Phosphine and phosphonite complexes of a ruthenium(II) porphyrin. 1. Synthesis, structure, and solution state studies

Inorganic Chemistry

Volumn 41, Issue 20, 2002, Pages 5255-5268

  Stulz, Eugen ^a   Maue, Michael ^a   Feeder, Neil ^a   Teat, Simon J ^a   Ng, Yiu Fai ^a   Bond, Andrew D ^a   Darling, Scott L ^a   Sanders, Jeremy K M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5,15 BIS(3',5' DI TERT BUTYL)PHENYL 2,8,12,18 TETRAETHYL 3,7,13,17 TETRAMETHYLPORPHYRIN; BIS(DIPHENYLPHOSPHINO)ACETYLENE; DIETHYL(PHENYLACETENYL)PHOSPHONITE; DIPHENYL(PHENYLACETENYL)PHOSPHINE; LIGAND; METALLOPORPHYRIN; PHOSPHINE DERIVATIVE; PHOSPHONITE DERIVATIVE; PHOSPHORUS; PORPHYRIN; RUTHENIUM; TRIS(PHENYLACETENYL)PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTALLIZATION; CRYSTALLOGRAPHY; GEOMETRY; INFRARED SPECTROSCOPY; KINETICS; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SOLID STATE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0037037495     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic025727y     Document Type: Article

References (92)

