Synthesis and redox behaviour of the chalcogenocarbonyl dianions [(E)C(PPh2S)2]2?: Formation and structures of chalcogenchalcogen bonded dimers and a novel selone

Chemistry - A European Journal

Volumn 16, Issue 43, 2010, Pages 12977-12987

  Konu, Jari ^a   Chivers, Tristram ^a   Tuononen, Heikki M ^b  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

chalcogens; electronic structure; oxidation; radicals; tridentate ligands

Indexed keywords

DIMERS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; IODINE; LIGANDS; OXIDATION; SELENIUM; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

ANALOGOUS REACTIONS; CHALCOGENS; DFT CALCULATION; DIAMAGNETIC COMPLEX; DIANIONIC LIGANDS; DIANIONS; EPR SPECTROSCOPY; LITHIUM SALTS; ONE-ELECTRON OXIDATION; PARAMAGNETIC SPECIES; RADICAL ANIONS; RADICALS; SOLID-STATE STRUCTURES; STRUCTURAL FEATURE; TETRAMETHYLETHYLENEDIAMINE; TRANSIENT RADICALS; TRIDENTATE LIGANDS; TWO-ELECTRON OXIDATION;

LITHIUM;

EID: 78449292348     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001699     Document Type: Article

References (83)

1. For reviews, see
2. I. Haiduc, in Comprehensive Coordination Chemistry II (Eds.:, J.A. McCleverty, T.J. Meyer,) Elsevier, Amsterdam, 2003, pp. 323 - 347
3. C. Silvestru, J. E. Drake, Coord. Chem. Rev. 2001, 223, 117 - 216
4. J. D. Woollins, J. Chem. Soc. Dalton Trans. 1996, 2893 - 2901.
5. Some exceptions that involve N-coordination have been reported, primarily for lanthanides
6. C. G. Pernin, J. A. Ibers, Inorg. Chem. 2000, 39, 1222 - 1226
7. C. G. Pernin, J. A. Ibers, Inorg. Chem. 2000, 39, 1216 - 1221
8. C. G. Pernin, J. A. Ibers, Inorg. Chem. 1999, 38, 5478 - 5483; and also for Pd
9. M. Necas, M. R. S. J. Foreman, J. Marek, J. D. Woollins, J. Novosad, New J. Chem. 2001, 25, 1256 - 1263.
10. J. Browning, K. R. Dixon, R. W. Hilts, Organometallics 1989, 8, 552 - 554.
11. T. Cantat, N. Mézailles, L. Ricard, Y. Jean, P. LeFloch, Angew. Chem. 2004, 116, 6542 - 6545
12. Angew. Chem. Int. Ed. 2004, 43, 6382 - 6385
13. T. Cantat, L. Ricard, Y. Jean, P. LeFloch, N. Mézailles, Organometallics 2006, 25, 4965 - 4976.
14. For a review, see:, T. Cantat, A. Auffrant, P. LeFloch, Dalton Trans. 2008, 1957 - 1972.
15. 2
16. IV
17. C. Foo, K-C. Lau, Y-F. Yang, C-W. So, Chem. Commun. 2009, 6816 - 6818.
18. IV:, T. Cantat, L. Ricard, N. Mézailles, P. LeFloch, Organometallics 2006, 25, 6030 - 6038.
19. II:, T. Cantat, M. Demange, N. Mézailles, L. Ricard, Y. Jean, P. LeFloch, Organometallics 2005, 24, 4838 - 4841.
20. III
21. III
22. T. Cantat, F. Jaroschik, F. Nief, L. Ricard, N. Mézailles, P. LeFloch, Chem. Commun. 2005, 5178 - 5180.
23. J.-C. Tourneux, J.-C. Berthet, P. Thuéry, N. Mézailles, P. LeFloch, M. Ephritikhine, Dalton Trans. 2010, 39, 2494 - 2496
24. T. Cantat, T. Arliguie, A. Noël, P. Thuéry, M. Ephritikhine, P. LeFloch, N. Mézailles, J. Am. Chem. Soc. 2009, 131, 963 - 972.
