 2000, 100, 717-774.
3. (a) Kuhl, O. Coord. Chem. Rev. 2005, 249, 693-704.
4. (b) Dias, P. B.; de Piedade, M. E. M.; Simoes, J. A. M. Coord. Chem. Rev. 1994, 135/ 136, 737-807.
5. (c) Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
6. Fey, N.; Tsipis, A. C.; Harris, S. E.; Harvey, J. N.; Orpen, A. G.; Mansson, R. A. Chem. - Eur. J. 2006, 12, 291-302.
7. Leyssens, T.; Peeters, D.; Orpen, A. G.; Harvey, J. N. New J. Chem. 2005, 29, 1424-1430.
8. (a) Orpen, A. G.; Connelly, N. G. J. Chem. Soc., Chem. Commun. 1985, 1310.
9. (b) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206.
10. (a) Xiao, S. X.; Trogler, W. C.; Ellis, D. E.; Berkovitch-Yellin, Z. J. Am. Chem. Soc. 1983, 105, 7033.
11. (b) Marynick, D. S. J. Am. Chem. Soc. 1984, 106, 4064.
12. (c) Tossell, J. A.; Moore, J. H.; Giordan, J. C. Inorg. Chem. 1985, 24, 1100.
13. Pacchioni, G.; Bagus, P. S. Inorg. Chem. 1992, 31, 4391-4398.
14. Van Wüllen, C. J. Comput. Chem. 1997, 18, 1985-1992.
15. Wovkulich, J. M.; Atwood, J. L.; Canada, L.; Atwood, J. D. Organometallics 1995, 4, 867-871.
16. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2953-2956.
17. Bodner, M. G.; May, M. P.; McKinney, L. E. Inorg. Chem. 1980, 19, 1951-1958.
18. Yarbrough, L. W.; Hall, M. B. Inorg. Chem. 1978, 17, 2269-2275.
19. (a) Rahman, M. M.; Liu, H.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1989, 8, 1-7.
20. (b) Rahman, M. M.; Liu, H.; Prock, A.; Giering, W. P. Organometallics 1987, 6, 650-658.
21. (e) Liu, H.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1990, 9, 1758-1766.
22. (d) Fernandez, A. L.; Wilson, M. R.; Prock, A.; Giering, W. P. Organometallics 2001, 20, 3429-3435.
23. Golovin, M. N.; Rahman, M. M.; Belmonte, J. E.; Giering, W. P. Organometallics 1985, 4, 1981-1991.
24. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1.
25. (b) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1558.
26. (c) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755.
27. Gonzalez-Blanco, O.; Branchadell, V. Organometallics 1997, 16, 5556-5562.
28. Frenking, G.; Wichmann, K.; Fröhlich, N.; Grobe, J.; Golla, W.; Le Van, D.; Krebs, B.; Läge, M. Organometallics 2002, 21, 2921-2930.
29. (a) Bagus, P. S.; Hermann, K.; Bauschlicher, C. W. J. Chem. Phys. 1984, 80, 4378.
30. (b) Bagus, P. S.; Hermann, K.; Bauschlicher, C. W. J. Chem. Phys. 1984, 81, 1966.
31. (c) Bauschlicher, C. W.; Bagus, P. S.; Nelin, C. J.; Roos, B. O. J. Chem. Phys. 1986, 85, 354.
32. (d) Hermann, K.; Bagus, P. S.; Bauschlicher, C. W. Phys. Rev. B 1985, 31, 6371.
33. (a) Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge U. Press, 2005.
34. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
35. (c) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
36. (d) A. E., Reed; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
37. (a) Kwon, O.; Sevin, F.; Mckee, M. L. J. Phys. Chem. A 2001, 105, 913-922.
38. (b) Can, H.; Zhan, D.; Balci, M; Brickmann, J. Eur. J. Org. Chem. 2003, 1111-1117.
39. (c) Monajjemi, M.; Chahkandi, B. J. Mol. Struct. (THEOCHEM) 2005, 714, 43-60.
