Structural, 103Rh NMR and DFT Studies of a Bis(phosphane)Rh III-Porphyrin Derivative

European Journal of Inorganic Chemistry

Volumn , Issue 17, 2009, Pages 2512-2523

  Munro, Orde Q ^a   Camp, Greville L ^a   Carlton, Laurence ^b  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

^b UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

103Rh NMR spectroscopy; Density functional calculations; GIAO; Phosphanes; Porphyrin

Indexed keywords

ATOMS; BOND LENGTH; CARBON; CHEMICAL DETECTION; CHEMICAL SHIFT; CONFORMATIONS; DENSITY FUNCTIONAL THEORY; DICHLOROMETHANE; PLATINUM COMPOUNDS; PORPHYRINS; RHODIUM COMPOUNDS; RUTHENIUM COMPOUNDS;

103RH NMR SPECTROSCOPY; DENSITY-FUNCTIONAL CALCULATIONS; DFT STUDY; DIANIONS; GIAO; NMR STUDIES; NMR-SPECTROSCOPY; PHOSPHANES; PORPHYRIN DERIVATIVES; SYNTHESIS AND CHARACTERIZATIONS;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 66549124592     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200800837     Document Type: Article

References (79)

1. Abbreviations: DFT = density functional theory, esd = estimated standard deviation, GIAO = gauge-independent atomic orbitais; TF5PP = dianion of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin, TPP = dianion of 5,10,15,20-tetraphenylporphyrin, OEP = 2,3,7,8,12,13,17,18- octaeťhylporphyrin dianion, 1-MepipZ = 1-methylpiperazine, THF = tetrahydroiuran; nd = not determined.
2. S. Ariel, D. Dolphin, G. Domazetis, B. R. James, T. W. Leung, S. J. Rettig, J. Trotter, G. M. Williams, Can. J. Chem. 1984, 62, 755-762.
3. B. R. James, D. Dolphin, T. W. Leung, F. W. B. Einstein, A. C. Willis, Can. J. Chem. 1984, 62, 1238-1245.
4. C-M. Che, J.-L. Zhang, R. Zhang, J.-S. Huang, T-S. Lai, WM. Tsui, X.-G. Zhou, Z.-Y. Zhou, N. Zhu, C. K. Chang, Chem. Eur. J. 2005, 11, 7040-7053.
5. E. Stulz, M. Maue, N. Feeder, S. J. Teat, Y.-F. Ng, A. D. Bond, S. L. Darling, J. K. M. Sanders, Inorg. Chem. 2002, 41, 52555268.
6. R. M. Belani, B. R. James, D. Dolphin, S. J. Rettig, Can. J. Chem. 1988, 66, 2072-2078.
7. L. Toupet, N. Legrand, A. Bondon, G. Simonneaux, Acta Crystallogr., Sect. C 1994, 50, 1014-1016.
8. M.-A. Pilard, M. Guillemot, L. Toupet, J. Jordanov, G. Simonneaux, Inorg. Chem. 1997, 36, 6307-6314.
9. L. Toupet, P. Soda.no, G. Simonneaux, Acta Crystallogr., Sect. C 1990, 46, 1631-1633.
10. a) C-M. Che, T-F. Lai, W-C Chung, WP. Schaefer, H. B. Gray, Inorg. Chem. 1987, 26, 3907-3911.
11. b) J. Xie, J.-S. Huang, N. Zhu, Z.-Y. Zhou, C-M. Che, Chem. Eur. J. 2005, 11, 24052416.
12. a) K. M. Kadish, J.-L. Cornillon, P. Mitaine, Y. J. Deng, J. D. Korp, Inorg. Chem. 1989, 28, 2534-2542
13. b) K. M. Kadish, Y J. Deng, J. D. Korp, Inorg. Chem. 1990, 29, 1036-1042.
14. Cambridge Structural Database (CSD), version 5.29 (July 2008); F. H. Allen, Acta Crystallogr., Sect. B 2002, 58, 380388.
15. a.) E. Stulz, S. M. Scott, Y.-F. Ng, A. D. Bond, S. J. Teat, S. L. Darling, N. Feeder, J. K. M. Sanders, Inorg. Chem. 2003, 42, 6564-6574
16. b) K. Fukushima, K. Funatsu, A. Ichimura, Y. Sasaki, M.. Suzuki, T. Fujihara, K. Tsuge, T. Imamura, Inorg. Chem. 2003, 42, 3187 - 3193
