Trinuclear triangular copper(II) clusters - Synthesis, electrochemical studies and catalytic peroxidative oxidation of cycloalkanes

European Journal of Inorganic Chemistry

Volumn , Issue 5, 2009, Pages 666-676

  Di Nicola, Corrado ^a   Garau, Federica ^b,c   Karabach, Yauhen Y ^c   Martins, Luísa M D R S ^c,d   Monari, Magda ^e   Pandolfo, Luciano ^b   Pettinari, Claudio ^a   Pombeiro, Armando J L ^c  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

^c INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^d INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

^e UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Catalytic peroxidative oxidation; Cluster compounds; Copper; Copper(II) trinuclear complexes; Electrochemistry; Oxidation

Indexed keywords

CARBOXYLATION; CATALYTIC OXIDATION; COPPER COMPOUNDS; MAGNETIC SUSCEPTIBILITY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SUPRAMOLECULAR CHEMISTRY; ULTRAVIOLET VISIBLE SPECTROSCOPY;

CATALYTIC PEROXIDATIVE OXIDATION; CLUSTER COMPOUNDS; CLUSTER SYNTHESIS; COPPER(II) TRINUCLEAR COMPLEX; CYCLO-ALKANES; ELECTROCHEMICAL STUDIES; HEXANOATE; PEROXIDATIVE OXIDATION; TRINUCLEAR; TRINUCLEAR COMPLEX;

ELECTROCHEMISTRY;

EID: 60149095862     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200800842     Document Type: Article

References (91)

