Triphenyl-phosphine and -arsine analogues which facilitate the electrospray mass spectrometric analysis of neutral metal complexes

Abstract

The six triarylphosphines PPh_n(C₆H₄OMe-p)_3 – n and PPh_n(C₆H₄NMe₂-p)_3 – n(n = 0–3) and the arsine As(C₆H₄OMe-p)₃ (L) have been synthesized and examined for their use in the electrospray mass spectrometric (ESMS) study of metal complexes. This has been tested with selected examples of the complexes [Mo(CO)₄L₂], [Fe(CO)₃L₂], [Fe(CO)₄L], [Ru₃(CO)₉L₃], cis-[PtCl₂L₂], [PdCl₂L₂] and [AuCl(L)]. All of the metal carbonyl complexes of these ligands gave [M + H]⁺ ions in their spectra, while in contrast the analogous PPh₃ complexes do not, suggesting that these electrospray-friendly ligands should be useful for the characterisation of a wide range of complexes by ESMS. The incorporation of the ligands into metal halide complexes however does not allow the observation of [M + H]⁺ ions, with ions formed by the previously reported halide-loss mechanism being the only ones observed.

References

1. W. Henderson, B. K. Nicholson and L. J. McCaffrey, Polyhedron, 1998, 17, 4291; R. Colton, A. D'Agostino and J. C. Traeger, Mass Spectrom. Rev., 1995, 14, 79; C. E. C. A. Hop and R. Bakhtiar, J. Chem. Educ., 1996, 73, A162.
2. W. Henderson, J. S. McIndoe, B. K. Nicholson and P. J. Dyson, J. Chem. Soc., Dalton Trans., 1998, 519.
3. J. S. McIndoe and B. K. Nicholson, J. Organomet. Chem., 1999, 573, 232.
4. G. J. Van Berkel and F. Zhou, Anal. Chem., 1995, 67, 2916, 3958; A. Dupont, J.-P. Gisselbrecht, E. Leize, L. Wagner and A. Van Dorsselaer, Tetrahedron Lett., 1994, 35, 6083; C. E. C. A. Hop, D. A. Saulys and D. F. Gaines, J. Am. Soc. Mass Spectrom., 1995, 6, 860; A. T. Blades, M. G. Ikonomou and P. Kebarle, Anal. Chem., 1991, 63, 2109; X. Xu, S. P. Nolan and R. B. Cole, Anal. Chem., 1994, 66, 119.
5. W. Henderson, J. Fawcett, R. D. W. Kemmitt, P. McKenna and D. R. Russell, Polyhedron, 1997, 16, 2455; J. Fawcett, W. Henderson, R. D. W. Kemmitt, D. R. Russell and A. Upreti, J. Chem. Soc., Dalton Trans., 1996, 1897.
6. W. Henderson and C. Evans, Inorg. Chim. Acta, 1999, in press and refs. therein.
7. For selected reviews see: M. C. Simpson and D. J. Cole-Hamilton, Coord. Chem. Rev., 1996, 155, 163; B. Cornils and E. G. Kuntz, J. Organomet. Chem., 1995, 502, 177; P. Kalck and F. Monteil, Adv. Organomet. Chem., 1992, 34, 219; W. A. Herrmann and C. W. Kohlpaintner, Angew. Chem., Int. Ed. Engl., 1993, 32, 1524; Advanced Inorganic Chemistry, eds. F. A. Cotton, G. Wilkinson, C. A. Murillo and M. Bochmann, 6th edn., Wiley, New York, 1999.
8. S. J. Berners-Price and P. J. Sadler, Chem. Br., 1987, 541.
9. G. J. Van Berkel, J. M. E. Quirke, R. A. Tigani, A. S. Dilley and T. R. Covey, Anal. Chem., 1998, 70, 1544.
10. K. Yoshino, T. Takao, H. Murata and Y. Shimonishi, Anal. Chem., 1995, 67, 4028.
11. A. O. Aliprantis and J. W. Canary, J. Am. Chem. Soc., 1994, 116, 6985.
12. N. R. Champness and W. Levason, Coord. Chem. Rev., 1994, 133, 115.
13. T. L. Brown and K. J. Lee, Coord. Chem. Rev., 1993, 128, 89.
14. M. M. Rahman, H.-Y. Liu, K. Eriks, A. Prock and W. P. Giering, Organometallics, 1989, 8, 1 and refs. therein.
15. R. H. Laitinen, H. Riihimäki, M. Haukka, S. Jääskeläinen, T. A. Pakkanen and J. Pursiainen, Eur. J. Inorg. Chem., 1999, 1253.
16. R. Saf, C. Mirtl and K. Hummel, Tetrahedron Lett., 1994, 35, 6653.
17. R. Colton, K. L. Harrison, Y. A. Mah and J. C. Traeger, Inorg. Chim. Acta, 1995, 231, 65; W. Henderson and B. K. Nicholson, unpublished work.
18. L. J. Arnold, J. Chem. Educ., 1992, 69, 811.
19. G. P. Schiemenz, Liebigs Ann. Chem., 1971, 752, 30.
20. H. A. Brune, M. Falck, R. Hemmer and G. Schmidtberg, Chem. Ber., 1984, 117, 2791.
21. G. P. Schiemenz, Chem. Ber., 1965, 98, 65.
22. D. J. Darensbourg and R. L. Kump, Inorg. Chem., 1978, 17, 2680.
23. R. L. Keiter, E. A. Keiter, C. A. Boecker, D. R. Miller and K. H. Hecker, Inorg. Synth., 1997, 31, 210.
24. M. I. Bruce, G. Shaw and F. G. A. Stone, J. Chem. Soc., Dalton Trans., 1972, 2094.
25. Synthetic Methods of Organometallic and Inorganic Chemistry, Transition Metals Part 1, Georg Thieme Verlag, Stuttgart, New York, 1997, vol. 1, p. 170.
26. J. X. McDermott, J. F. White and G. M. Whitesides, J. Am. Chem. Soc., 1976, 98, 6521.
27. D. Drew and J. R. Doyle, Inorg. Synth., 1972, 13, 52.
28. G. K. Anderson, H. C. Clark and J. A. Davies, Inorg. Chem., 1981, 20, 3607.
29. B. P. Block, Inorg. Synth., 1953, 4, 15.
30. H. Inoue, T. Takei, G. Heckmann and E. Fluck, Z. Naturforsch., Teil B, 1991, 46, 682; C. Li and S. P. Nolan, Organometallics, 1995, 14, 1327.
31. V. K. Polovnyak, V. S. Slobodina, V. V. Kormachev and N. S. Akhmetov, Zh. Neorg. Khim., 1983, 28, 168.
32. H. Schmidbaur, B. Brachthauser, S. Gamper, A. Schier and O. Steigelmann, Z. Naturforsch., 1992, 47, 1725.