17. c) E. Stulz, S. M. Scott, A.D. Bond, S. J. Teat, J. K. M, Sanders, Chem. Eur. J. 2003, 9, 6039 - 6048.
18. B. B. Wayland, B. A. Woods, V.M. Minda, J. Chem. Soc., Chem. Commun. 1982, 634 - 635.
19. X. Li, R. Irie, S. Shinoda, Y. Saito, Nippon Kagaku Kaishi 1984, '271 - 276.
20. a) H. J. Callot, C. Piechocki, Tetrahedron Lett. 1980, 21, 3489 3492
21. b) H. J. Callot, F. Metz, C. Piechocki, Tetrahedron 1982, 38, 2365 - 2369
22. c) H. J. Callot, F. Metz, Nouv. J. Chim. 1985, 9, 167 - 171.
23. a) K. M. Kadish, Y. Hu, T. Boschi, P. Tagliatesta, Inorg. Chem. 1993, 32, 2996-3002
24. b) R. Guilard, K. M. Kadish, Chem. Rev. 1988, 88, 1121-1146.
25. III complexes in general include the following works
26. a) M. Soleilhavoup, L. Viau, G. Commenges, C. Lepetit, R. Chauvin, Eur. J. Inorg. Chem. 2003, 2, 207-212
27. b) M. Herberhold, H. Yan, W Milius, B. Wrackmeyer, Chem. Eur. J. 2002, 8, 388-395
28. c) S. Haep, M. Nieger, D. Gudat, M. Betke-Hornfeck, D. Schramm, Organometallics 2001, 20, 2679-2685.
29. R. G. Kidd, R. J. Goodfellow, in NMR and the Periodic Table (Eds.: R. K. Harris, B. E. Mann), Academic Press, New York, 1978, pp. 195 - 278.
30. J. R. Houston, M. M. Olmstead, W. H. Casey, Inorg. Chem. 2006, 45, 7799 - 7805.
31. D. J. Law, G. Bigam, R. G. Cavell, Can. J. Chem. 1995, 73, 635642.
32. a) B. R. Bender, M. Koller, D. Nanz, W. von Philipsborn, J Am. Chem. Soc. 1993, 115, 5889 - 890
33. b) L. Carlton, Magn. Reson. Chem. 1997, 35, 153-158
34. c) W. von Philipsborn, Chem. Soc. Rev. 1999, 28, 95-105
35. d) M. Herberhold, H. Yan, W. Milius, B. Wrackmeyer, Chem. Eur. J. 2002, 8, 388-395.
36. T. Boschi, S. Licoccia, P. Tagliatesta, Inorg. Chim. Acta 1987, 126, .157-160.
37. W. R. Scheidt, Y. J. Lee, Struct. Bonding (Berlin) 1987, 64, 170.
38. B. A. Kelly, A. J. Welch, P. Woodward, J. Chem. Soc., Dalton Trans. 1977, 2237-2242.
39. E. Stulz, S. M. Scott, A. D. Bond, S. Otto, J. K. M. Sanders, Inorg. Chem. 2003, 42, 3086-3096.
40. D. C Thackray, S. Ariel, T. W. Leung, K. Menon, B. R. James, J. Trotter, Can. J. Chem. 1986, 64, 2440-2446.
41. C. A. Tolman, Chem. Rev. 1977, 77, 313-348.
42. The relevant nonbonded contacts include C4a",C52 (3.197 Å), N2-C52 (3.275 Å), Cla-C66 (3.334 Å), and N1-C61 (3.298 Å) for the uppermost axial ligand in Figure 1.
43. O. Q. Munro, S. C. Shabalala, N. J. Brown, Inorg. Chem. 2001, 40, 3303-3317.
44. A. J. Parusel, S. Grimme, J. Porphyrins Phthalocyanines 2001, 5, 1-8.
45. L.-K. Choi, Y. Liu, Z. Wei, M. D. Ryan, Inorg. Chem. 1997, 36, 3113-3118.
46. A. Bax, R. H. Griffey, B. L. Hawkins, J. Am. Chem. Soc. 1983, 105, 7188-7190.
47. W. von Philipsborn, Chem. Soc. Rev. 1999,28, 95-105.
48. H. C. E. McFarlane, W. McFarlane, R. J. Wood, Bull, Soc. CMm. BeIg. 1976, 85, 864-871.
49. L. Öhrström, Comments Inorg. Chem. 1996, 18, 305-323.
50. T. H. Brown, P. J. Green, J. Am. Chem. Soc. 1970, 92, 23592362.
51. 13C NMR of Transition Metal Phosphine Complexes" in NMR 16, Basic Principles and Progress (Eds.: P. Diehl, E. Fluck, R. Kosfeld), Springer-Verlag, Berlin, 1979, pp. 47-49.
