Nature of the ring-closure process along the rearrangement of octa-1,3,5,7-tetraene to cycloocta-1,3,5-triene from the perspective of the electron localization function and catastrophe theory

Journal of Computational Chemistry

Volumn 33, Issue 7, 2012, Pages 748-756

  Andres J ^a   Berski, S ^b   Domingo, L R ^c   Gonzalez Navarrete P ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF WROC AW   (Poland)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

catastrophe theory; chemical bond; cyclooctatriene; electrocyclic reactions; electron localization function; octatetraene; ring closure process

Indexed keywords

CATASTROPHE THEORY; CYCLOOCTATRIENE; ELECTROCYCLIC REACTIONS; ELECTRON LOCALIZATION FUNCTION; OCTATETRAENE; RING-CLOSURE PROCESS;

CHEMICAL BONDS; DISASTERS; STABILITY; SYSTEM THEORY; TOPOLOGY;

ELECTRONS;

EID: 84857116614     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.22898     Document Type: Review

References (47)

1. E. Kraka, D. Cremer, Acc Chem Res 2010, 43, 591.
2. P. Hohenberg, W. Kohn, Phys Rev B 1964, 136, B864.
3. R. F. W. Bader, Atoms in Molecules: A Quantum Theory; Clarendon Press Oxford New York, 1990.
4. C. R. F. Matta, R. J. Boyd, The Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design; Wiley-VCH: Weinheim, 2007.
5. P. L. A. Popelier, Atoms in Molecules: An Introduction; Prentice Hall: Harlow, 2000.
6. R. F. W. Bader, Theor Chem Acc 2001, 105, 276.
7. P. L. A. Popelier, Coord Chem Rev 2000, 197, 169.
8. F. Corts-Guzman, R. F. W. Bader, Coord Chem Rev 2005, 249, 633.
9. G. Merino, A. Vela, T. Heine, Chem Rev 2005, 105, 3812.
10. D. Stalke, ChemâEur J 2011, 17, 9264.
11. A. D. Becke, K. E. Edgecombe, J Chem Phys 1990, 92, 5397.
12. B. Silvi, A. Savin, Nature 1994, 371, 683.
13. A. Savin, B. Silvi, F. Colonna, Can J Chem 1996, 74, 1088.
14. T. Burnus, M. A. L. Marques, E. K. U. Gross, Phys Rev A 2005, 71, 010501.
15. E. Rasanen, A. Castro, E. K. U. Gross, Phys Rev B 2008, 77, 115108.
16. Y. Tal, R. F. W. Bader, T. T. Nguyendang, M. Ojha, S. G. Anderson, J Chem Phys 1981, 74, 5162.
17. N. O. J. Malcolm, P. L. A. Popelier, J Phys Chem A 2001, 105, 7638.
18. X. Krokidis, S. Noury, B. Silvi, J Phys Chem A 1997, 101, 7277.
19. M. Merli, F. Nestola, L. Sciascia, Eur J Mineral 2011, 23, 197.
20. S. Berski, F. R. Sensato, V. Polo, J. Andres, V. S. Safont, J Phys Chem A 2011, 115, 514.
21. V. Polo, J. Andres, J Chem Theor Comp 2007, 3, 816.
22. V. Polo, J. Andres, S. Berskit, L. R. Domingo, B. Silvi, J Phys Chem A 2008, 112, 7128.
23. V. Polo, P. Gonzalez-Navarrete, B. Silvi, J. Andres, Theor Chem Acc 2008, 120, 341.
24. V. Polo, J. Andres, R. Castillo, S. Berski, B. Silvi, ChemâEur J 2004, 10, 5165.
25. J. Andres, S. Berski, L. R. Domingo, V. Polo, B. Silvi, Curr Org Chem 2011, 15, 3566.
26. J. Poater, M. Sola, F. M. Bickelhaupt, ChemâEur J 2006, 12, 2902.
27. S. G. Wang, Y. X. Qiu, W. H. E. Schwarz, ChemâEur J 2010, 16, 9107.
28. R. F. W. Bader, T. T. Nguyendang, Y. Tal, J Chem Phys 1979, 70, 4316.
29. Y. Tal, R. F. W. Bader, J. Erkku, Phys Rev A 1980, 21, 1.
30. R. Thom, Structural Stability and Morphogenesis; An Outline of a General Theory of Models; W. A. Benjamin: Reading, Mass., 1975.
31. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim/Bergstr, 1970.
32. B. E. Thomas, J. D. Evanseck, K. N. Houk, J Am Chem Soc 1993, 115, 4165.
33. B. Lecea, A. Arrieta, F. P. Cossio, J Org Chem 2005, 70, 1035.
34. 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, and, J. A. Pople, Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004.
35. K. Fukui, Acc Chem Res 1981, 14, 363.
36. M. Kohout, Dgrid, Version 4.5, Radebeul, 2009.
37. G. Schaftenaar, J. H. Noordik, J Comput Aided Mol Des 2000, 14, 123.
38. W. Humphrey, A. Dalke, K. Schulten, J Mol Graphics 1996, 14, 33.
39. S. Noury, X. Krokidis, F. Fuster, B. Silvi, Comput Chem 1999, 23, 597.
40. S. Berski, J. Andres, B. Silvi, L. R. Domingo, J Phys Chem A 2006, 110, 13939.
41. B. Silvi, I. Fourre, M. E. Alikhani, Monatsh Chem 2005, 136, 855.
42. S. Berski, J. Andres, B. Silvi, L. R. Domingo, J Phys Chem A 2003, 107, 6014.
43. V. Polo, J. Andres, J Comp Chem 2005, 26, 1427.
44. L. R. Domingo, E. Chamorro, P. Perez, Org Biomol Chem 2010, 8, 5495.
45. I. M. Ndassa, B. Silvi, F. Volatron, J Phys Chem A 2010, 114, 12900.
46. J. C. Santos, J. Andres, A. Aizman, P. Fuentealba, V. Polo, J Phys Chem A 2005, 109, 3687.
47. J. C. Santos, V. Polo, J. Andres, Chem Phys Lett 2005, 406, 393.