40. To be found at http://www.chem.wisc.edu/~nbo5/tut_del.htm.
41. Weinhold, F. Angew. Chem., Int. Ed. 2003, 42, 4188-4194.
42. Sun, Q.; Li, Z.; Zeng, X.; Ge, M.; Wang, D. J. Mol. Struct. (THEOCHEM) 2005, 724, 155-161.
43. Sosa, G. L.; Peruchena, M.; Contreras, R. H.; Castro, E. A. J. Mol. Struct. (THEOCHEM) 2002, 577, 219-228.
44. Orian, L.; Ganis, P.; Santi, S.; Ceccon, A. J. Organomet. Chem. 2005, 090, 482-492.
45. Jesih, A.; Rahten, A.; Benkic, P.; Skapin, T.; Pejov, L.; Petrusevski, V. M. J. Solid State Chem. 2004, 177, 4482-4493.
46. Jaguar 5.0; Schrödinger, L.L.C.: Portland, OR, 1991-2003.
47. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 52, 270.
48. (a) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2 (1), 41-51.
49. (b) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322-328.
50. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
51. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
52. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
53. Maseras, F.; Morokuma, K. Chem. Phys. Lett. 1992, 195, 500-504.
54. (a) Landis, C. R.; Cleveland, T.; Firman, T. K. J. Am. Chem. Soc. 1995, 117, 1859-1860.
55. (b) Dobbs, K. D.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 4663-4664.
56. (c) Shen, M.; Schaefer, H. F.; Partridge, H. J. Chem. Phys. 1993, 98, 508-521.
57. (d) Langhoff, S. R.; Bausehlicher, C. W. Ann. Rev. Phys. Chem. 1988, 39, 181-212.
58. Landis, C. R.; Weinhold, F. J. Comput. Chem. 2006, 28, 198-203.
59. (a) Landis, C. R.; Firman, T. K.; Root, D. M.; Cleveland, T. J. Am. Chem. Soc. 1998, 120, 1842-1854.
60. (b) Firman, T. K.; Landis, C. R. J. Am. Chem. Soc. 1998, 120, 12650-12656.
61. (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422.
62. (b) Harvey, J. N.; Heslop, K. M.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2003, 278-179.
63. Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049.
64. Ruiz-Morales, Y.; Ziegler, T. J. Phys. Chem. A 1998, 102, 3970-3976.
65. Ernst, S.; Kurth, Y.; Kaim, W. J. Organomet. Chem. 1996, 302, 211-215.
66. 2 molecule.
67. King, W. A.; Di Bella, S.; Lanza, G.; Khan, K.; Duncalf, D. J.; Cloke, F. G. N.; Fragala, I. L.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 627-635.
68. Bennett, M. A.; Chee, H.; Jeffery, J. C.; Robertson, O. B. Inorg. Chem. 1979, 18, 1071.
69. Graham, W. A. G. Inorg. Chem. 1968, 7, 315-321.
70. Lichtenberger, D. L.; Rai-Chaudhuri, A. J. Am. Chem. Soc. 1991, 113, 2923-2930.
71. Choi, S.; Lin, Z. Organometallics 1999, 18, 5488-5495.
72. Lemke, F. R.; Galat, K. J.; Youngs, W. J. Organometallics 1999, 78, 1419-1429.
73. Hübler, K.; Hunt, P. A.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076-5083.
74. (a) Torrens, H. Coord. Chem. Rev. 2005, 249, 1957-1985.
75. (b) Kiplinger, J. L.; Richmond, T. G.; Ostetberg, C. E. Chem. Rev. 1994, 94, 373-431.
76. The bonding analysis for the cationic complexes is carried out at the same geometry as for the neutral species (see ref 5 for a discussion of the difference in their optimum geometries).
77. 3 complexes (about 20%).
78. The π interaction estimated by the ETS method in Table 6 includes both the π back-bonding to the ligand and π donation from the ligand to the metal. An increase in the latter could in principle account for the increase in the ETS π-bonding energy. However, on the basis of the NBO analysis, these latter interactions are not important.
79. Bartolotti, L. J.; Ayers, P. W. J. Phys. Chem. A 2005, 109, 1146.