1. (a) Yamaguchi, H.; Kamachi, M.; Harada, A. Angew. Chem., Int. Ed. 2000, 39, 3829.
2. (b) Norsten, T. B.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 1784.
3. (c) Imahori, H.; Arimura, M.; Hanada, T.; Nishimura, Y.; Yamazaki, I.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 335.
4. (d) Cho, H. S.; Jeong, D. H.; Yoon, M. C.; Kim, Y. H.; Kim, Y. R.; Kim, D.; Jeoung, S. C.; Kim, S. K.; Aratani, N.; Shinmori, H.; Osuka, A. J. Phys. Chem. A 2001, 705, 4200.
5. (e) Shediac, R.; Gray, M. H. B.; Uyeda, H. T.; Johnson, R. C.; Hupp, J. T.; Angiolillo, P. J.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 7017.
6. Mak, C. C.; Bampos, N.; Darling, S. L.; Montalti, M.; Prodi, L.; Sanders, J. K. M. J. Org. Chem. 2001, 66, 4476.
7. (a) Gryko, D. T.; Clausen, C.; Roth, K. M.; Dontha, N.; Bocian, D. F.; Kuhr, W. G.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7345.
8. (b) Li, J. Z.; Gryko, D.; Dabke, R. B.; Diers, J. R.; Bocian, D. F.; Kuhr, W. G.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7379.
9. (c) Collman, J. P.; Kendall, J. L.; Chen, J. L.; Collins, K. A.; Marchon, J. C. Inorg. Chem. 2000, 39, 1661.
10. (a) Haycock, R. A.; Hunter, C. A.; James, D. A.; Michelsen, U.; Sutton, L. R. Org. Lett. 2000, 2, 2435.
11. (b) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40.
12. (c) Imahori, H.; Norieda, H.; Yamada, H.; Nishimura, Y.; Yamazaki, I.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 100.
13. (d) Sun, L.; Hammarstrom, L.; Akermark, B.; Styring, S. Chem. Soc. Rev. 2001, 30, 36.
14. Kim, H. J.; Bampos, N.; Sanders, J. K. M. J. Am. Chem. Soc. 1999. 121, 8120.
15. Redman, J. E.; Feeder. N.; Teat, S. J.; Sanders, J. K. M. Inorg. Chem. 2001, 40, 2486.
16. Darling, S. L.; Stulz, E.; Feeder, N.; Bampos, N.; Sanders, J. K. M. New J. Chem. 2000, 24, 261.
17. Stulz, E.; Ng, Y.-F.; Scott, S. M.; Sanders, J. K. M. Chem. Commun. 2002, 524.
18. (a) Simonneaux, G.; Sodano, P. Inorg. Chem. 1988, 27, 3956.
19. (b) Simonneaux, G.; Sodano, P. J. Organomet. Chem. 1988, 349, C11.
20. (c) Guillemot, M.; Simonneaux, G. J. Chem. Soc., Chem. Commun. 1995, 2093.
21. Pilard, M. A.; Guillemot, M.; Toupet, L.; Jordanov, J.; Simonneaux, G. Inorg. Chem. 1997, 36, 6307.
22. Sodano, P.; Simonneaux, G.; Toupet, L. J. Chem. Soc., Dalton Trans. 1988, 2615.
23. (a) Rieger, P. H. Coord. Chem. Rev. 1994, 135, 203.
24. (b) Ohya, T.; Morohoshi, H.; Sato, M. J. Pharmacobio-Dyn. 1985, 8, S14.
25. Ohya, T.; Morohoshi, H.; Sato, M. Inorg. Chem. 1984, 23, 1303.
26. Wayland, B. B.; Sherry, A. E.; Bunn, A. G. J. Am. Chem. Soc. 1993, 115, 7675.
27. Ariel, S.; Dolphin, D.; Domazetis, G.; James, B. R.; Leung, T. W.; Rettig, S. J.; Trotter, J.; Williams, G. M. Can. J. Chem. 1984, 62, 755.
28. Chow, B. C.; Cohen, I. A. Bioinorg. Chem. 1971, 1, 57.
29. James, B. R.; Dolphin, D.; Leung, T. W.; Einstein, F. W. B.; Willis, A. C. Can. J. Chem. 1984, 62, 1238.
30. Cheng, R. J.; Lin, S. H.; Mo, H. M. Organometallics 1997, 16, 2121.
31. (a) Grass, V.; Lexa, D.; Momenteau, M.; Saveant, J. M. J. Am. Chem. Soc. 1997, 119, 3536.
32. (b) Collman, J.P.; Boulatov, R. J. Am. Chem. Soc. 2000, 122, 11812.
33. (a) Tsutsui, M.; Osterfeld, D.; Hoffman, L. M. J. Am. Chem. Soc. 1971, 93, 1820.
34. (b) Tsutsui, M.; Osterfeld, D.; Francis, J. N.; Hoffman, L. M. J. Coord. Chem. 1971, 115.
35. (c) Barley, M.; Becker, J. Y.; Domazetis, G.; Dolphin, D.; James, B. R. Can. J. Chem. 1983, 61, 2389.
36. Kadish, K. M.; Hu, Y.; Tagliatesta, P.; Boschi, T. J. Chem. Soc., Dalton Trans. 1993, 1167.
37. Tolman, C. A. Chem. Rev. 1977, 77. 313.
38. Müller, T. E.; Mingos, D. M. P. Transition Met. Chem. 1995, 20, 533.
39. Fernandez, A. L.; Reyes, C.; Prock, A.; Giering, W. P. J. Chem. Soc., Perkin Trans. 2 2000, 5, 1033.
40. Mathew, N.; Jagirdar, B. R. Organometallics 2000, 19, 4506.
41. (a) Taft, R. W. Steric Effects in Organic Chemistry; John Wiley & Sons: New York, 1956.
42. (b) Taft, R. W. J. Am. Chem. Soc. 1952, 74, 3120.
43. Hengefeld, A.; Kopf, J.; Rehder, D. Organometallics 1983, 2, 114.
44. Carty, A. J.; Hota, N. K.; Ng, T. W.; Patel, H. A.; O'Connor, T. J. Can. J. Chem. 1971, 49, 2706.
45. Twyman, L. J.; Sanders, J. K. M. Tetrahedron Lett. 1999, 40, 6681.
46. Carty, A. J.; Hota, N. K.; Ng, T. W.; Patel, H. A.; O'Connor, T. J. Can. J. Chem. 1971, 49, 2706.
47. Bharathi, P.; Periasamy, M. Organometallics 2000, 19, 5511.
48. Lang, H.; Zsolnai, L. J. Organomet. Chem. 1989, 369, 131.
49. Sheldrick, G. M. SHELXS-97; University of Göttingen: Göttingen, Germany, 1997.
50. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
