β-Fragmentation of tertiary alkoxyl radicals: G3(MP2)-RAD and natural bond orbital investigations

ChemPhysChem

Volumn 13, Issue 3, 2012, Pages 703-707

  Marque, Sylvain R A ^a   Siri, Didier ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

computational chemistry; density functional calculations; fragmentation reactions; hyperconjugation; radicals

Indexed keywords

COMPUTATIONAL CHEMISTRY; DENSITY FUNCTIONAL THEORY;

ALKOXYL RADICALS; BOND CLEAVAGES; DFT CALCULATION; FRAGMENTATION REACTIONS; HYPERCONJUGATION; LONE-PAIR EFFECTS; NATURAL BOND ORBITAL; RADICALS;

CHEMICAL BONDS;

EID: 84857272734     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.201100708     Document Type: Article

References (28)

1. G. Moad, D. H. Solomon, The Chemistry of Radical Polymerization 2nd edition, Elsevier Amsterdam, 2006.
2. Radicals in Organic Synthesis (Eds.:, P. Renaud and M. Sibi,), Wiley-VCH, 2001; Vol. 1 &2.
3. J. K. Kochi, Free Radicals, vols. 1&2, Wiley-VCH, New York, 1973.
4. O. M. Zarechnaya, I. A. Opeida, A. F. Dmitruk, Russ. J. Org. Chem. 2001, 37, 1405-1408.
5. A. Rauk, R. J. Boyd, S. L. Boyd, D. J. Henry, L. Radom, Can. J. Chem. 2003, 81, 431-442.
6. T. S. Dibble, J. Phys. Chem. A 1999, 103, 8559-8565.
7. S. Wilsey, P. Dowd, K. N. Houk, J. Org. Chem. 1999, 64, 8801.
8. H. Somnitz, R. Zellner, Phys. Chem. Chem. Phys. 2000, 2, 1907.
9. R. Méreau, M.-T. Rayez, F. Caralp, J.-C. Rayez, Phys. Chem. Chem. Phys. 2000, 2, 1919-1928.
10. H. Somnitz, R. Zellner, Phys. Chem. Chem. Phys. 2000, 2, 4319.
11. R. Méreau, M.-T. Rayez, J.-C. Rayez, P. C. Hiberty, Phys. Chem. Chem. Phys. 2001, 3, 3656-3661.
12. T. S. Dibble, J. Am. Chem. Soc. 2001, 123, 4228-4234.
13. G. P. F. Wood, A. Rauk, L. Radom, J. Phys. Chem. Theory Comput. 2005, 1, 889-899.
14. G. P. F. Wood, C. J. Easton, A. Rauk, M. J. Davies, L. Radom, J. Phys. Chem. A 2006, 110, 10316-10323.
15. F. Weinhold, Encyclopedia of Computational Chemistry, John Wiley & Sons, Inc., Chichester UK, 1998, pp. 1792-1811.
16. M. Leblanc, D. Siri, S. R. A. Marque, S. Grimaldi, D. Bertin, P. Tordo, Int. J. Quantum Chem. 2006, 106, 676-685.
17. G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334-338.
18. E. I. Izgorodina, D. R. B. Brittain, J. L. Hodgson, E. H. Krenske, C. Y. Lin, M. Namazian, M. L. Coote, J. Phys. Chem. A 2007, 111, 10754-10768.
19. E. I. Izgorodina, M. L. Coote, Chem. Phys. 2006, 324, 96-110.
20. A. G. Baboul, L. A. Curtiss, P. C. Redfern, K. J. Raghavachari, J. Chem. Phys. 1999, 110, 7650-7657.
21. Gaussian 09 (Revision A.02), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford, CT, 2009.
22. M. Weber, H. Fischer, J. Am. Chem. Soc. 1999, 121, 7381-7388.
23. For 1 b:, S. Navarre, B. Maillard, J. Polym. Sci. Polym. Chem. Ed. 2000, 38, 2957-2963; For 1 c
24. S. Suyama, Y. Watanabe, Y. Sawaki, Bull. Chem. Soc. Jpn. 1990, 63, 716-720.
25. T. Nakamura, Y. Watanabe, S. Suyama, H. Tezuka, J. Chem. Soc. Perkin Trans. 2 2002, 1364-1369.
26. E. Juaristi, G. Cuevas, The Anomeric Effect, CRC Press, Boca Raton, FL, 1995.
27. C. J. Cramer, Essentials of Computational Chemistry, Theories and Models, John Wiley & Sons, Ltd, Chichester, 2002, pp. 523-524.
28. F. Weinhold, Abstracts of Papers, 226th ACS National Meeting, New York 2003, ORGN-663.