A unique Au-Ag-Au triangular motif in a trimetallic halonium dication: Silver incorporation in a gold(I) catalyst

Chemistry - A European Journal

Volumn 19, Issue 37, 2013, Pages 12264-12271

  Zhu, Yuyang ^a   Day, Cynthia S ^a   Zhang, Lin ^a   Hauser, Katarina J ^a   Jones, Amanda C ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

aurophilicity; cluster compounds; gold; pi interactions; silver

Indexed keywords

AUROPHILIC INTERACTION; AUROPHILICITY; CLUSTER COMPOUNDS; DISPERSION CORRECTION; METALLOPHILIC INTERACTIONS; PI INTERACTIONS; SOLUTION CHEMISTRY; SOLUTION STRUCTURES;

ATOMS; CHELATION; CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; GOLD; MIXTURES; PHOSPHORUS COMPOUNDS;

SILVER;

EID: 84883460170     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302152     Document Type: Article

References (67)

1. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519
2. Angew. Chem. Int. Ed. 2007, 46, 3410-3449
3. A. Arcadi, Chem. Rev. 2008, 108, 3266-3325
4. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
5. D. J. Gorin, B. D. Sherry, F. Dean Toste, Chem. Rev. 2008, 108, 3351-3378.
6. H. Schmidbaur, A. Schier, Organometallics 2010, 29, 2-23.
7. D. Weber, M. R. Gagné, Org. Lett. 2009, 11, 4962-4965.
8. D. Wang, R. Cai, S. Sharma, J. Jirak, S. K. Thummanapelli, N. G. Akhmedov, H. Zhang, X. Liu, J. L. Petersen, X. Shi, J. Am. Chem. Soc. 2012, 134, 9012-9019.
9. H. Schmidbaur, A. Schier, Z. Naturforsch B. 2011, 66b, 329-350.
10. S. Gaillard, J. Bosson, R. S. Ramõn, P. Nun, A. M. Z. Slawin, S. P. Nolan, Chem. Eur. J. 2010, 16, 13729-13740.
11. Y. Zhu, C. S. Day, A. C. Jones, Organometallics 2012, 31, 7332-7335.
12. K. Zhang, J. Prabhavathy, J. H. K. Yip, L. L. Koh, G. K. Tan, J. J. Vittal, J. Am. Chem. Soc. 2003, 125, 8452-8453.
13. R. Uson, A. Laguna, M. V. Castrillo, Synth. React. Inorg. Met.-Org. Chem. 1979, 9, 317-324.
14. H. Schmidbaur, A. Hamel, N. W. Mitzel, A. Schier, S. Nogai, Proc. Natl. Acad. Sci. USA 2002, 99, 4916-4921
15. A. Hamel, N. W. Mitzel, H. Schmidbaur, J. Am. Chem. Soc. 2001, 123, 5106-5107
16. A. Bayler, A. Bauer, H. Schmidbaur, Chem. Ber. 1997, 130, 115-118.
17. S. G. Weber, F. Rominger, B. F. Straub, Eur. J. Inorg. Chem. 2012, 2863-2867.
18. A. Slade, H. Schmidbaur, Z. Naturforsch. B 1997, 52b, 301-303.
19. X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 5802-5803.
20. N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136
21. M. Preisenberger, A. Schier, H. Schmidbaur, J. Chem. Soc. Dalton Trans. 1999, 1645-1650
22. S. Komiya, J. K. Kochi, J. Organomet. Chem. 1977, 135, 65-72. In contrast, a gold triflate with a unique di(c-hexyl)phosphine ligand with a shielding arene substituent could be isolated
23. S. Doherty, J. G. Knight, A. S. K. Hashmi, C. H. Smyth, N. A. B. Ward, K. J. Robson, S. Tweedley, R. W. Harrington, W. Clegg, Organometallics 2010, 29, 4139-4147.
24. 2) contain 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
25. H. Schmidbaur, A. Schier, Chem. Soc. Rev. 2012, 41, 370-412
26. H. Schmidbaur, A. Schier, Chem. Soc. Rev. 2008, 37, 1931-1951.
27. E. Herrero-Gõmez, C. Nieto-Oberhuber, S. Lõpez, J. Benet-Buchholz, A. M. Echavarren, Angew. Chem. 2006, 118, 5581-5585
28. Angew. Chem. 2006, 118, 5581-5585
29. P. Pérez-Galán, N. Delpont, E. Herrero-Gõmez, F. Maseras, A. M. Echavarren, Chem. Eur. J. 2010, 16, 5324-5332.
30. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
