Neutral organometallic palladium(II) aquo complexes

Organometallics

Volumn 21, Issue 17, 2002, Pages 3536-3543

  Bartolomé, Camino ^a   Espinet, Pablo ^a   Vicente, Laura ^a   Villafañe, Fernando ^a   Charmant, Jonathan P H ^b   Orpen, A Guy ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; HYDROLYSIS; PALLADIUM; X RAY DIFFRACTION ANALYSIS;

AQUO LIGANDS;

ORGANOMETALLICS;

EID: 0012739904     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020198r     Document Type: Article

References (90)

1. Edelmann, F. T. Comments Inorg. Chem. 1992, 12, 259.
2. (a) Stalke, D.; Whitmire, K. H. Chem. Commun. 1990, 833.
3. (b) Brooker, S.; Buijink, J.-K.; Edelman, F. T. Chem. Commun. 1991, 10, 25.
4. (c) Grützmacher, H.; Pritzkow, H.; Edelmann, F. T. Organometallics 1991, 10, 23.
5. (d) Whitmire, K. H.; Labahn, D.; Roesky, H. W.; Noltemeyer, M.; Sheldrick, G. M. J. Organomet. Chem. 1991, 402, 55.
6. (e) Lay, U.; Pritzkow, H.; Grützmacher, H. Chem. Commun 1992, 260.
7. (f) Brooker, S.; Bertel, N.; Stalke, D.; Noltemeyer, M.; Roesky, H. W.; Sheldrick, G. M.; Edelmann, F. T. Organometallics 1992, 11, 192.
8. (g) Schulter, R. D.; Cowley, A. H.; Atwood, D.A.; Jones, R. A.; Bond, M. R.; Carrano, C. J. J. Am. Chem. Soc. 1993, 115, 2070.
9. (h) Schulter, R. D.; Isom, H.S.; Cowley, A. H.; Atwood, D. A.; Jones, R. A.; Olbrich, F.; Corbelin, S.; Lagow, R. J. Organometallics 1994, 263, 4058.
10. (i) Vij, A.; Kirchmeier, R. L.; Willett, R. D.; Shreeve, J. M. Inorg. Chem. 1994, 33, 5456.
11. (j) Ahlemann, J.-T.; Künzel, A.; Roesky, H. W.; Noltemeyer, M.; Markovskii, L.; Schmidt, H.-G. Inorg. Chem. 1996, 35, 6644.
12. (k) Bender, J. E., IV; Holl, M. M. B.; Kampf, J. W. Organometallics 1997, 16, 2743.
13. (l) Bender, J. E., IV; Holl, M. M. B.; Mitchell, A.; Wells, N. J.; Kampf, J. W. Organometallics 1998, 17, 5166.
14. (m) Klinkhammer, K. W.; Fässler, T. F.; Grützmacher, H. Angew. Chem., Int. Ed. 1998, 37, 124.
15. (n) Bender, J. E., IV; Shusterman, A. J.; Holl, M. M. B.; Kampf, J. W. Organometallics 1999, 18, 1547.
16. (o) Burford, N.; Macdonald, C. L. B.; LeBlanc, D. J.; Cameron T. S. Organometallics 2000, 19, 152.
17. (a) Belay, M.; Edelmann, P. T. J. Organomet. Chem. 1994, 479, C21.
18. (b) Gibson, V. C.; Redshaw, C.; Sequeira, L. J.; Dillon, K. B.; Clegg, W.; Elsegood, M. R. J. Chem. Commun. 1996, 2151.
19. (c) Dillon, K. B.; Gibson, V. C.; Howard, J. A. K.; Redshaw, C.; Sequeira, L.; Yao, J. W. J. Organomet. Chem 1997, 528, 179.
20. (d) Espinet, P.; Martín-Barrios, S.; Villafañe, F.; Jones, P. G. Organometallics 2000, 19, 290.
21. (e) Batsanov, A. S.; Dillon, K. B.; Gibson, V. C.; Howard, J. A. K.; Sequeira, L.; Yao, J. W. J. Organomet. Chem. 2001, 631, 181.
22. (f) Benedikt, G. M.; Goodall, B. L.; Iyer, S.; McIntosh, L. H., III; Mimna, R.; Rhodes, L. F.; Day, C. S.; Day, V. W. Organometallics 2001, 20, 2565.
23. Bartolomé, C.; Espinet, P.; Villafañe, P.; Giesa, S.; Martín, A.; Orpen, A. G. Organometallics 1996, 15, 2019.
24. Bariolomé, C.; de Blas, R.; Espinet, P.; Martín-Álvarez, J. M.; Villafañe, F. Angew. Chem., Int. Ed. 2001, 40, 2521.
25. Voelker, H.; Labahn, D.; Bohnen, F. M.; Herbst-Irmer, R.; Roesky, H. W.; Stalke, D.; Edelmann, P. T. New J. Chem. 1999, 23, 905.
26. Meyer, E. M.; Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Organometallics 1989, 8, 1079.
27. (a) Usón, R.; Forniés, J.; Tomás, M.; Casas, J. M.; Navarro, R. J. Chem. Soc., Dalton Trans. 1989, 169.
28. (b) Usón, R.; Forniés, J.; Tomás, M.; Casas, J. M.; Cotton, F. A.; Falvello, L. R.; Llusar, R. Organometallics 1988, 7, 2279.
29. (c) Albéniz, A. C.; Espinet, P.; Martín-Ruiz, B. Chem. Eur. J. 2001, 7, 2481.
30. Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031.
31. (a) Muharashi, S. I.; Tamba, Y.; Yamamura, M.; Moritani, I. Tetrahedron Lett. 1974, 3749.
32. (b) Muharashi, S. I.; Tamba, Y.; Yamamura, M.; Yoshimura, N. J. Org. Chem. 1978, 43, 4099.
