Synthesis, crystal structure, and reactions of the 17-valence-electron rhenium methyl complex [(η5-C5Me5)Re(NO)(P(4-C6H 4CH3)3)(CH3)]•+ B(3,5-C6H3(CF3)2)- 4:

Journal of Organometallic Chemistry

Volumn 616, Issue 1-2, 2000, Pages 54-66

  Le Bras, Jean ^a   Jiao, Haijun ^a   Meyer, Wayne E ^b   Hampel, Frank ^a   Gladysz, J A ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

'Barf anion; Density functional calculation; Methylidene complex; Radical cation; Rhenium

Indexed keywords

EID: 0003036552     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00531-3     Document Type: Article

References (67)

1. D. Astruc, Electron Transfer and Radical Processes in Transition-Metal Chemistry, VCH, New York, 1995.
2. M.C. Baird, Chem. Rev. 88 (1988) 1217.
3. A recent leading reference: K. Costuas, J.-Y. Saillard, Organometallics 18 (1999) 2505.
4. 6: P. Legzdins, W.S. McNeil, R.J. Batchelor, F.W.B. Einstein, J. Am. Chem. Soc. 117 (1995) 10521.
5. 6: P. Legzdins, W.S. McNeil, R.J. Batchelor, F.W.B. Einstein, J. Am. Chem. Soc. 117 (1995) 10521.
6. 6: P. Legzdins, W.S. McNeil, R.J. Batchelor, F.W.B. Einstein, J. Am. Chem. Soc. 117 (1995) 10521.
7. 6: P. Legzdins, W.S. McNeil, R.J. Batchelor, F.W.B. Einstein, J. Am. Chem. Soc. 117 (1995) 10521.
8. 6: P. Legzdins, W.S. McNeil, R.J. Batchelor, F.W.B. Einstein, J. Am. Chem. Soc. 117 (1995) 10521.
9. 6: P. Legzdins, W.S. McNeil, R.J. Batchelor, F.W.B. Einstein, J. Am. Chem. Soc. 117 (1995) 10521.
10. •: L.S. Crocker, D.M. Heinekey, G.K. Schulte, J. Am. Chem. Soc. 111 (1989) 405. (c) There is also an extensive literature involving paramagnetic rhenium complexes in which the odd electron is ligand-centered: A. Klein, C. Vogler, W. Kaim, Organometallics 15 (1996) 236.
11. •: L.S. Crocker, D.M. Heinekey, G.K. Schulte, J. Am. Chem. Soc. 111 (1989) 405. (c) There is also an extensive literature involving paramagnetic rhenium complexes in which the odd electron is ligand-centered: A. Klein, C. Vogler, W. Kaim, Organometallics 15 (1996) 236.
12. •: L.S. Crocker, D.M. Heinekey, G.K. Schulte, J. Am. Chem. Soc. 111 (1989) 405. (c) There is also an extensive literature involving paramagnetic rhenium complexes in which the odd electron is ligand-centered: A. Klein, C. Vogler, W. Kaim, Organometallics 15 (1996) 236.
13. W.E. Meyer, A.J. Amoroso, M. Jaeger, J. Le Bras, W.-T. Wong, J.A. Gladysz, J. Organomet. Chem. 616 (2000) 44.
14. Full papers with extensive literature background: (a) W. Weng, T. Bartik, M. Brady, B. Bartik, J.A. Ramsden, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 117 (1995) 11922. (b) M. Brady, W. Weng, Y. Zhou, J.W. Seyler, A.J. Amoroso, A.M. Arif, M. Böhme, G. Frenking, J.A. Gladysz, J. Am. Chem. Soc. 119 (1997) 775. (c) S.B. Falloon, S. Szafert, A.M. Arif, J.A. Gladysz, Chem. Eur. J. 4 (1998) 1033. (d) T. Bartik, W. Weng, J.A. Ramsden, S. Szafert, S.B. Falloon, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 120 (1998) 11071. (e) R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J.A. Gladysz, J. Am. Chem. Soc. 122 (2000) 810.