31. S. V. Lindeman, R. Rathore, J. K. Kochi, Inorg. Chem. 2000, 39, 5707-5716.
32. N. Savjani, D.-A. Roşca, M. Schormann, M. Bochmann, Angew. Chem. 2013, 125, 908-911
33. Angew. Chem. Int. Ed. 2013, 52, 874-877.
34. A. V. Vasilyev, S. V. Lindeman, J. K. Kochi, Chem. Commun. 2001, 909-910.
35. K. Matsumoto, R. Hagiwara, Y. Ito, O. Tamada, J. Fluorine Chem. 2001, 110, 117-122.
36. H. G. Raubenheimer, H. Schmidbaur, Organometallics 2012, 31, 2507-2522.
37. T. J. Robilotto, J. Bacsa, T. G. Gray, J. P. Sadighi, Angew. Chem. 2012, 124, 12243-12246
38. Angew. Chem. Int. Ed. 2012, 51, 12077-12080.
39. F. Scherbaum, A. Grohmann, B. Huber, C. Krüger, H. Schmidbaur, Angew. Chem. 1988, 100, 1602-1604
40. Angew. Chem. Int. Ed. Engl. 1988, 27, 1544-1546.
41. A. N. Nesmeyanov, E. G. Perevalova, Y. T. Struchkov, M. Y. Antipin, K. I. Grandberg, V. P. Dyadhenko, J. Organomet. Chem. 1980, 201, 343-349.
42. G. A. Olah, G. Rasul, M. Hachoumy, A. Burrichter, G. K. S. Prakash, J. Am. Chem. Soc. 2000, 122, 2737-2741
43. G. A. Olah, D. A. Klumpp, in Superelectrophiles and Their Chemistry, Wiley, Hoboken, 2008, p. 120.
44. C. Topf, S. Leitner, U. Monkowius, Acta Crystallogr.Sect. E 2012, 68, m 272
45. X. Wang, S. Liu, L.-H. Weng, G.-X. Jin, Organometallics 2006, 25, 3565-3569.
46. M. C. Blanco, E. J. Fernández, M. E. Olmos, O. Crespo, A. Laguna, P. G. Jones, Organometallics 2002, 21, 2426-2429.
47. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
48. In computations on geminally diaurated gold(I) aryls, the PBE0 functional was used and the gold-gold distances were constrained in order to achieve a good fit:, E. Heckler, M. Zeller, A. D. Hunter, T. G. Gray, Angew. Chem. 2012, 124, 6026-6030
49. Angew. Chem. Int. Ed. 2012, 51, 5924-5928.
50. J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615-6620.
51. For use of the earlier generation ωB97X functional with gold clusters, see:, J. V. Koppen, M. Hapka, M. M. Szczȩśniak, G. Chałasiński, J. Chem. Phys. 2012, 137, 114302-114315.
52. H. Fang, X.-G. Zhang, S.-G. Wang, Phys. Chem. Chem. Phys. 2009, 11, 5796-5804.
53. I. Mayer, Chem. Phys. Lett. 1983, 97, 270-274
54. I. Mayer, Int. J. Quantum Chem. 1984, 26, 151-154
55. A. J. Bridgeman, G. Cavigliasso, L. R. Ireland, J. Rothery, J. Chem. Soc. Dalton Trans. 2001, 2095-2108.
56. A "non-negligible" MBO of 0.14 was also computed for an NHC dinuclear gold hydroxide and used as evidence of a gold-gold interaction:, R. S. Ramõn, S. Gaillard, A. Poater, L. Cavallo, A. M. Z. Slawin, S. P. Nolan, Chem. Eur. J. 2011, 17, 1238-1246.
57. The CDA was made using the Multiwfn Program version 2.6.1. For the introduction of Multiwfn 2.1.2 see:, T. Lu, F. Chen, J. Comput. Chem. 2012, 33, 580-592.
58. S. Dapprich, G. Frenking, J. Phys. Chem. 1995, 99, 9352-9362.
59. L. Gao, M. A. Peay, D. V. Partyka, J. B. Updegraff III, T. S. Teets, A. J. Esswein, M. Zeller, A. D. Hunter, T. G. Gray, Organometallics 2009, 28, 5669-5681.
60. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926
61. A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735-746.
62. K. B. Wiberg, Tetrahedron 1968, 24, 1083-1096.
63. A. S. K. Hashmi, M. C. Blanco, E. Kurpejovic̈, W. Frey, J. W. Bats, Adv. Synth. Catal. 2006, 348, 709-713.
64. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5653
65. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100
66. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
67. M. Dolg, U. Wedig, H. Stoll, H. Preuss, J. Chem. Phys. 1987, 86, 866-872.