52. C. J. Jameson, D. Rehder, M. Hoch, J. Am. Chem. Soc 1987, 109, 2589-2594.
53. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
54. R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724-728.
55. N. Godbout, D. R. Salahub, J. Andzelm, E. Wimmer, Can. J. Chem. 1992, 70, 560-571.
56. K. Ruud, T. Helgaker, K. L. Bak, P. Jorgensen, H. J. A. Jensen, J. Chem.'Phys. 1993, 99, 3847-3859.
57. a) O. Q. Munro, H. M. Marques, P. G. Debrunner, K. Mohanrao, W. R. Scheidt, J. Am. Chem. Soc 1995, 117, 935-954
58. b)O. Q. Munro, P. S. Madlala, R. A. F. Warby, T. S. Seda, G. Hearne, Inorg. Chem. 1.999, 38, 4724-4736.
59. J. E. Carpenter, F. Weinhold, THEOCHEM 1.988, 169, 41-62.
60. F. A. Walker, in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, vol. 5, pp. 81-183.
61. O. Q. Munro, J. C. Bradley, R. D. Hancock, H. M. Marques, F. Marsicano, P. W Wade, J. Am. Chem. Soc. 1992, 114, 72187230.
62. O. Q. Munro, J. A. Serth-Guzzo, I. Turowska-Tyrk, K. Mohanrao, T. K. Shokhireva, F. A. Walker, P. G. Debrunner, W. R. Scheldt, J. Am. Chem. Soc. 1999, 121, 11144-11155.
63. C. Sosa, J. Andzelm, B. C. Elkin, E. Wimmer, K. D. Dobbs, D. A. Dixon, J. Phys. Chem. 1992, 96, 6630-6636.
64. M. Bühl, M. Hâkansson, A. H. Malimoudkhani, L. Öhrstrom, Organometallics 2000, 19, 5589 - 5596.
65. M. Bühl, Chem. Phys. Lett. 1997, 267, 251 - 257.
66. X. Xu, L. Fang, Z.-X. Chen, G.-C. Yang, S.-L. Sun, Z.-M. Su, J. Organomet. Chem. 2006, 691, 1927 - 1933.
67. Y. Ruiz-Morales, T. Ziegler, J. Phys. Chem. A 1998, 102, 3970 3976.
68. K. Eichele, R. E. Wasylishen, J. F. Corrigan, N. J. Taylor, A. J. Carty, K. W. Feindel, G. M. Bernard, J. Am. Chem. Soc. 2002, 124, 1541 - 1552.
69. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43-54.
70. G. H. Barnett, M. F. Hudson, K. M. Smith, J. Chem. Soc Perkin Trans. 1 1975, 1401-1403.
71. A. D. Adler, F. R. Longo, F. Kampas, J. Kim, J. Inorg. Nucl. Chem. 1970, 32, 2443-2445.
72. K. Harms, S. Wocadlo, XCAD4 - Program for Processing CAD4 Diffractometer Data, University of Marburg, Germany, 1995.
73. G. M. Sheldrick, SHELXS-97 and SHELXL-97 - Programs for Crystal Structure Solution and Refinement, release 97-2, University of Göttingen, Germany, 1997.
74. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.
75. A. Bax, R. H. Griffey, B. L. Hawkins, J. Magn. Reson. 1983, 55, 301-315.
76. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmanin, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C Strain, O. Parkas, 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. Cliallacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 03, revision D.01, Gaussian, Inc., Pittsburgh PA, 2004.
77. Gaus View 3.09, Graphical Interface to Gaussian 03, Gaussian Inc., Carnegie Office Park, Building 6, Pittsburgh PA 15106, USA, http://www.gaussian.com
78. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565-565.
79. The root mean square fit employed the Rh atom, axial P atoms and 24 porphyrin core atoms from each structure.