Mechanism of electrocyclic ring-opening of diphenyloxirane: 40 Years after Woodward and Hoffmann

Chemistry - A European Journal

Volumn 15, Issue 41, 2009, Pages 10825-10829

  Friedrichs, Jana ^a   Frank, Irmgard ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Density functional calculations; Molecular dynamics; Photochemistry; Reaction mechanisms; Ring opening reactions

Indexed keywords

DENSITY FUNCTIONAL CALCULATIONS; ELECTROCYCLIC RINGS; FIRST EXCITED STATE; FIRST-PRINCIPLES; MOLECULAR DYNAMICS SIMULATIONS; ON-THE-FLY; OXIRANES; PHOTOCHEMISTRY; REACTION MECHANISMS; RING-OPENING REACTIONS; WOODWARD;

AROMATIC HYDROCARBONS; DYNAMICS; ELECTRONIC STRUCTURE; MOLECULAR DYNAMICS; POTENTIAL ENERGY; REACTION KINETICS; SOLID STATE PHYSICS; SULFUR COMPOUNDS;

DENSITY FUNCTIONAL THEORY;

EID: 70350223590     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901152     Document Type: Article

References (29)

1. R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 395.
2. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797;
3. Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
4. F. Volatron, N. T Anh, Y. Jean, J. Am. Chem. Soc. 1983, 705, 2359-2364.
5. F. Cordova, L. J. Doriol, A. Ipatov, M. E. Casida, C. Filippi, A. Vela, J. Chem. Phys. 2007, 127, 164111.
6. "It may perhaps be appropriate here to emphasise that the central content of the principle lies in the incontrovertible proposition that a chemical reaction will proceed the more readily, the more bonding may be maintained throughout the transformation. [..] Since every elementary step in any chemical reaction is a concerted process, correlative ideas must be applicable to all reactions." R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797;
7. Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
8. R. Gomer, W. A. Noyes Jr., J. Am. Chem. Soc. 1950, 72, 101.
9. A. M. Trozzolo, WA. Yager, G. W. Griffin, H. Kristinsson, I. Sarkar, J. Am. Chem. Soc. 1967, 89, 3357.
10. P. C. Petrellis, H. Dietrich, E. Meyer, G. W. Griffin, J. Am. Chem. Soc. 1967, 89, 1967.
11. G. W. Griffin, Angew. Chem. 1971, 83, 604;
12. Angew. Chem. Int. Ed. Engl. 1971, 10, 537.
13. M. Kawasaki, T. Ibuki, M. Iwasaki, Y. Takezaki, J. Chem. Phys. 1973, 59, 2076.
14. G. A. Lee, J. Org. Chem. 1976, 41, 2656.
15. R. Huisgen, Angew. Chem. 1977, 89, 589;
16. Angew. Chem. Int. Ed. Engl. 1977, 16, 572.
17. K. Peters, Annu. Rev. Phys. Chem. 1987, 38, 253.
18. L. E. Manring, K. S. Peters, J. Am. Chem. Soc. 1984, 706, 8077.
19. B. E. Arney, Jr., R. C. White, A. Ramanathan, L. Barham, S. Sherrod, P. McCaIl, P. Livanec, K. Mangus, K. White, Photochem. Photobiol. Sci. 2004, 3, 851-853.
20. E. Tapavicza, I. Tavernelli, U. Röthlisberger, C. Filippi, M. E. Casida, J. Chem. Phys. 2008, 129, 124108.
21. CPMD Version 3.13, Copyright IBM Corp 1990-2008, Copyright MPI für Festköperforschung Stuttgart 1997-2001.
22. N. Troullier, J. L. Martins, Phys. Rev. B 1991, 43, 1993.
23. A. D. Becke, Phys. Rev. A 1988, 38, 3098.
24. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
25. I. Frank, J. Hutter, D. Marx, M. Parrinello, J. Chem. Phys. 1998, 108, 4060.
26. S. Grimm, C. Nonnenberg, I. Frank, J. Chem. Phys. 2003, 119, 11574.
27. X Friedrichs, K. Damianos, I. Frank, Chem. Phys. 2008, 347, 17.
28. Gaussian 03, Revision DOl, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, 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, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M, A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
29. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.