Synthesis and structure of carbene-stabilized N-centered cations [L 2N]+, [L2NR]2+, [LNR 3]2+, and [L3N]3+

Chemistry - A European Journal

Volumn 19, Issue 11, 2013, Pages 3542-3546

  Kozma, Ágnes ^a   Gopakumar, Gopinadhanpillai ^a   Farès, Christophe ^a   Thiel, Walter ^a   Alcarazo, Manuel ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

carbenes; cyclopropenylidenes; density functional calculations; electrochemistry; N centered cations

Indexed keywords

AMINES; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRONIC STRUCTURE; POSITIVE IONS;

CARBENES; CHEMICAL ENVIRONMENT; CYCLOPROPENYLIDENES; GAIN INSIGHT; NITROGEN ATOM;

CYCLIC VOLTAMMETRY;

EID: 84874600925     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204186     Document Type: Article

References (40)

1. K.-O. Feldmann, J. J. Weigand, Angew. Chem. Int. Ed. 2012, 51, 6566
2. K. O. J. L. Dutton, P. J. Ragogna, Coord. Chem. Rev. 2011, 255, 1414
3. C. A. Dyker, N. Burford, Chem. Asian J. 2008, 3, 28
4. B. D. Ellis, C. L. B. Macdonald, Coord. Chem. Rev. 2007, 251, 936
5. N. Burford, P. J. Ragogna, J. Chem. Soc., Dalton Trans. 2002, 4307.
6. I. Bernhardi, T. Drews, K. Seppelt, Angew. Chem. 1999, 111, 2370
7. Angew. Chem. Int. Ed. 1999, 38, 2232
8. R. A. Kunetskiy, I. Cisařova, D. Šaman, I. M. Lyapkalo, Chem. Eur. J. 2009, 15, 9477.
9. F. Ramirez, N. B. Desai, B. Hansen, N. McKelvie, J. Am. Chem. Soc. 1961, 83, 3539
10. R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3260
11. R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3273
12. R. Tonner, G. Frenking, Angew. Chem. 2007, 119, 8850
13. Angew. Chem. Int. Ed. 2007, 46, 8695
14. R. Tonner, F. Öxler, B. Neumüller, W. Petz, G. Frenking, Angew. Chem. 2006, 118, 8206
15. Angew. Chem. Int. Ed. 2006, 45, 8038
16. C. A. Dyker, V. Lavallo, B. Donnadieu, G. Bertrand, Angew. Chem. 2008, 120, 3250
17. Angew. Chem. Int. Ed. 2008, 47, 3206
18. C. A. Dyker, G. Bertrand, Nat. Chem. 2009, 1, 265
19. M. Alcarazo, C. W. Lehmann, A. Anoop, W. Thiel, A. Fürstner, Nat. Chem. 2009, 1, 295
20. A. Fürstner, M. Alcarazo, R. Goddard, C. W. Lehmann, Angew. Chem. 2008, 120, 3254
21. Angew. Chem. Int. Ed. 2008, 47, 3210.
22. R. Weiss, S. Engel, Synthesis 1991, 1077
23. G. Bouhadir, R. W. Reed, R. Réau, G. Bertrand, Heteroat. Chem. 1995, 6, 371.
24. J. Petuškova, M. Patil, S. Holle, C. W. Lehmann, W. Thiel, M. Alcarazo, J. Am. Chem. Soc. 2011, 133, 20758
25. J. Carreras, M. Patil, W. Thiel, M. Alcarazo, J. Am. Chem. Soc. 2012, 134, 16753
26. 3+ species, see Ref. [4a,b]. For the isolation of 2,3-bis(diisopropylamino)cyclopropenyl-1- ylidene, see
27. V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2006, 312, 722.
28. CCDC 911773 (2), 911774 (5 TfO), 911775 (15), 911776 (11), and 911777 (4) 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.
29. M. A. Celik, R. Sure, S. Klein, R. Kinjo, G. Bertrand, G. Frenking, Chem. Eur. J. 2012, 18, 5676. See also
30. I. S. K. Kerkines, A. Papakondylis, A. Mavridis, J. Phys. Chem. A 2002, 106, 4435.
31. R. A. Kunetskiy, S. M. Polyakova, J. Vavřik, I. Císařová, J. Saame, E. R. Nerut, I. Koppel, I. A. Koppel, A. Kütt, I. Leito, I. M. Lyapkalo, Chem. Eur. J. 2012, 18, 3621.
32. H. Bruns, M. Patil, J. Carreras, A. Vázquez, W. Thiel, R. Goddard, M. Alcarazo, Angew. Chem. 2010, 122, 3762
33. Angew. Chem. Int. Ed. 2010, 49, 3680. For the phosphorus analogue of 6, see
34. J. J. Weigand, N. Burford, A. Decken, A. Schulz, Eur. J. Inorg. Chem. 2007, 4868.
35. R. Kinjo, B. Donnadieu, M. A. Celick, G. Frenking, G. Bertrand, Science 2011, 333, 610.
36. B. D. Ellis, C. A. Dyer, A. Decken, C. L. B. Macdonald, Chem. Commun. 2005, 1965
37. N. Burford, P. J. Ragogna, J. Chem. Soc., Dalton Trans. 2002, 4307
38. J. J. Weigand, K. Feldmann, F. D. Henne, J. Am. Chem. Soc. 2010, 132, 16321
39. M. Azouri, J. Andrieu, M. Picquet, H. Cattey, Inorg. Chem. 2009, 48, 1236.
40. G. H. Colemann, W. A. Noyes, J. Am. Chem. Soc. 1921, 43, 2211.