25. J. S. Ritch, T. Chivers, D. J. Eisler, H. M. Tuononen, Chem. Eur. J. 2007, 13, 4643 - 4653
26. T. Chivers, J. S. Ritch, S. D. Robertson, J. Konu, H. M. Tuononen, Acc. Chem. Res. 2010, 43, 1053 1062.
27. T. Cantat, X. Jacques, L. Ricard, X. LeGoff, N. Mézailles, P. LeFloch, Angew. Chem. 2007, 119, 6051 - 6054
28. Angew. Chem. Int. Ed. 2007, 46, 5947 - 5950.
29. J. Konu, T. Chivers, Chem. Commun. 2008, 4995 - 4997.
30. A. Davison, D. L. Reger, Inorg. Chem. 1971, 10, 1967 - 1970.
31. 2] with KOtBu in ethanol without significant cleavage of P-Se bonds:, P. Bhattacharyya, A. M. Z. Slawin, D. J. Williams, J. D. Woollins, J. Chem. Soc. Dalton Trans. 1995, 2489 - 2495.
32. J. Konu, H. M. Tuononen, T. Chivers, Inorg. Chem. 2009, 48, 11788 - 11798.
33. J. Konu, T. Chivers, Chem. Commun. 2010, 46, 1431 - 1433.
34. 2O;, D. Cauzzi, C. Graiff, M. Lanfranchi, G. Predieri, A. Tiripicchio, J. Chem. Soc. Chem. Commun. 1995, 2443 - 2444.
35. T. Cantat, F. Biaso, A. Momin, L. Ricard, M. Geoffroy, N. Mézailles, P. LeFloch, Chem. Commun. 2008, 874 - 876.
36. C.-P. Klages, J. Voss, Angew. Chem. 1977, 89, 744 - 745
37. Angew. Chem. Int. Ed. Engl. 1977, 16, 726 - 727
38. Angew. Chem. 1977, 89, 744 - 745
39. D. Helling, C.-P. Klages, J. Voss, J. Phys. Chem. 1980, 84, 3638 - 3646
40. A. G. Davies, A. G. Neville, J. Chem. Soc. Perkin Trans. 2 1992, 171 - 173.
41. 2CSe in which R is a C-bonded substituent; if one or both of the R groups involves a heteroatom bonded to the three-coordinate carbon, these derivatives are referred to as selones or selenocarbonyl compounds. For a review, see, T. Murai, S. Kato, Top. Curr. Chem. 2000, 208, 178 - 199
42. T. Murai, R. Hori, T. Maruyama, F. Shibahar, Organometallics 2010, 29, 2400 - 2402.
43. [6a]
44. J. D. Lee, M. W. R. Bryant, Acta Crystallogr. Sect. B 1969, 25, 2094 - 2101
45. M. Sacerdoti, G. Gilli, P. Domiano, Acta Crystallogr. Sect. A 1975, 31, 327 - 329
46. C. M. Woodard, D. S. Brown, J. D. Lee, A. G. Massey, J. Organomet. Chem. 1976, 121, 333 - 344
47. J. S. Ricci, I. Bernal, J. Am. Chem. Soc. 1969, 91, 4078 - 4082
48. E. Delgado, E. Hernandez, N. Mansilla, F. Zamora, L. A. Martinez-Cruz, Inorg. Chim. Acta 1999, 284, 14 - 19
49. R. Marsh, Acta Crystallogr. 1952, 5, 458 - 462
50. G. D. Morris, F. W. B. Einstein, Acta Crystallogr. Sect. C 1986, 42, 1433 - 1435
51. P. M. Dickson, M. A. D. McGowan, B. Yearwood, M. J. Heeg, J. P. Oliver, J. Organomet. Chem. 1999, 588, 42 - 50.
52. 3:, P. J. Ruiz, M. Ceroni, O. V. Quinzani, V. Riera, M. Vivanco, S. Garcia-Granda, F. VanderMaelen, M. Lanfranchi, A. Tiripicchio, Chem. Eur. J. 2001, 7, 4422 - 4430.
53. J. Ruiz, R. Araz, M. Ceroni, M. Vivanco, J. F. VanderMaelen, S. García-Granda, Organometallics 2010, 29, 3058 3061.
54. 2] 8-b } (see the Experimental Section).
55. S. O. Grim, E. D. Walton, Inorg. Chem. 1980, 19, 1982 - 1987.
56. [29] The results of these experiments are summarised in the Supporting Information.