1. a) G. La Monica, G. A. Ardizzoia, Prog. Inorg. Chem. 1997, 46, 151-238;
2. b) D. E. Fenton, Advances in Inorganic and Bioinorganic Mechanisms (Ed.: A. G. Sykes), Academic Press, London, 1983, vol. 2;
3. c) S. Ménage, S. E. Vitols, P. Bergerat, E. Codjovi, O. Kahn, J.-J. Girerd, M. Guillot, X. Solans, T. Calvet, Inorg. Chem. 1991, 30, 2666-2671;
4. d) Magnetic Molecular Materials (Eds.: D. Gatteschi, O. Kahn, J. S. Miller, F. Palacio); NATO ASI Series 198; Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991;
5. e) D. E. Fenton, H. Okawa, J. Chem. Soc., Dalton Trans. 1993, 1349-1357;
6. f) M. Thomann, O. Kahn, J. Guilhem, F. Varret, Inorg. Chem. 1994, 33, 6029-6037;
7. g) E. I. Solomon, U. M. Sundaram, T. E. Machonkin, Chem. Rev. 1996, 96, 2563-2605;
8. h) W. Kaim, J. Rall, Angew. Chem. Int. Ed. Engl. 1996, 35, 43-60;
9. i) R. H. Holm, P. Kennepohl, E. I. Solomon, Chem. Rev. 1996, 96, 2239-2314;
10. j) A. P. Sadimenko, S. S. Basson, Coord. Chem. Rev. 1996, 147, 247-297;
11. k) O. Kahn, Chem. Phys. Lett. 1997, 265, 109;
12. l) O. Roubeau, J. M. A. Gómez, E. Balskus, J. J. A. Kolnar, J. G. Haasnoot, J. Reedijk, New J. Chem. 2001, 25, 144-150.
13. a) J. P. Klinman, Chem. Rev. 1996, 96, 2541-2562;
14. b) A. P. Cole, D. E. Root, P. Mukherjee, E. I. Solomon, T. D. P. Stack, Science 1996, 273, 1848-1850;
15. c) S. J. Elliot, M. Zhu, L. Tso, H.-H. T. Nguyen, J. H.-K. Yip, S. I. Chan, J. Am. Chem. Soc. 1997, 119, 9949-9955;
16. d) J. J. R. Fraústo da Silva, R. J. P. Williams, The Biological Chemistry of the Elements, Oxford University Press, Oxford, 2001;
17. e) S. Itoh in Comprehensive Coordination Chemistry, vol. 8 (Eds.: J. A. McCleverty, T. J. Meyer, L. Que, W. B. Tolman), 2nd ed., Elsevier, Dordrecht, 2003, chap. 8.15, pp. 369-393;
18. f) D. H. Lee in Comprehensive Coordination Chemistry, vol. 8 (Eds.: J. A. McCleverty, T. J. Meyer, L. Que, W. B. Tolman), 2nd ed., Elsevier, Dordrecht, 2003, chap. 8.17, pp. 437-457;
19. g) M. Ayala, E. Torres, Appl. Catal. A 2004, 272, 1-13;
20. h) R. L. Lieberman, A. C. Rosenzweig, Crit. Rev. Biochem. Mol. Biol. 2004, 39, 147-164;
21. i) R. L. Lieberman, A. C. Rosenzweig, Nature 2005, 434, 177-182;
22. j) J. Yoon, E. I. Solomon, Inorg. Chem. 2005, 44, 8076-8086.
23. R. Huber, Angew. Chem. Int. Ed. Engl. 1989, 28, 848-869.
24. a) A. M. Kirillov, M. N. Kopylovich, M. V. Kirillova, M. Haukka, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Angew. Chem. Int. Ed. 2005, 44, 4345-4349;
25. b) A. M. Kirillov, M. N. Kopylovich, M. V. Kirillova, Y. Y. Karabach, M. Haukka, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Adv. Synth. Catal. 2006, 348, 159-174.
26. a) M. Casarin, C. Corvaja, C. Di Nicola, D. Falcomer, L. Franco, M. Monari, L. Pandolfo, C. Pettinari, F. Piccinelli, P. Tagliatesta, Inorg. Chem. 2004, 43, 5865-5876;
27. b) M. Casarin, C. Corvaja, C. Di Nicola, D. Falcomer, L. Franco, M. Monari, L. Pandolfo, C. Pettinari, F. Piccinelli, Inorg. Chem. 2005, 44, 6265-6276;
28. c) C. Di Nicola, Y. Y. Karabach, A. M. Kirillov, M. Monari, L. Pandolfo, C. Pettinari, A. J. L. Pombeiro, Inorg. Chem. 2007, 46, 221-230.
29. 3)CCOOH}], whose synthesis, through a different procedure, as well as its SCXRD crystal structure has been recently reported, see J.-H. Zhou, Z. Liu, Y.-Z. Li, Y. Song, X.-T. Chen, X.-Z. You, J. Coord. Chem. 2006, 59, 147-153.
30. H-bonds concerning data and figures reported in the Supporting Information have been obtained by using the CIF files supplied as Supporting Information in refs. 5b (compounds 1 and 4) and 5a (compound 2). To these CIF files are also referred the atom labels used here.
