Fine-tuning the electronic properties of highly stable organometallic CuIII complexes containing monoanionic macrocyclic ligands

Chemistry - A European Journal

Volumn 11, Issue 17, 2005, Pages 5146-5156

  Xifra, Raül ^a   Ribas, Xavi ^a   Llobet, Antoni ^b   Poater, Albert ^a   Duran, Miquel ^a   Sola, Miquel ^a   Stack, T D P ^c   Benet Buchholz, Jordi ^d   Donnadieu, Bruno ^e   Manía, José ^f   Parella, Teodor ^b  

^a UNIVERSITY OF GIRONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c STANFORD UNIVERSITY   (United States)

^d INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^e LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^f UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

C H activation; Copper(III) complexes; Density functional calculations; Electrochemistry; Spectroscopic properties

Indexed keywords

COMPLEXATION; COPPER COMPOUNDS; ELECTROCHEMISTRY; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; REDOX REACTIONS; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS; STRUCTURE (COMPOSITION); ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION ANALYSIS;

C-H ACTIVATION; COPPER(III) COMPLEXES; DENSITY FUNCTIONAL CALCULATIONS; SPECTROSCOPIC PROPERTIES;

ORGANOMETALLICS;

EID: 24344461366     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500088     Document Type: Article

References (73)