33. Crystal structures of cationic organometallic palladium aquo complexes: (a) Deeming, A. J.; Rothwell, I. P.; Hursthouse, M. B.; New, L. J. Chem. Soc., Dalton Trans. 1978, 1490.
34. (b) Castan, P.; Jaud, P.; Wimmer, S.; Wimmer, F. L. J. Chem. Soc., Dalton Trans. 1991, 1155.
35. (c) Vicente, J.; Arcas, A.; Borrachero, M. V.; Molíns, E.; Miratvilles, C. J. Organomet. Chem. 1992, 441, 487.
36. (d) Sheehan, J. P.; Spalding, T. R.; Ferguson, G.; Gallagher, J. P.; Kaitner, B.; Kennedy, J. D. J. Chem. Soc., Dalton Trans. 1993, 35.
37. (e) Seligson, A. L.; Trogler, W. C. Organometallics 1993, 12, 738.
38. (f) Maassarani, F.; Davidson, M. F.; Wehman-Ooyevaar, I. C. M.; Grove, D. M.; van Koten, M. A.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Inorg. Chim. Acta 1995, 235, 327.
39. (g) Vicente, J.; Arcas, A.; Bautista, D. Organometallics 1997, 16, 2127.
40. (h) Vicente, J.; Arcas, A.; Blasco, M. A.; Lozano, J.; Ramírez de Arellano, M. C. Organometallics 1998, 17, 5374.
41. (i) Ruiz, J.; Florenciano, F.; Vicente, C.; Ramírez de Arellano, M. C.; López, G. Inorg. Chem. Commun. 2000, 3, 73.
42. (j) Barco, I. C.; Falvello, L. R.; Fernández, S.; Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1998, 1699.
43. (k) Ma, J.-F.; Kojima, Y.; Yamamoto, Y. J. Organomet. Chem. 2000, 616, 149.
44. Other cationic palladium organometallic aquo complexes reported but not characterized by diffraction methods: (l) Ryabov, A. D.; Kazankov, G. M.; Yatsimirsky, A. K.; Kuz'mina, L. G.; Burtseva, O. Y.; Dvortsova, N. V.; Polyakov, V. A. Inorg. Chem. 1992, 31, 3083.
45. Crystal structures of cationic coordination palladium aquo complexes: (m) Leoni, P.; Sommovigo, M.; Pasquali, M.; Midollini, S.; Braga, D.; Sabatino, P. Organometallics 1991, 10, 1038.
46. (n) Stang, P. J.; Cao, D. H.; Poulter, G. T.; Arif, A. T. Organometallics 1998, 14, 1110.
47. Other cationic palladium coordination aquo complexes reported but not characterized by diffraction methods: (o) Fuss, M.; Siehl, H. U.; Olenyuk, B.; Stang, P. J. Organometallics 1999, 18, 758.
48. 2, L being the orthometalated N′-methyl-2,2′-dipyridinium cation, should be considered an essentially neutral Pd aquo complex, since the positive charge must be associated to the methylated nitrogen. Note that the second anionic ligand (nitrate) is a very poor hard donor, which renders the Pd center much harder than ours. Also the positive nitrogen in the heterocycle will still be more electron attracting than a neutral carbon atom and will make the protonated hydrocarbyl harder than a phenyl. Whether neutral or cationic, this must be a rather hard Pd center for which coordination of a hard ligand is not unnatural. Our case is different and remarkable because of the softness of the center where water coordinates.
49. Espinet, P.; Martínez-Ilarduya, J. M.; Pérez-Briso, C.; Casado, A. L.; Alonso, M. A. J. Organomet. Chem. 1998, 551, 9.
50. Although the covalent radii of fluorine (58 pm) and hydrogen (30 pm) differ, their van der Waals radii are similar: 135 vs 120 pm, respectively: Emsley, J. The Elements, 2nd ed.; Oxford University Press: Oxford, 1991.
51. Falvello, L. R.; Forniés, J.; Navarro, R.; Sicilia, V.; Tomás, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891.
52. Kubas, G. J.; Burns, C. J.; Khalsa, G. R. K.; Van Der Sluys, L. S.; Kiss, G.; Hoff, C. D. Organometallics 1992, 12, 3390, and references therein.
53. 2 ligand appears at l.8 ppm (ref 11c).
54. The well-known destabilizing effect of two mutually trans soft ligands attached to a soft metal center has been named "antisymbiotic effect" (Pearson, R. G. Inorg. Chem. 1973, 12, 712). More recently the term "transphobia" has been coined for pairs of ligands (see ref 11g and: Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3067). For irons influence of common ligands see: Hartley, F. R. Chem. Soc. Rev. 1973, 2, 163.
