QTAIM analysis of ligand properties and mechanisms of tuning of 6-membered ring N-heterocyclic carbenes in transition metal complexes through ring-substituent variation

Journal of Physical Chemistry A

Volumn 113, Issue 30, 2009, Pages 8647-8653

  Johnson, Lucius E ^a   DuPré, Donald B ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6-MEMBERED RINGS; AMINO-SUBSTITUTION; ATOMIC PROPERTIES; BACK-DONATION; C-O STRETCHING; CARBENE; CARBONYL GROUPS; CHARGE CONCENTRATION; EHRENFEST; ELECTRON DENSITIES; INTERATOMIC SURFACES; LIGAND PROPERTIES; N-HETEROCYCLIC CARBENES; POTENTIAL ENERGY DENSITY; QUANTUM THEORY OF ATOMS IN MOLECULES; STATIONARY STATE; VALENCE SHELLS;

AMINES; ATOMS; BORON; BORON COMPOUNDS; COBALT; COBALT COMPOUNDS; ELECTRIC CHARGE; LIGANDS; METAL COMPLEXES; QUANTUM THEORY; TUNING;

METALS;

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; METHANE; ORGANOMETALLIC COMPOUND; TRANSITION ELEMENT;

ARTICLE; CHEMISTRY; QUANTUM THEORY;

HETEROCYCLIC COMPOUNDS; LIGANDS; METHANE; ORGANOMETALLIC COMPOUNDS; QUANTUM THEORY; TRANSITION ELEMENTS;

EID: 67651166797     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp901533g     Document Type: Article

References (46)

1. (a) Öfele, K. J. Organomet. Chem. 1968, 12, P42-P43.
2. (b) Wanzlick, H.-W.; Schönherr, W. Angew. Chem., Int. Ed. 1968, 7, 141-142.
3. Arduengo, A. J., III.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
4. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
5. Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883.
6. Crudden, C. M.; Allen, D. P. Coord, Chem. Rev. 2004, 248, 2247-2273.
7. Cavallo, L.; Correa, A.; Costabile. C: Jacobsen. H. J. Organomet. Chem. 2005, 690, 5407-5413.
8. Alder, R. W.; Blake, M. E.; Chaker, L.; Harvey, J. N.; Paolini, F.; Schutz, J. Angew. Chem., Int. Ed. 2004, 43, 5896-5911.
9. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130-5135.
10. (a) Perry, M. C.; Burgess, K. Tetrahedron Asym. 2003, 14, 951-961.
11. (b) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70-80.
12. Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439-441.
13. Präsang, C.; Donnadieu, B.; Bertrand, G. J. Am. Chem. Soc. 2005, 127, 10182-10183.
14. Schoeller, W. W.; Frey, G. D.; Bertrand, G. Chem.-Eur. J. 2008, 14, 4711-4718.
15. Kausamo, A.; Tuononen, H. M.; Krahulic, K. E.; Roesler, R. Inorg. Chem. 2008, 47, 1145-1154.
16. Jacobsen, H.; Correa, A.; Costabile, C.; Cavallo, L. J. Organomet. Chem. 2006, 691, 4350-4358.
17. Ishida, Y.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13585-13588.
18. Schoeller, W. W.; Eisner, D.; Grigoleit, S.; Rozhenko, A. B.; Alijah, A. J. Am. Chem. Soc. 2000, 122, 10115-10120.
19. Tafipolsky, M.; Scherer, W.; Ofele, K.; Artus, G.; Pedersen, B.; Herrmann, W. A.; McGrady, G. S. J. Am. Chem. Soc. 2002, 124, 5865-5880.
20. Lavallo, V.; Canac, Y.; Präsang, C.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2005, 44, 5705-5709.
21. Leuthäußer, S.; Schwarz, D.; Plenio, H. Chem.-Eur. J. 2007, 13, 1195-7203.
22. Jacobsen, H.; Correa, A.; Poater, A.; Costabile, C.; Cavallo, L. Coord. Chem. Rev. 2009, 253, 687-703.
23. Frenking, G.; Sola, M.; Vvboishchikov, S. F. J. Organomet. Chem. 2005, 690, 6178-6204.
24. Johnson, L. E.; DuPré, D. B. J. Phys. Chem. A 2007, 111, 11066-11073.
25. Johnson, L. E.; DuPré, D. B. J. Phys. Chem. A 2008, 112, 7448-7454.
26. (a) Bader, R. F. W. Atoms in molecules. A quantum theory; Clarendon Press: Oxford, U.K., 1990.
27. (b) Bader, R. F. W.; Fang, D.-C. J. Chem. Theory. Comput. 2005, 1, 403-414.
28. (c) Bader, R. F. W. Int J. Quantum Chem. 2003, 94, 173-177.
29. Poater, J.; Cases, M.; Fradera, X.; Duran, M.; Solà, M. Chem. Phys. 2003, 294, 129-139.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789.
32. Frisch, M. J.; et al. Gaussian03, revision E.01; Gaussian, Inc.; Wallingford, CT, 2004.
33. Biegler-Konig, F.; Schonbohm, J. J. Comput. Chem. 2002, 23, 1489-1494.
34. Fradera, X.; Austen, M. A.; Bader, R. F. W. J. Phys. Chem. A. 1999, 103, 304-314.
35. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0 Program Manual. Natural Bond Orbital Analysis Programs, NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001.
36. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1 Program Manual. Theoretical Chemistry Institute and Department of Chemistry: University of Wisconsin: Madison, Wl, 1990.
37. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842-3888, and references therein.
38. Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
39. Wolinksi, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
40. Vidal, I.; Melchor, S.; Dobado, J. A. J. Phys. Chem. A 2005, 109, 7500-7508.
41. Cortés-Guzmán, F.; Bader, R. F. W. Coord. Chem. Rev. 2005, 249, 633-662.
42. MacDougall, P. J.; Bader, R. F. W. Can. J. Chem. 1986, 64, 1496-1508.
43. MacDougall, P. J.; Hall, M. B. Trans. Am. Cryst. Assoc. 1993, 26, 105-123.
44. MacDougall, P. J.; Hall, M. B.; Bader, R. F. W.; Cheeseman, J. R. Can. J. Chem. 1989, 67, 1842-1846.
45. Wiberg, K. B.; Hammer, J. D.; Keith, T. A.; Zilm, K. J. Phys. Chem. A 1999, 103, 21-27.
46. Ramsey, N. F. Phys. Rev. 1950, 78, 699.