15. Full papers with extensive literature background: (a) W. Weng, T. Bartik, M. Brady, B. Bartik, J.A. Ramsden, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 117 (1995) 11922. (b) M. Brady, W. Weng, Y. Zhou, J.W. Seyler, A.J. Amoroso, A.M. Arif, M. Böhme, G. Frenking, J.A. Gladysz, J. Am. Chem. Soc. 119 (1997) 775. (c) S.B. Falloon, S. Szafert, A.M. Arif, J.A. Gladysz, Chem. Eur. J. 4 (1998) 1033. (d) T. Bartik, W. Weng, J.A. Ramsden, S. Szafert, S.B. Falloon, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 120 (1998) 11071. (e) R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J.A. Gladysz, J. Am. Chem. Soc. 122 (2000) 810.
16. Full papers with extensive literature background: (a) W. Weng, T. Bartik, M. Brady, B. Bartik, J.A. Ramsden, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 117 (1995) 11922. (b) M. Brady, W. Weng, Y. Zhou, J.W. Seyler, A.J. Amoroso, A.M. Arif, M. Böhme, G. Frenking, J.A. Gladysz, J. Am. Chem. Soc. 119 (1997) 775. (c) S.B. Falloon, S. Szafert, A.M. Arif, J.A. Gladysz, Chem. Eur. J. 4 (1998) 1033. (d) T. Bartik, W. Weng, J.A. Ramsden, S. Szafert, S.B. Falloon, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 120 (1998) 11071. (e) R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J.A. Gladysz, J. Am. Chem. Soc. 122 (2000) 810.
17. Full papers with extensive literature background: (a) W. Weng, T. Bartik, M. Brady, B. Bartik, J.A. Ramsden, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 117 (1995) 11922. (b) M. Brady, W. Weng, Y. Zhou, J.W. Seyler, A.J. Amoroso, A.M. Arif, M. Böhme, G. Frenking, J.A. Gladysz, J. Am. Chem. Soc. 119 (1997) 775. (c) S.B. Falloon, S. Szafert, A.M. Arif, J.A. Gladysz, Chem. Eur. J. 4 (1998) 1033. (d) T. Bartik, W. Weng, J.A. Ramsden, S. Szafert, S.B. Falloon, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 120 (1998) 11071. (e) R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J.A. Gladysz, J. Am. Chem. Soc. 122 (2000) 810.
18. Full papers with extensive literature background: (a) W. Weng, T. Bartik, M. Brady, B. Bartik, J.A. Ramsden, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 117 (1995) 11922. (b) M. Brady, W. Weng, Y. Zhou, J.W. Seyler, A.J. Amoroso, A.M. Arif, M. Böhme, G. Frenking, J.A. Gladysz, J. Am. Chem. Soc. 119 (1997) 775. (c) S.B. Falloon, S. Szafert, A.M. Arif, J.A. Gladysz, Chem. Eur. J. 4 (1998) 1033. (d) T. Bartik, W. Weng, J.A. Ramsden, S. Szafert, S.B. Falloon, A.M. Arif, J.A. Gladysz, J. Am. Chem. Soc. 120 (1998) 11071. (e) R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J.A. Gladysz, J. Am. Chem. Soc. 122 (2000) 810.
19. 4.
20. (a) J. Huhmann-Vincent, B.L. Scott, G.J. Kubas, Inorg. Chem. 38 (1999) 115 and references therein.
21. (b) D.M. Heinekey, C.E. Radzewich, Organometallics 17 (1998) 51.
22. W.V. Konze, B.L. Scott, G.L. Kubas, Chem. Commun. (1999) 1807.
23. (a) F. Calderazzo, G. Pampaloni, L. Rocchi, U. Englert, Organometallics 13 (1994) 2592.
24. (b) I. Chávez, A. Alvarez-Carena, E. Molins, A. Roig, W. Maniukiewicz, A. Arancibia, H. Brand, J.M. Manríquez, J. Organomet. Chem. 601 (2000) 126.
25. M. Tilset, G.S. Bodner, D.R. Senn, J.A. Gladysz, V.D. Parker, J. Am. Chem. Soc. 109 (1987) 7551.
26. A.T. Patton, C.E. Strouse, C.B. Knobler, J.A. Gladysz, J. Am. Chem. Soc. 105 (1983) 5804.