31. 4] paddlewheel moiety is present but only 19 of them refer to polymeric unsubstituted copper(II) carboxylates.
32. [15] software. CCDC-697289 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
33. SMART & SAINT Software Reference Manuals, version 5.051 (Windows NT Version), Bruker Analytical X-ray Instruments Inc., Madison, WI, 1998.
34. G. M. Sheldrick, SADABS, program for empirical absorption correction, University of Göttingen, Germany, 1996.
35. A. Altomare, M. C. Burla, M. Cavalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
36. G. M. Sheldrick, SHELXTLplus (Windows NT Version) Structure Determination Package, Version 5.1, Bruker Analytical Xray Instruments Inc., Madison, WI, USA, 1998.
37. Mercury: Visualisation and Analysis of Crystal Structures:C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. van de Streek, , J. Appl. Crystallogr. 2006, 39, 453-457.
38. E. Keller, SCHAKAL A Computer Program for the Graphic Representation of Molecular and Crystallographic Models, Institute for Crystallography of the University of Freiburg, Freiburg (Germany), 1997.
39. G. B. Deacon, R. J. Phillips, Coord. Chem. Rev. 1980, 33, 227-250.
40. 1H NMR, IR, MS, UV/Vis, Chemical Laboratory Practice, Springer-Verlag, Berlin, Germany, 1989.
41. a) J. G. A. Luijten, G. J. M. Van der Kerk, Recl. Trav. Chem. Pays-Bas 1963, 82, 1181-1188;
42. b) J. G. Vos, W. L. Groeneveld, Inorg. Chim. Acta 1977, 24, 123-126;
43. c) H. Okkersen, W. L. Groeneveld, J. Reedijk, Recl. Trav. Chem. Pays-Bas 1973, 92, 945-953.
44. a) G. Mezei, M. Rivera-Carrillo, R. G. Raptus, Inorg. Chim. Acta 2004, 357, 3721-3732;
45. b) P. A. Angaridis, P. Baran, R. Boča, F. Cervantes-Lee, W. Haase, G. Mezei, R. G. Raptis, R. Werner, Inorg. Chem. 2002, 41, 2219-2228.
46. It is well known that in ESI MS conditions aggregation phenomena, leading to oligomeric species, may occur. See, as an example a) M. Fujita, F. Ibukuro, H. Hagihara, K. Ogura, Nature 1994, 367, 720-723;
47. b) R. Colton, A. D'Agostino, J. C. Traeger, Mass Spectrom. Rev. 1995, 14, 79-106;
48. c) C. E. C. A. Hop, R. Bakhtiar, J. Chem. Educ. 1996, 73, A162, A164-169;
49. d) L. S. Bonnington, R. K. Coll, E. J. Gray, J. I. Flett, W. Henderson, Inorg. Chim. Acta 1999, 299, 213-221;
50. e) A. Cingolani, Effendy, M. Pellei, C. Pettinari, C. Santini, B. W. Skelton, A. H. White, Inorg. Chem. 2002, 41, 6633-6645.
51. M. W. Senko, IsoPro Isotopic Abundance Simulator, v. 2.1, National High Magnetic Field Laboratory, Los Alamos National Laboratory, Los Alamos, NM, 1994.
52. M. Casarin, A. Cingolani, C. Di Nicola, D. Falcomer, M. Monari, L. Pandolfo, C. Pettinari, Cryst. Growth Des. 2007, 4, 676-685.
53. C. Di Nicola, F. Garau, M. Monari, L. Pandolfo, C. Pettinari, Proceedings of VIII Congresso Nazionale di Chimica Supramolecolare, Trieste (Italy), Sept. 19-22, 2007, P53.
54. a) M. V. Kirillova, A. M. Kirillov, P. M. Reis, J. A. L. Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Catal. 2007, 248, 130-136, and references cited therein;
55. b) M. V. Kirillova, M. L. Kuznetsov, P. M. Reis, J. A. L. Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Am. Chem. Soc. 2007, 129, 10531-10545;
56. c) M. V. Kirillova, M. L. Kuznetsov, J. A. L. Silva, M. F. C. Guedes da Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, Chem. Eur. J. 2008, 14, 1828-1842.
57. A. M. Kirillov, M. Haukka, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Eur. J. Inorg. Chem. 2005, 2071-2080.