55. The well-known destabilizing effect of two mutually trans soft ligands attached to a soft metal center has been named "antisymbiotic effect" (Pearson, R. G. Inorg. Chem. 1973, 12, 712). More recently the term "transphobia" has been coined for pairs of ligands (see ref 11g and: Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3067). For irons influence of common ligands see: Hartley, F. R. Chem. Soc. Rev. 1973, 2, 163.
56. The well-known destabilizing effect of two mutually trans soft ligands attached to a soft metal center has been named "antisymbiotic effect" (Pearson, R. G. Inorg. Chem. 1973, 12, 712). More recently the term "transphobia" has been coined for pairs of ligands (see ref 11g and: Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3067). For irons influence of common ligands see: Hartley, F. R. Chem. Soc. Rev. 1973, 2, 163.
57. Hiraki, K.; Fuchita, Y.; Takechi, K. Inorg. Chem. 1981, 20, 4316.
58. (a) Domenioano, A.; Vaciago, A.; Coulson, C. A. Acta Crystallogr., Sect. B 1975, 31, 221.
59. (b) Domenicano, A.; Mazzeo, P.; Vaciago, A. Tetrahedron Lett. 1976, 1029.
60. (c) Norrestam, R.; Schepper, L. Acta Chem. Scand., Ser. A 1981, 35, 91.
61. (d) Domenicano, A.; Murray-Rust, P.; Vaciago, A. Acta Crystallogr., Sect. B 1983, 39, 457.
62. (a) Braunstein, P.; Matt, D.; Dusausoy, Y.; Fischer, J.; Mitschler, A.; Ricard, L. J. Am. Chem. Soc. 1981, 103, 5115.
63. (b) Falvello, L. R.; Fernández, S.; Navarro, R.; Urriolabeitia, E. P. Inorg. Chem. 1996, 35, 3064.
64. For some structures of Pt(II) aquo complexes see: ionic: (a) Britten, J. P.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
65. (b) Rauter, H.; Hillgeris, E. C.; Erxleben, A.; Lippert, B. J. Am. Chem. Soc. 1994, 116, 616.
66. (c) Meinema, H. A.; Verbeek, F.; Marsman, J. W.; Bulten, E. J.; Dabrowiak, J. C.; Krishnan, B. S.; Spek, A. L. Inorg. Chim. Acta 1988, 114, 127.
67. (d) Rochon, F. D.; Melanson, R. Inorg. Chem. 1987, 26, 989
68. neutral: (e) Intini, F. P.; Lanfranchi, M.; Natile, G.; Pacifico, C.; Tiripicchio, A. Inorg. Chem. 1996, 35, 1715.
69. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
70. Dunitz, J. D.; Taylor, R. Chem. Eur. J. 1997, 3, 89.
71. (a) Bartolomé, C.; Espinet, P.; Martín-Álvarez, J. M.; Villafañe, F. Manuscript in preparation
72. (b) Romeo, R. Comments Inorg. Chem. 1990, 11, 21.
73. (b) Minniti, D. Inorg. Chem. 1994, 33, 2631.
74. (c) Casado, A. L.; Casares, J. A.; Espinet, P. Inorg. Chem. 1998, 37, 4154.
75. 3 solutions with different concentrations of water were titrated by NMR by integration of the water single versus ferrocene added as reference.
76. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
77. Cope, A. C.; Friedrich, E. C. J. Am. Chem. Soc. 1968, 90, 909.
78. Stephenson, T. A.; Morehouse, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. 1965, 3632.
79. Gutiérrez, M. A.; Newkome, G. R.; Selbin, J. J. Organomet. Chem. 1980, 202, 341.
80. Cope, A. C.; Siekman, R. W. J. Am. Chem. Soc. 1965, 87, 3272.
81. Buey, J.; Espinet, P. J. Organomet. Chem. 1996, 507, 137. Based on the method described in: Onoue, H.; Moritani, I. J. Organomet. Chem. 1972, 43, 431.
82. Buey, J.; Espinet, P. J. Organomet. Chem. 1996, 507, 137. Based on the method described in: Onoue, H.; Moritani, I. J. Organomet. Chem. 1972, 43, 431.
83. Thompson, J. M.; Heck, R. F. J. Org. Chem. 1975, 40, 2667.
84. (a) Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Org. Chem. 1987, 325, 13.
85. (b) Scholz, M.; Roesky, H. W.; Stalke, D.; Keller, K.; Edelmann, F. T. J. Organomet. Chem. 1989, 366, 73.
86. SMART diffractometer control software; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
87. SAINT integration software; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1994.
88. Sheldrick, G. M. SADABS: A program for absorption correction with the Siemens SMART system; University of Göttingen: Germany, 1996.
89. SHELXTL program system version 5.1; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
90. International Tables for Crystallography: Kluwer: Dordrecht, 1992; Vol. C.