57. R. T. Boeré, A. M. Bond, T. Chivers, S. W. Feldberg, T. L. Roemmele, Inorg. Chem. 2007, 46, 5596 - 5607.
58. C. A. Bayse, E. R. Rafferty, Inorg. Chem. 2010, 49, 5365 - 5367.
59. 6] resulted in decomposition.
60. 2], a selenium adduct of hexaphenylcarbodiphosphorane, exhibits a very long C-Se bond of about 1.99Å and significant retention of double bond character in the PCP unit:, H. Schmidbaur, C. E. Zybill, D. Neugebauer, Angew. Chem. 1982, 94, 321 - 322
61. Angew. Chem. Int. Ed. Engl. 1982, 21, 310 - 311.
62. W.-W. duMont, S. Kubiniok, K. Peters, H.-G. vonSchnering, Angew. Chem. 1987, 99, 820 - 821
63. Angew. Chem. Int. Ed. Engl. 1987, 26, 780 - 781
64. J. Jeske, P. G. Jones, A. Martens-vonSalzen, W.-W. dMont, Acta Crystallogr. Sect. E 2002, 58, o 350 -o 352.
65. L. Pauling, The Nature of the Chemical Bond, 3 rd ed., Cornell University Press, Ithaca, 1960.
66. F. Cristiani, F. Demartin, F. A. Devillanova, F. Isaia, V. Lippolis, G. Verani, Inorg. Chem. 1994, 33, 6315 - 6324.
67. A. Panda, G. Mugesh, H. B. Singh, R. J. Butcher, Organometallics 1999, 18, 1986 - 1992
68. G. Mugesh, A. Panda, H. B. Singh, R. J. Butcher, Chem. Eur. J. 1999, 5, 1411 - 1421.
69. K. Okuma, K. Kojima, I. Kaneko, Y. Tsujimoto, H. Ohta, Y. Yokomori, J. Chem. Soc. Perkin Trans. 1 1994, 2151 - 2159
70. P. R. Brooks, J. A. Counter, R. Bishop, E. R. T. Tiekink, Acta Crystallogr. Sect. C 1991, 47, 1939 - 1941.
71. S. Husebye, S. V. Lindeman, M. D. Rudd, Acta Crystallogr. Sect. C 1997, 53, 809 - 811.
72. [24] However, the hydrogen atom in the PC(H)P unit was located from the Fourier density map of the crystal structures and it was refined. We also draw attention to the excellent agreement between the experimental and calculated bond parameters of the anion 8-b (Table4).
73. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865 - 3868
74. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396
75. J. P. Perdew, K. Burke, M. Ernzerhof, J. Chem. Phys. 1996, 105, 9982 - 9985
76. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158 - 6170.
77. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829 - 5835.
78. Gaussian03, Revision C.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery,Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, 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, C. Gonzalez, J.A. Pople Gaussian, Inc., Pittsburgh, PA, 2003.
79. TURBOMOLE 6.1, Program Package for ab initio Electronic Structure Caluclations, Theoretical Chemistry Group, University of Karlsruhe, Karlsruhe, 2009.
80. L. J. Laaksonen, J. Mol. Graphics 1992, 10, 33 - 34
81. D. L. Bergman, L. J. Laaksonen, A. Laaksonen, J. Mol. Graphics Modell. 1997, 15, 301 - 306.
82. SHELXS-97, Program for Crystal Structure Determination, G.M. Sheldrick, University of Göttingen, Göttingen, 1997.
83. SHELXL-97, Program for Crystal Structure Refinement, G.M. Sheldrick, University of Göttingen, Göttingen, 1997.