58. Y. Y. Karabach, A. M. Kirillov, M. F. C. Guedes da Silva, M. N. Kopylovich, A. J. L. Pombeiro, Cryst. Growth Des. 2006, 6, 2200-2203.
59. a) T. F. S. Silva, E. C. B. Alegria, L. R. Martins, A. J. L. Pombeiro, Adv. Synth. Catal. 2008, 350, 706-716;
60. b) E. C. B. Alegria, M. V. Kirillova, L. R. Martins, A. J. L. Pombeiro, Appl. Catal. A: Gen. 2007, 317, 43-52;
61. c) M. V. Kirillova, A. M. Kirillov, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Eur. J. Inorg. Chem. 2008, 3423-3427.
62. a) G. S. Mishra, A. J. L. Pombeiro, J. Mol. Catal. A 2005, 239, 96-102;
63. b) G. S. Mishra, A. J. L. Pombeiro, Appl. Catal. A: Gen. 2006, 304, 185-194;
64. c) G. S. Mishra, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Mol. Catal. A 2007, 265, 59-69;
65. d) G. S. Mishra, E. C. B. Alegria, L. R. Martins, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Mol. Cat. A: Chem. in press.
66. P. M. Reis, J. A. L. Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, Chem. Commun. 2000, 1845-1846.
67. P. M. Reis, J. A. L. Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Mol. Catal. A 2004, 224, 189-195.
68. Y. Y. Karabach, A. M. Kirillov, M. Haukka, M. N. Kopylovich, A. J. L. Pombeiro, J. Inorg. Biochem. 2008, 102, 1190-1194.
69. M. N. Kopylovich, A. M. Kirillov, A. K. Baev, A. J. L. Pombeiro, J. Mol. Catal. A 2003, 206, 163-178.
70. a) D. S. Nesterov, V. N. Kokozay, V. V. Dyakonenko, O. V. Shishkin, J. Jezierska, A. Ozarowski, A. M. Kirillov, M. N. Kopylovich, A. J. L. Pombeiro, Chem. Commun. 2006, 4605-4607;
71. b) S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44, 8955-8957;
72. c) G. B. Shul'pin, J. Gradinaru, Y. N. Kozlov, Org. Biomol. Chem. 2003, 1, 3611-3617;
73. d) R. Raja, P. Ratnasamy, Catal. Lett. 1997, 48, 1-10.
74. a) G. B. Shul'pin, J. Mol. Catal. A 2002, 189, 39-66;
75. b) G. B. Shul'pin, C. R. Chim. 2003, 6, 163-178.
76. a) M. Costas, M. P. Mehn, M. P. Jensen, L. Que Jr., Chem. Rev. 2004, 104, 939-986;
77. b) M. Costas, K. Chen, L. Que Jr., Coord. Chem. Rev. 2000, 200-20, 517-544;
78. c) G. Roelfes, M. Lubben, R. Hage, L. Que Jr., B. L. Feringa, Chem. Eur. J. 2000, 6, 2152-2159.
79. T. Hogan, A. Sen, J. Am. Chem. Soc. 1997, 119, 2642-2646.
80. nd edn., vol. 2, Wiley-VCH, New York, 2004, p. 215;
81. b) G. B. Shul'pin, Organic Reactions Catalyzed by Metal Complexes, Nauka, Moscow, 1988.
82. a) G. V. Nizova, B. Krebs, G. Süss-Fink, S. Schindler, L. Westerheide, L. G. Cuervo, G. B. Shul'pin, Tetrahedron 2002, 58, 9231-9237;
83. b) G. B. Shul'pin, Y. N. Kozlov, G. V. Nizova, G. Süss-Fink, S. Stanislas, A. Kitaygorodskiy, V. S. Kulikova, J. Chem. Soc., Perkin Trans. 2 2001, 2, 1351-1371;
84. c) G. Süss-Fink, L. Gonzalez, G. B. Shul'pin, Appl. Catal. A: Gen. 2001, 217, 111-117;
85. d) G. B. Shul'pin, G. Süss-Fink, J. Chem. Soc., Perkin Trans. 2 1995, 2, 1459-1463;
86. e) M. Kodera, H. Shimakoshi, K. Kano, Chem. Commun. 1996, 1737-1738;
87. f) H.-J. Schneider, W. Müller, J. Org. Chem. 1985, 50, 4609-4615;
88. g) G. B. Shul'pin, H. Stoeckli-Evans, D. Mandelli, Y. N. Kozlov, A. T. Vallina, C. B. Woitiski, R. S. Jimenez, W. A. Carvalho, J. Mol. Catal. A 2004, 219, 255-264.
89. P. M. Reis, J. A. L. Silva, A. F. Palavra, J. J. R. Fraústo da Silva, T. Kitamura, Y. Fujiwara, A. J. L. Pombeiro, Angew. Chem. Int. Ed. 2003, 42, 821-823.
90. R. L. Martin, H. Waterman, J. Chem. Soc. 1957, 2545-2551.
91. A. J. L. Pombeiro, M. F. C. Guedes da Silva, M. A. N. D. A. Lemos, Coord. Chem. Rev. 2001, 219-221, 53-80.