27. Leading references to isolable methylidene complexes: J.L. Brumaghim, G.S. Girolami, Chem. Commun. (1999) 953.
28. S.R. Bahr, P. Boudjouk, J. Org. Chem. 57 (1992) 5545.
29. J. Sandström, Dynamic NMR Spectrometry, London, Academic Press, 1982 Chapters 6-7.
30. W. Weng, T. Bartik, M.T. Johnson, A.M. Arif, J.A. Gladysz, Organometallics 14 (1995) 889.
31. (a) P.J. Hay, W.R. Wadt, J. Chem. Phys. 82 (1985) 299.
32. (b) T.H. Dunning Jr., P.J. Hay, Modern Theoretical Chemistry, in: H.F. Scheafer III (Ed.), Plenum Press, New York, 1976. The double zeta basis set and a set of polarization function (DZp) for carbon (10s5p[3s/2p]721/41) with a polarization function (ζ = 0.6) and for hydrogen (4s[2s]/31). For phosphorus the pseudopotential (3s/3p[2s/2p]21/21) with a set of polarization function (ζ = 0.6). The basis set for rhenium required has the DZ quality {8s/6p/ 3d[3s/3p/2d]341/321/21) with (ζ = 0.073), and the (n-1)s and (n-l)p electrons were considered as part of the valence space.
33. GAUSSIAN-98, Revision A.5, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
34. For theory and applications: (a) W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, New York, 1986. (b) J.B. Foresman, Æ. Frisch, Exploring Chemistry with Electronic Structure Methods: A Guide to Using GAUSSIAN, Second Edition; Gaussian, Inc.: Pittsburgh PA, 1996.
35. For theory and applications: (a) W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, New York, 1986. (b) J.B. Foresman, Æ. Frisch, Exploring Chemistry with Electronic Structure Methods: A Guide to Using GAUSSIAN, Second Edition; Gaussian, Inc.: Pittsburgh PA, 1996.
36. (a) NBO Program, 3.1, E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold.
37. (b) A.E. Reed, L.A. Curtiss, F. Weinhold, Chem. Rev. 88 (1988) 899.
38. (a) W.A. Kiel, G.-Y. Lin, A.G. Constable, F.B. McCormick, C.E. Strouse, O. Eisenstein, J.A. Gladysz, J. Am. Chem. Soc. 104 (1982) 4865.
39. (b) S. Georgiou, J.A. Gladysz, Tetrahedron 42 (1986) 1109.
40. For other computational studies involving chiral rhenium complexes, see Ref. 7b and the following: (a) G.S. Bodner, A.T. Patton, D.E. Smith, S. Georgiou, W. Tam, W.-K. Wong, C.E. Strouse, J.A. Gladysz, Organometallics 6 (1987) 1954. (b) G.S. Bodner, D.E. Smith, W.G. Hatton, P.C. Heah, S. Georgiou, A.L. Rheingold, S.J. Geib, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 109 (1987) 7688. (c) W.E. Buhro, B.D. Zwick, S. Georgiou, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 110 (1988) 2427. (d) P.T. Czech, J.A. Gladysz, R.F. Fenske, Organometallics 8 (1989) 1806.
41. For other computational studies involving chiral rhenium complexes, see Ref. 7b and the following: (a) G.S. Bodner, A.T. Patton, D.E. Smith, S. Georgiou, W. Tam, W.-K. Wong, C.E. Strouse, J.A. Gladysz, Organometallics 6 (1987) 1954. (b) G.S. Bodner, D.E. Smith, W.G. Hatton, P.C. Heah, S. Georgiou, A.L. Rheingold, S.J. Geib, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 109 (1987) 7688. (c) W.E. Buhro, B.D. Zwick, S. Georgiou, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 110 (1988) 2427. (d) P.T. Czech, J.A. Gladysz, R.F. Fenske, Organometallics 8 (1989) 1806.
