Azulene-to-naphthalene rearrangement: The Car-Parrinello metadynamics method explores various reaction mechanisms

ChemPhysChem

Volumn 5, Issue 10, 2004, Pages 1558-1568

  Stirling, András ^a   Iannuzzi, Marcella ^a   Laio, Alessandro ^a   Parrinello, Michele ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Ab initio calculations; Azulene; Metadynamics; Molecular dynamics; Reaction mechanisms

Indexed keywords

ACTIVATION ENERGY; CALCULATIONS; MOLECULAR DYNAMICS; NAPHTHALENE;

AB INITIO CALCULATIONS; AZULENES; CAR-PARRINELLO MOLECULAR-DYNAMICS; ELEMENTARY STEPS; HIGH ACTIVATION ENERGY; INTRAMOLECULAR MECHANISM; METADYNAMICS; REACTION MECHANISM;

REACTION KINETICS;

AZULENE; NAPHTHALENE;

ARTICLE; CAR PARRINELLO METADYNAMICS; CHEMICAL REACTION; ENERGY; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; REACTION ANALYSIS; SIMULATION;

EID: 8144220821     PISSN: 14394235     EISSN: None     Source Type: Journal    
DOI: 10.1002/cphc.200400063     Document Type: Article

References (50)

1. E. Heilbronner, K. Wieland, Helv. Chim. Acta 1947, 30, 947.
2. L. T. Scott, G. K. Agopian, J. Am. Chem. Soc. 1977, 99, 4506.
3. R. W. Alder, G. Whittaker, J. Chem. Soc. Perkin Trans. 2 1975, 714.
4. R. W. Alder, C. Wilshire, J. Chem. Soc. Perkin Trans. 2 1975, 1464.
5. R. W. Alder, R. W. Whiteside, G. Whittaker, C. Wilshire, J. Am. Chem. Soc. 1979, 107, 629.
6. J. Becker, C. Wentrup, E. Katz, K.-P. Zeller, J. Am. Chem. Soc. 1980, 102, 5112.
7. L. T. Scott, M. A. Kirms, J. Am. Chem. Soc. 1981, 103, 5875.
8. H. Gugel, K.-P. Zeller, C. Wentrup, Chem. Ber. 1983, 116, 2775.
9. L. T. Scott, M. A. Kirms, B. L. Earl, J. Chem. Soc., Chem. Commun. 1983, 1373.
10. A. Wetzel, K.-P. Zeller, Z. Naturforsch. B 1987, 42, 903.
11. L. Brouwer, J. Troe, Int. J. Chem. Kin. 1988, 20, 379.
12. A. Laskin, A. Lifshitz, Isr. J. Chem. 1996, 36, 257.
13. F. Keller, H.-D. Beckhaus, C. Ruchardt, Liebigs Ann. Recueil 1997, 2055.
14. L. T. Scott, Acc. Chem. Res. 1982, 15, 52.
15. L. T. Scott, J. Org. Chem. 1984, 49, 3021.
16. H. J. Kallen, Ph.D. Thesis, ETH, Zürich 1958.
17. M. J. S. Dewar, K. M. Merz, J. Am. Chem. Soc. 1985, 107, 6111.
18. M. J. S. Dewar, K. M. Merz, J. Am. Chem. Soc. 1986, 108, 5142.
19. M. J. S. Dewar, K. M. Merz, J. Am. Chem. Soc. 1986, 108, 5146.
20. R. W. Alder, S. P. East, J. N. Harvey, M. T. Oakley, J. Am. Chem. Soc. 2003, 125, 5375.
21. C. J. Cerjan, W. H. Miller, J. Chem. Phys. 1981, 75, 2800.
22. K. J. Laidler, C. King, J. Phys. Chem. 1983, 87, 2657.
23. K. Fukui, Acc. Chem. Res. 1981, 14, 363.
24. E. A. Carter, G. Ciccotti, J. T. Hynes, R. Kapral, Chem. Phys. Lett. 1989, 156, 472.
25. M. Sprik, G. Ciccotti, J. Chem. Phys. 1998, 109, 7737.
26. G. Mills, H. Jónsson, G. K. Schenter, Surf. Sci. 1995, 324, 305.
27. G. M. Torrie, J. P. Valleau, J. Chem. Phys. 1977, 66, 1402.
28. J. VandeVondele, U. Rothlisberger, J. Chem. Phys. 2000, 113, 4863.
29. J. A. Rahman, J. C. Tully, J. Chem. Phys. 2002, 116, 8750.
30. J. VandeVondele, U. Rothlisberger, J. Am. Chem. Soc. 2002, 124, 8163.
31. D. Passerone, M. Parrinello, Phys. Rev. Lett. 2001, 87, 108302.
32. P. G. Bolhuis, D. Chandler, C. Dellago, P. L. Geissler, Annu. Rev. Phys. Chem. 2002, 53, 291.
33. M. Iannuzzi, A. Laio, M. Parrinello, Phys. Rev. Lett. 2003, 90, 238302.
34. A. Laio, M. Parrinello, Proc. Natl. Acad. Sci. USA 2002, 99, 12562.
35. C. Micheletti, A. Laio, M. Parrinello, Phys. Rev. Lett. 2004, 92, 170601.
36. R. Car, M. Parrinello, Phys. Rev. Lett. 1985, 55, 2471.
37. CPMD V3.7 Copyright IBM Corp 1990-2001, Copyright MPI für Festkörperforschung Stuttgart 1997-2001.
38. a) A. Becke, Phys. Rev. A 1988, 38, 3098;
39. b) C. Lee, W. Yang, R. Parr, Phys. Rev. B 1988, 37, 785.
40. N. Troullier, J. L. Martins, Phys. Rev. B 1991, 43, 1993.
41. W. H. Press, A. A. Teukolsky, W. T. Vetterling, B. P. Flannery, Numerical Recipes, Cambridge University Press, Cambridge, 1992.
42. Gaussian 98 (Revision A.11), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
43. O. Wiest, D. C. Montiel, K. N. Houk, J. Phys. Chem. A 1997, 101, 8378.
44. M. Sprik, Faraday Discuss. 1998, 110, 437.
45. C. Salter, J. B. Foresman, J. Chem. Educ. 1998, 10, 1341.
46. S. C. Ammal, H. Yamataka, M. Aida, M. Dupuis, Science 2003, 299, 1555.
47. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
48. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
49. U. Burger, P. J. Thorel, Y. Mentha, Chimia 1987, 41, 26.
50. T. J. Katz, R. J. Roth, N. Acton, E. J. Carnahan, J. Org. Chem. 1999, 64, 7663.