1. a) J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke in Principles and Applications of Organotransition Metal Chemistry, 2nd ed., University Science, Mill Valley, 1987, Chapter 7;
2. b) A. E. Martell, D. T. Sawyer, Oxygen Complexes and Oxygen Activation by Transition Metals, Texas A & M University, 1987;
3. c) M. D. Fryzuk, S. A. Johnson, Coord. Chem. Rev. 2000, 200-202, 379-409;
4. d) M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866-3898:
5. Angew. Chem. Int. Ed. 2001, 40, 3750-3781;
6. e) W. D. Jones, Acc. Chem. Res. 2003, 36, 140-146;
7. f) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759-1792.
8. a) J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507-514;
9. b) J. M. Thomas, R. Raja, G. Sankar, R. G. Bell, Acc. Chem. Res. 2001, 34, 191-200;
10. c)H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 257, 1995-1997;
11. d) R. H. Crabtree, Chem. Rev. 1995, 95, 987-1007;
12. e) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932.
13. M. J. Gradassi, N. W. Green, Fuel Process. Technol. 1995, 42, 65-83.
14. M. Gandelman, L. J. W. Shimon, D. Milstein, Chem. Eur. J. 2003, 9, 4295-4300.
15. X. Ribas, D. A. Jackson, B. Donnadieu, J. Mahía, T. Parella, R. Xifra, B. Hedman, K. O. Hodgson, A. Llobet, T. D. P. Stack, Angew. Chem. 2001, 113, 3117-3120;
16. Angew. Chem. Int. Ed. 2002, 41, 2991-2994.
17. L. L. Diaddario, W. R. Robinson, D. L. Margerum, Inorg. Chem. 1983, 22, 1021-1025.
18. I. H. Wasbotten, T. Wondimageng, A. Ghosh, J. Am. Chem. Soc. 2002, 124, 8104-8116.
19. a) H. Furuta, H. Maeda, A. Osuka, J. Am. Chem. Soc. 2000, 722, 803-807;
20. b) M. Stepien, L. Latos-Grazynski, Chem. Eur. J. 2001, 7, 5113-5117.
21. a) M. A. Willert-Porada, D. J. Burton, N. C. Baenziger, J. Chem. Soc., Chem. Commun. 1989, 1633-1634;
22. b) D. Naumann, T. Roy, K. F. Tebbe, W. Crump. Angew. Chem. 1993, 105, 1555-1556:
23. Angew. Chem. Int. Ed. Engl. 1993, 32, 1482-1483;
24. c) R. Eujen, B. Hoge, D. J. Brauer, J. Organomet. Chem. 1996, 59, 7-20.
25. a) T. D. P. Stack, Dalton Trans. 2003, 1881-1889;
26. b) N. W. Aboelella, E. A. Lewis, A. M. Reynolds, W. W. Brennessel, C. J. Cramer, W. B. Tolman, J. Am. Chem. Soc. 2002, 124, 10660-10661.
27. S. K. Burke, Y. Xu, D. W. Margerum, Inorg. Chem. 2003, 42, 5807-5817.
28. D. H. R. Barton, N. C. Delanghe, H. Patin, Tetrahedron 1997, 53, 16017-16028.
29. A. Bencini, M. I. Burguete, E. Garcia-España, S. V. Luis, J. F. Miravet, C. Soriano, J. Org. Chem. 1993, 58, 4749-4753.
30. C. Bazzicalupi, A. Bencini, A. Bianchi, V. Fusi, E. Garcia-España, P. Paoletti, P. Paoli, B. Valtancoli, Inorg. Chem. 1993, 32, 4900-4908.
31. a) K. Hiraki, J. Tsutsumida, Y. Fuchita, Chem. Lett. 1986, 337-340;
32. b) K. Hiraki, Y. Fuchita, Y. Ohta, J. Tsutsumida, K. I. Hardcastle, J. Chem. Soc., Dalton Trans. 1992, 833-836;
33. c) A. Chellini, G. B. Giovenzana, R. Pagliarin, G. Palmisano, M. Sisti, Helv. Chim. Acta 2000. 83, 793-800.
34. a) G. Golub, H. Cohen, P. Paoletti, A. Bencini, L. Messori, I. Bertini, D. Meyerstein, J. Am. Chem. Soc. 1995, 117, 8353-8361;
35. b) D. Meyerstein, Coord. Chem. Rev. 1999, 185-186, 141-147.
36. a) P. V. Bernhardt, J. Am. Chem. Soc. 1997, 119, 771-774;
37. b) P. V. Bernhardt, Inorg. Chem. 2001, 40, 1086-1092;
38. c) P. V. Bernhardt, P. Comba, T. W. Hambley, Inorg. Chem. 1993, 32, 2804-2809;
39. d) M. M. Bernardo, M. J. Heeg, R. R. Schroeder, L. A. Ochrymowycz, D. B. Rorabacher, Inorg. Chem. 1992, 31, 191-198.
40. It is important to bear in mind the existence of a certain controversy on the purity of the compounds reported in the work published by Meyerstein (see ref. [16a]) and Bernhardt (see ref. [17a]).
41. a) J. Hanss, H.-J. Krüger, Angew. Chem. 1996, 108, 2989-2991;
42. Angew. Chem. Int. Ed. Engl. 1996, 35, 2827-2830;
43. b) J. Hanss, A. Beckmann, H.-J. Krüger, Eur. J. Inorg. Chem. 1999, 163-172.
