Dynamics of carbene cycloadditions

Journal of the American Chemical Society

Volumn 133, Issue 44, 2011, Pages 17848-17854

  Xu, Lai ^a   Doubleday, Charles E ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIEXPONENTIAL DECAY; BOND FORMATION; CARBENES; CONCERTED REACTIONS; CYCLOADDITIONS; DIRADICALS; EXACT EXCHANGE; GAUSSIANS; NONLINEAR APPROACH; QUANTUM MECHANICAL ENERGY; QUASICLASSICAL TRAJECTORY CALCULATIONS; REACTIVE TRAJECTORIES; TIME GAP;

ETHYLENE; HYDROCARBONS; QUANTUM THEORY; TRAJECTORIES;

CYCLOADDITION;

ALKENE; CARBENE; ETHYLENE; MONOCYTE CHEMOTACTIC PROTEIN 1;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; GEOMETRY; MOLECULAR DYNAMICS; QUANTUM MECHANICS;

CYCLIZATION; METHANE; QUANTUM THEORY;

EID: 80455123869     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207051b     Document Type: Article

References (56)

1. Hine, J. J. Am. Chem. Soc. 1950, 72, 2438-2445
2. Doering, W.; von, E.; Hoffmann, A. K. J. Am. Chem. Soc. 1954, 76, 6162-6165
3. Skell, P. S.; Garner, A. Y. J. Am. Chem. Soc. 1956, 78, 5430-5433
4. Moore, W. R.; Moser, W. R.; LaPrade, J. E. J. Org. Chem. 1963, 28, 2200
5. Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 1475
6. Zurawski, B.; Kutzelnigg, W. J. Am. Chem. Soc. 1978, 100, 2654-2659
7. Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770
8. Houk, K. N.; Rondan, N. G.; Mareda, J. J. Am. Chem. Soc. 1984, 106, 4291-4293
9. Blavins, J. J.; Cooper, D. L.; Karadakov, P. B. Int. J. Quantum Chem. 2004, 98, 465
10. Merrer, D. C.; Rablen, P. R. J. Org. Chem. 2005, 70, 1630
11. Lecea, B.; Ayerbe, M.; Arrieta, A.; Cosso, F. P.; Branchadell, V.; Ortuo, R. M.; Baceiredo, A. J. Org. Chem. 2007, 72, 357
12. Joo, H.; Kraka, E.; Quapp, W.; Cremer, D. Mol. Phys. 2007, 105, 2697-2717
13. Kraka, E.; Cremer, D. Acc. Chem. Res. 2010, 43, 591-601
14. Gao, X.; Ohtsuka, Y.; Ishimura, K.; Nagase, S. J. Phys. Chem. A 2009, 113, 9852-9860
15. Keating, A. E.; Merrigan, S. R.; Singleton, D. A.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 3933-3938
16. Chapman, S.; Bunker, D. L. J. Chem. Phys. 1975, 62, 2890
17. Muckerman, J. T. Theoretical Chemistry; Academic Press: New York, 1981; Vol. 6, part A, Chapter 1.
18. Truhlar, D. G.; Duff, J. W.; Blais, N. C.; Tully, J. C.; Garrett, B. C. J. Chem. Phys. 1982, 77, 764
19. Peslherbe, G. H.; Wang, H.; Hase, W. L. J. Am. Chem. Soc. 1996, 118, 2257
20. Peslherbe, G. H.; Hase, W. L. J. Chem. Phys. 1996, 104, 7882
21. Debbert, S. J.; Carpenter, B. K.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 7896-7897
22. Vayner, G.; Addepalli, S. V.; Song, K.; Hase, W. L. J. Chem. Phys. 2006, 125, 14317
23. Wang, I. S. Y.; Karplus, M. J. Am. Chem. Soc. 1973, 95, 8160-8164
24. Xu, L.; Doubleday, C. E.; Houk, K. N. Angew. Chem., Int. Ed. 2009, 48, 2746-2748