51. Gil, J. M.; Sung, J. W.; Park, C. P.; Oh. D. Y. Synth. Commun. 1997, 27, 3171.
52. Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
53. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy, 2nd ed.; Oxford University Press: Oxford, 1993.
54. James, S. L.; Lozano, E.; Nieuwenhuyzen, M. Chem. Commun. 2000, 617.
55. Clark, H. C.; Ferguson, G.; Kapoor, P. N.; Parvez, M. Inorg. Chem. 1985, 24, 3924.
56. (a) Lee, H. M.; Bianchini, C.; Jia, G. C.; Barbaro, P. Organometallics 1999, 18, 1961.
57. (b) Ihmels, K.; Rehder, D. Organometallics 1985, 4, 1334.
58. Romeo, R.; Alibrandi, G. Inorg. Chem. 1997, 36, 4822.
59. (a) Webb, S. J.; Sanders, J. K. M. Inorg. Chem. 2000, 39, 5920.
60. (b) Webb, S. J.; Sanders, J. K. M. Inorg. Chem. 2000, 39, 5912.
61. Cheng, P. C.; Liu, I. C.; Hong, T. N.; Chen, J. H.; Wang, S. S.; Wang, S. L.; Lin, J. C. Polyhedron 1996, 15, 2733.
62. Abraham, R. J.; Marsden, I. Tetrahedron 1992, 48, 7489.
63. (a) Semmelmann, M.; Fenske, D.; Corrigan, J. F. J. Chem. Soc., Dalton Trans. 1998, 2541.
64. (b) Amoroso, A. J.; Johnson, B. F. G.; Lewis, J.; Massey, A. D.; Raithby, P. R.; Wong, W. T. J. Organomet. Chem. 1992, 440, 219.
65. (a) Smith, J. M.; Coville, N. J.; Cook, L. M.; Boeyens, J. C. A. Organometallics 2000, 19, 5273.
66. (b) White, D.; Taverner, B. C.; Coville, N. J.; Wade, P. W. J. Organomet. Chem. 1995, 495, 41.
67. (c) Smith, J. M.; Taverner, B. C.; Coville, N. J. J. Organomet. Chem. 1997, 530, 131.
68. Smith, J. M.; Coville, N. J. Organometallics 2001, 20, 1210.
69. Martin, A.; Orpen, A. G. J. Am. Chem. Soc. 1996, 118, 1464.
70. (a) Bubel, R. J.; Douglass, W.; White, D. P. J. Comput. Chem. 2000, 21, 239.
71. (b) Fernandez, A.; Reyes, C.; Prock, A.; Giering, W. P. Organometallics 1998, 17, 2503.
72. (c) Fernandez, A. L.; Lee, T. Y.; Reyes, C.; Prock, A.; Giering, W. P.; Haar, C. M.; Nolan, S. P. J. Chem. Soc., Perkin Trans. 2 1999, 2631.
73. (d) Woska, D.; Prock, A.; Giering, W. P. Organometallics 2000, 19, 4629.
74. (e) Joerg, S.; Drago, R. S.; Sales, J. Organometallics 1998, 17, 589.
75. Joerg, S.; Webster, C. E.; Drago, R. S.; Sales, J. Polyhedron 1999, 18, 1097.
76. Bosque, R.; Sales, J. J. Chem. Inf. Comput. Sci. 2001, 41, 225.
77. Hui, B. K. M.; Wong, W. T. J. Chem. Soc., Dalton Trans. 1998, 447.
78. Layer, T. M.; Lewis, J.; Martin, A.; Raithby, P. R.; Wong, W. T. J. Chem. Soc., Dalton Trans. 1992, 3411.
79. (a) Henderson, W. A.; Streuli, C. A. J. Am. Chem. Soc. 1960, 82, 5791.
80. (b) Allman, T.; Goel, R. G. Can. J. Chem. 1982, 60, 716.
81. Abdur-Rashid, K.; Fong, T. P.; Greaves, B.; Gusev, D. G.; Hinman, J. G.; Landau, S. E.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2000, 122, 9155.
82. Guillemin, J. C.; Savignac, P.; Denis, J. M. Inorg. Chem. 1991, 30, 2170.
83. Vogel, K. M.; Kozlowski, P. M.; Zgierski, M. Z.; Spiro, T. G. Inorg. Chim. Acta 2000, 297, 11.
84. (a) Buchler, J. W.; Kokisch, W.; Smith, P. D. Struct. Bonding 1978, 34, 79.
85. (b) Gross, Z.; Mahammed, A.; Barzilay, C. M. Chem. Commun. 1998, 1105.
86. Xu, D. F.; Murfee, H. J.; van der Veer, W. E.; Hong, B. J. Organomet. Chem. 2000, 596, 53.
87. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
88. Darling, S.; Feeder, N.; Sanders, J. K. M. 1999, private communication to the CCDC.
89. Stulz, E.; Sanders, J. K. M.; Montalti, M.; Prodi, L.; Zaccheroni, N.; Fabrizi de Biani, F.; Grigiotti, E.; Zanello, P. Inorg. Chem. 2002, 41, 5269.
90. 60
91. 31P): -180 ppm (free ligand), -121 ppm (mono-phosphine complex).
92. 31P nucleus, but theoretically the chemical shift differences upon complexation cannot be assigned purely to electronic effects upon formation of the Ru-P bond, because the influence of the ring current of the aromatic porphyrin system also has to be taken into account. The binding site of a ligand to a metalloporphyrin is located in the strongly shielding region of the π-system of the porphyrin, leading to a significant upfield shift of the resonance of the respective nuclei. As judged from proton NMR spectroscopy, however, the solution state geometries of the complexes are almost identical in all cases. The relative positions of the phosphorus atoms vary by 0.06 Å along the Ru-P axis orthogonal to the porphyrin plane. We assume the influence of the bond length differences to be negligible, and the observed chemical shift differences to arise from the electronic effects of the different bond types and a constant upfield shift caused by the ring current of the aromatic ring system. This problem has not been addressed as such in previous studies.