44. E. I. Solomon M. E. Hanson in Inorganic Electronic Structure and Spectroscopy, Vol. 2 (Eds.: E. I Solomon, A. B. P. Lever), Wiley, 1999, Chapter 1.
45. a) L. Bernasconi, J. Blumberger, M. Sprik, R. Vuilleumier, J. Chem. Phys. 2004, 121, 11885-11899;
46. b) X. Ribas, J. C. Dias, J. Morgado, K. Wurst, E. Molins, E. Ruiz, M. Almeida, J. Veciana, C. Rovira, Chem. Eur. J. 2004, 10, 1691-1704;
47. c) Y. Yamaguchi, S. Yokoyama, S. Mashiko, J. Chem. Phys. 2002, 116, 6541-6548;
48. d) Z.-L. Cai, K. Sendt, J. R. Reimers, J. Chem. Phys. 2002, 117, 5543-5549.
49. S. J. A. van Gisbergen, A. Rosa, G. Ricciardi, E. J. Baerends, J. Chem. Phys. 1999, 111, 2499-2506.
50. A. Altomare, G. Cascarano, G. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435-436.
51. SHELX-97 (includes SHELXS97. SHELXL97, CIFTAB), Programs for Crystal Structure Analysis (Release 97-2), G. M. Sheldrick, University of Göttingcn (Germany), 1998.
52. SHELXS-86. Programs for the Solution of Crystal Structures; G. M. Sheldrick, University of Göttingen (Germany), 1998.
53. SHELX-93, G. M. Sheldrick, University of Göttingen (Germany), 1998.
54. E. J. Baerends, D. E. Ellis, P. Ros, Chem. Phys. 1973, 2, 41-51.
55. C. Fonseca Guerra, O. Visser, J. G. Snijders, G. te Velde, E. J. Baerends, Methods and Techniques for Computational Chemistry, STEF, Cagliari, 1995, p. 305.
56. G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. Van Gisbergen, G. J. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-967.
57. W. Ravenek, Algorithms and Applications on Vector and Parallel Computers, Elsevier, Amsterdam, 1987.
58. G. te Velde, E. J. Baerends, J. Comp. Phys. 1992, 99, 84-98.
59. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
60. J. P. Perdew, Phys. Rev. B 1986, 33, 8822-8824.
61. a) E. K. U. Gross, J. F. Dobson, M. Petersilka, Density Functional Theory (Ed.: R. F. Nalewajski), Springer, Heidelberg, 1996;
62. b) S. J. A. van Gisbergen, J. G. Snijders, E. J. Baerends, Comput. Phys. Commun. 1999, 118, 119-138.
63. R. van Leeuwen, E. J. Baerends, Phys. Rev. A 1994, 49, 2421-2431.
64. ADF2002.03, E. J. Baerends, J. A. Autschbach, A. Bérces, C. Bo, P. M. Boerrigter, L. Cavallo, D. P. Chong, L. Deng, R. M. Dickson, D. E. Ellis, L. Fan, T. H. Fischer, C. Fonseca Guerra, S. J. A. van Gisbergen, J. A. Groeneveld, O. V. Gritsenko, M. Grüning, F. E. Harris, P. van den Hoek, H. Jacobsen, G. van Kessel, F. Kootstra, E. van - Lenthe, V. P. Osinga, S. Patchkovskii, P. H. T. Philipsen, D. Post, C. C. Pye, W. Ravenek, P. Ros, P. R. T. Schipper, G. Schreckenbach, J. G. Snijders, M. Solà, M. Swart, D. Swerhone, G. te Velde, P. Vernooijs, L. Versluis, O. Visser, E. van Wezenbeek, G. Wiesenekker, S. K. Wolff, T. K. Woo, T. Ziegler, Vrije Universiteit Amsterdam, Amsterdam, 2002.
65. G. J. Snijders, E. J. Baerends, P. Vernooijs, At. Nucl. Data Tables 1982, 26, 483-509.
66. P. Vernooijs, E. J. Baerends, Slater Type Basis Functions for the Whole Periodic System. Internal Report, Vrije Universiteit of Amsterdam, Amsterdam, 1981.
67. J. Krijn, E. J. Baerends, Fit Functions in the HFS Method. Internal Report (in Dutch), Vrije Universiteit of Amsterdam, Amsterdam, 1984.
68. E. van Lenthe, E. J. Baerends, J. Comput. Chem. 2003, 24, 1142-1156.
69. A. Klamt, G. Schüürmann, J. Chem. Soc., Perkin Trans. 2 1993, 799-805.
70. C. C. Pye, T. Ziegler, Theor. Chem. Acc., 1999, 101, 396-408.
71. Handbook of Chemistry and Physics, 83rd ed. (Ed.: D. R. Lide), CRC Press, Boca Raton FL, 2002-2003.
72. Gaussian 98 (Revision A. 11), 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, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, 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, 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, 2001.
73. MOLEKEL 4.0, P. Flükiger, H. P. Lüthi, S. Portmann, J. Weber, Swiss Center for Scientific Computing, Manno (Switzerland), 2000.