25. Xu, L.; Doubleday, C. E.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 3029-3037
26. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
27. Hase, W. L.; Duchovic, R. J.; Hu, X.; Komornicki, A.; Lim, K.; Lu, D.-H.; Peslherbe, G. H.; Swamy, K. N.; Vande Linde, S. R.; Wang, H.; Wolfe, R. J. VENUS 96 QCPE 1996; p 671.
28. Chapman, S.; Bunker, D. L. J. Chem. Phys. 1975, 62, 2890-2899
29. Peslherbe, G. H.; Wang, H.; Hase, W. L. Adv. Chem. Phys. 1999, 105, 171-201
30. Doubleday, C.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648-3658
31. Frisch, M. J.; et al. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009. Full reference can be found in the Supporting Information.
32. Truhlar, D. G.; Garrett, B. C.; Klippenstein, S. J. J. Phys. Chem. 1996, 100, 12771-12800
33. Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 4293-4294
34. Bernardi, F.; Bottoni, A.; Canepa, C.; Olivucci, M.; Robb, M. A.; Tonachini, G. J. Org. Chem. 1997, 62, 2018 and references therein
35. Pedersen, S.; Herek, J. L.; Zewail, A. H. Science 1994, 266, 1359
36. See also a dynamics simulation of the trimethylene diradical: Doubleday, C.; Bolton, K.; Peslherbe, G. H.; Hase, W. L. J. Am. Chem. Soc. 1996, 118, 9922-9931
37. Kafafi, S.; Hudgens, J. W. J. Phys. Chem. 1989, 93, 3474-3479
38. Fudacz, P. S.; Dober, J. D.; Jarman, D. L.; Standard, J. M.; Quandt, R. W. J. Phys. Chem. A 2003, 107, 9730-9735
39. Wei, H.; Hrovat, D. A.; Dolbier, W. R., Jr.; Smart, B. E.; Borden, W. T. Angew. Chem., Int. Ed. 2007, 46, 2666-2668
40. Doubleday, C; Bolton, K; Peslherbe, G. H.; Hase, W. L. J. Am. Chem. Soc. 1996, 118, 9922-9931
41. Doubleday, C. J. Phys. Chem. A 2001, 105, 6333-6341
42. Doubleday, C.; Suhrada, C. P.; Houk, K. N. J. Am. Chem. Soc. 2006, 128, 90-94
43. Carpenter, B. K. Angew. Chem., Int. Ed. 1998, 37, 3340-3350
44. Carpenter, B. K. Acc. Chem. Res. 1992, 25, 520-528
45. Mitsch, R. A. J. Am. Chem. Soc. 1965, 87, 758-761
46. Xu, L.; Doubleday, C. E.; Houk, K. N., unpublished results.
47. Firestone, R. A. J. Org. Chem. 1968, 33, 2285-2290
48. Vayner, G.; Addepalli, S. V.; Song, K.; Hase, W. L. J. Chem. Phys. 2006, 125, 014317
49. Huang, C.; Tasi, L.; Hu, W. J. Phys. Chem. A 2001, 105, 9945-9953
50. Aktah, D.; Passerone, D.; Parrinello, M. J. Phys. Chem. A 2004, 108, 848-854
51. Kelly, E.; Seth, M.; Ziegler, T. J. Phys. Chem. A 2004, 108, 2167-2180
52. Nao Noguchi, N.; Nakano, H. J. Chem. Phys. 2009, 130, 154309-1-11
53. Black, K.; Liu, P.; Xu, L.; Doubleday, C. E.; Houk, K. N., unpublished results.
54. Thomas, J. B.; Waas, J. R.; Harmata, M.; Singleton, D. A. J. Am. Chem. Soc. 2008, 130, 14544-14555
55. Wang, Z. H.; Hirschi, J. S.; Singleton, D. A. Angew. Chem., Int. Ed. 2009, 48, 9156-9159
56. Glowacki, D. R.; Marsden, S. P.; Pilling, M. J. J. Am. Chem. Soc. 2009, 131, 13896-13897