42. For other computational studies involving chiral rhenium complexes, see Ref. 7b and the following: (a) G.S. Bodner, A.T. Patton, D.E. Smith, S. Georgiou, W. Tam, W.-K. Wong, C.E. Strouse, J.A. Gladysz, Organometallics 6 (1987) 1954. (b) G.S. Bodner, D.E. Smith, W.G. Hatton, P.C. Heah, S. Georgiou, A.L. Rheingold, S.J. Geib, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 109 (1987) 7688. (c) W.E. Buhro, B.D. Zwick, S. Georgiou, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 110 (1988) 2427. (d) P.T. Czech, J.A. Gladysz, R.F. Fenske, Organometallics 8 (1989) 1806.
43. For other computational studies involving chiral rhenium complexes, see Ref. 7b and the following: (a) G.S. Bodner, A.T. Patton, D.E. Smith, S. Georgiou, W. Tam, W.-K. Wong, C.E. Strouse, J.A. Gladysz, Organometallics 6 (1987) 1954. (b) G.S. Bodner, D.E. Smith, W.G. Hatton, P.C. Heah, S. Georgiou, A.L. Rheingold, S.J. Geib, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 109 (1987) 7688. (c) W.E. Buhro, B.D. Zwick, S. Georgiou, J.P. Hutchinson, J.A. Gladysz, J. Am. Chem. Soc. 110 (1988) 2427. (d) P.T. Czech, J.A. Gladysz, R.F. Fenske, Organometallics 8 (1989) 1806.
44. R.F. Jordan, J.R. Norton, J. Am. Chem. Soc. 101 (1979) 4853.
45. (a) F.B. McCormick, R.J. Angelici, R.A. Pickering, R.E. Wagner, R.A. Jacobson, Inorg. Chem. 20 (1981) 4108.
46. 3 rotational barriers, see S.G. Davies, A.E. Derome, J.P. McNally, J. Am. Chem. Soc. 113 (1991) 2854, and references therein.
47. W.A. Kiel, G.-Y. Lin, G.S. Bodner, J.A. Gladysz, J. Am. Chem. Soc. 105 (1983) 4958.
48. L. Dahlenburg, A. Weiß, M. Bock, A. Zahl, J. Organomet. Chem. 541 (1997) 465.
49. S.G. Davies, I.M. Dordor-Hedgecock, K.H. Sutton, M. Whittaker, J. Am. Chem. Soc. 109 (1987) 5711.
50. A.G. Orpen, N.G. Connelly, J. Chem. Soc. Chem. Commun. (1985) 1310.
51. H. Jiao, Unpublished computations, University Erlangen-Nürnberg.
52. J.H. Merrifield, C.E. Strouse, J.A. Gladysz, Organometallics 1 (1982) 1204.
53. T.-S. Peng, A.M. Arif, J.A. Gladysz, J. Chem. Soc. Dalton Trans. (1995) 1857.
54. B.E.R. Schilling, R. Hoffmann, D.L. Lichtenberger, J. Am. Chem. Soc. 101 (1979) 585.
55. A.K. Rappé, W.A. Goddard, III, J. Am. Chem. Soc. 99 (1977) 3966.
56. G.L. Crocco, K.E. Lee, J.A. Gladysz, Organometallics 9 (1990) 2819.
57. B.E.R. Schilling, R. Hoffmann, J.W. Faller, J. Am. Chem. Soc. 101 (1979) 592.
58. H. Jiao, J.A. Gladysz, (in preparation).
59. (a) J.W. Hershberger, R.J. Klingler, J.K. Kochi, J. Am. Chem. Soc. 105 (1983) 61.
60. (b) N.N. Turaki, J.M. Huggins Organometallics 5 (1986) 1703.
61. (c) Y. Huang, G.B. Carpenter, D.A. Sweigart, Y.K Chung, B.Y. Lee, Organometallics 14 (1995) 1423, and references therein.
62. (a) D. Astruc, Acc. Chem. Res. 24 (1991) 36.
63. (b) P. Legzdins, W.S. McNeil, M.J. Shaw, Organometallics 13 (1994) 562.
64. G.S. Bodner, J.A. Gladysz, M.F. Nielsen, V.D. Parker, J. Am. Chem. Soc. 109 (1987) 1757.
65. W.E. Meyer, A.J. Amoroso, C.R. Horn, M. Jaeger, J.A. Gladysz, submitted to Organometallics.
66. M. Brookhart, B. Grant, A.F. Volpe, Jr., Organometallics 11 (1992) 3920.
67. G.M. Sheldrick, SHELXL-93, University of Göttingen, Göttingen, Germany, 1993.