Mechanisms of intramolecular rearrangements of cyclic siloxycarbenes

Journal of Physical Chemistry A

Volumn 108, Issue 21, 2004, Pages 4694-4706

  Loncke, Paul G ^a   Peslherbe, Gilles H ^a  

^a Dept of Electrical and Computer Engineering   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BIFURCATION (MATHEMATICS); CARRIER CONCENTRATION; ENTHALPY; FERMENTATION; MOLECULAR STRUCTURE; PHOTOLYSIS; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; REACTION KINETICS; SILICON; THERMODYNAMICS;

ELECTRON LOCALIZATION FUNCTION; INTRAMOLECULAR REARRANGEMENTS; NUCLEOPHILIC ATTACK; RING CONTRACTION;

MOLECULAR DYNAMICS;

EID: 2942594060     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0494281     Document Type: Article

References (60)

1. Foster, A. M.; Agosta, W. C. J. Am. Chem. Soc. 1972, 94, 5777.
2. Foster, A. M.; Agosta, W. C. J. Am. Chem. Soc. 1973, 95, 608.
3. Ayral-Kaloustian, S.; Agosta, W. C. J. Org. Chem. 1982, 47, 284.
4. Yates, P.; Loutfy, R. O. Acc. Chem. Res. 1975, 8, 209.
5. Yates, P.; Tam, J. C. J. Chem. Soc., Chem. Commun. 1975, 737.
6. Umbricht, G.; Hellman, M. D.; Hegedus, L. S. J. Org. Chem. 1998, 63, 5173.
7. Switlak, K.; He, D.; Yates, P. J. Chem. Soc., Perkin Trans. 1 1992, 2579.
8. Loncke, P. G., Ph.D. Thesis, Concordia University, 2004.
9. Loncke, P. G.; Gadosy, T. A.; Peslherbe, G. H. Can. J. Chem. 2002, 80, 302.
10. Loncke, P. G.; Gadosy, T. A.; Peslherbe, G. H. Arkivok 2001, 2, 179.
11. Pezacki, J. P.; Loncke, P. G.; Ross, J. P.; Warkentin, J.; Gadosy, T. A. Org. Lett. 2000, 2, 2733.
12. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
13. Brook, A. G.; Pearce, R.; Pierce, J. B. Can. J. Chem. 1971, 49, 1622.
14. Duff, J. M.; Brook, A. G. Can. J. Chem. 1973, 31, 2869.
15. Hassner, A.; Soderquist, J. A. Tetrahedron Lett. 1980, 21, 429.
16. Moss, R. A. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press Inc.: Greenwich, CT, 1994; Vol. 1, p 59.
17. Liu, M. T. H. Acc. Chem. Res. 1994, 21, 287.
18. Schaefer, H. F. Acc. Chem. Res. 1979, 12, 288.
19. Hoffmann, R.; Zeiss, G. D.; Dine, G. W. V. J. Am. Chem. Soc. 1968, 90, 1485.
20. Evanseck, J. D.; Houk, K. N. J. Phys. Chem. 1990, 94, 5518.
21. Evanseck, J. D.; Mareda, J.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 73.
22. Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17.
23. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
24. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: Ltd.: Chichester, 1976.
25. Fukui, K. Science 1982, 218, 747.
26. Rauk, A. Orbital Interaction Theory of Organic Chemistry, 2nd ed.; Wiley-Interscience: New York, 2001.
27. Gilchrist, T. L.; Storr, R. C. Organic Reactions and Orbital Symmetry, 2nd ed.; Cambridge University Press: London, 1979.
28. Selection rules for 1,2-sigmatropic rearrangements also indicate that this rearrangement mechanism is symmetry forbidden since it involves a four-electron (or 4n) antiaromatic transition state. For similar rearrangements in carbanions, see, e.g., Grovenstein, Angew. Chem., Int. Ed. Engl. 1978, 17, 313.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
30. Jensen, F. Introduction to Computational Chemistry; John Wiley & Sons Ltd.: Baffins Lane, 1999.
31. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
32. 2〉 is greater than 0 to ensure that we did indeed obtain the open-shell solutions.
33. Grafenstein, J.; Kraka, E.; Filatov, M.; Cremer, D. Int. J. Mol. Sci. 2002, 3, 360.
34. Perdew, J. P. Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
35. Perdew, J. P.; Ernzerhof, M.; Burke, K. J. Chem. Phys. 1996, 105, 9982.
36. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.4: Gaussian, Inc.: Pittsburgh, PA, 1998.
38. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
39. Bannerjee, A.; Adams, N.; Simons, J.; Shepard, R. J. Phys. Chem. 1985, 89, 52.
40. Simons, J.; Jorgensen, P.; Taylor, H.; Ozment, J. J. Phys. Chem. 1983, 87, 2745.
41. Cerjan, C. J.; Miller, W. H. J. Chem. Phys. 1981, 75, 2800.
42. Ochterski, J. W. Thermochemistry in Gaussian; Gaussian Inc.: Pittsburgh, PA, 2000.
43. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Clarendon Press: Oxford, 1990.
44. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 539.
45. Silvi, B.; Savin, A. Nature 1994, 371, 683.
46. Savin, A.; Nesper, R.; Wengert, S.; Fassler, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1809.
47. Noury, S.; Colonna, F.; Savin, A.; Silvi, B. J. Mol. Struct. 1998, 450, 59.
48. Savin, A.; Silvi, B.; Colonna, F. Can. J. Chem. 1996, 74, 1088.
49. The AIMPAC suite of programs is available from Professor R. F. W. Bader, McMaster University, Canada and from the AIMPAC website (www.chemistry.mcmaster. ca/aimpac).
50. Biegler-Konig, F. W.; Bader, R. F. W.; Tang, T. J. Comput. Chem. 1982, 3, 317.
51. Biegler-König, F.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545.
52. Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. TopMod Package; Université Pierre et Marie Curie: Paris, 1997.
53. SciAn is a free scientific visualization and animation program for high-performance graphic workstations developed by E. Pepke, J. Murray, J. Lyons, and Y. Hwu that can be obtained from the CCL website (www.ccl.net/cca/ software/AIX/index.shtml).
54. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
55. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 3.0 Program Manual; Theoretical Chemistry Institute and Department of Chemistry. University of Wisconsin: Madison. Wisconsin.
56. Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F.; Hadad, C. M. J. Am. Chem. Soc. 1997, 119, 5682.
57. Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 9148.
58. Kyba, E. P.; John, A. M. J. Am. Chem. Soc. 1977, 99, 8329.
59. Press, L. S.; Shechter, H. J. Am. Chem. Soc. 1979, 101, 509.
60. Kyba, E. P. J. Am. Chem. Soc. 1977, 99, 8330.