QTAIM-DI-VISAB computational study on the Diels-Alder reaction of cyclopentadiene - On the nature of the so-called secondary orbital interactions

Canadian Journal of Chemistry

Volumn 86, Issue 7, 2008, Pages 737-744

  Werstiuk, Nick Henry ^a   Sokol, Wojciech ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

Atom energy analysis; Bispericyclic transition states; Bonding; Cyclopentadiene dimerization; DFT calculations; QTAIM DI VISAB analysis

Indexed keywords

ATOMIC PHYSICS; ATOMS; CHEMICAL REACTIONS; CHEMISTRY; CYCLOADDITION; DIMERIZATION; FLOW INTERACTIONS; HYDROGEN; OLEFINS; PHYSICAL CHEMISTRY; REACTION KINETICS; ROCKETS;

BONDING INTERACTIONS; CARBON ATOMS; CHEMICAL PROBLEMS; COMPUTATIONAL STUDIES; CYCLOADDITION REACTIONS; CYCLOPENTADIENE; DASHED LINES; DIELS-ALDER (DA) REACTION; DIFFERENT TYPES; GROUND-STATE MOLECULES; HYDROGEN ATOMS; IN TRANSITIONS; KINETIC PRODUCT; ORBITAL INTERACTIONS; PHYSICAL ORGANIC CHEMISTRY; SOLID LINES; STEREOSELECTIVITIES; TRANSITION STATE (TS);

ADDITION REACTIONS;

EID: 46249127846     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V08-070     Document Type: Article

References (27)

1. (a) K. Alder and G. Stein. Liebigs Ann. Chem. 504, 210 (1933);
2. (b) K. Alder and G. Stein. Angew. Chem. 47, 837 (1934);
3. (c) K. Alder and G. Stein. Angew. Chem. 50, 514 (1937).
4. (a) R. Hoffmann and R.B. Woodward. J. Am. Chem. Soc. 87, 4388 (1965);
5. (b) R. Hoffmann and R.B. Woodward. The conservation of orbital symmetry. Academic Press, New York; 1970;
6. (c) I. Fleming. Frontier orbital and organic chemical reactions. Wiley, New York. 1967;
7. (d) D. Ginsburg. Tetrahedron, 39, 2095 (1983);
8. (d) J.I. Garcia, J.A. Mayoral, and L. Salvatells. Acc. Chem. Res. 33, 658 (2000).
9. P. Caramella, P. Quadrelli, and L. Toma. J. Am. Chem. Soc. 124, 1130 (2002).
10. R.F.W. Bader. Atoms in molecules: A quantum theory. Oxford University Press, Oxford, UK. 1990.
11. T. Bajorek and N. H. Werstiuk. Can. J. Chem. 83, 1352 (2005).
12. D.A. Poulsen and N.H. Werstiuk. J. Chem. Theory. Comput. 2, 77 (2006).
13. N.H. Werstiuk. J. Chem. Theory. Comput. 3, 2258 (2007).
14. E. Brown, R.F.W. Bader, and N.H. Werstiuk. Can. J. Chem. Manuscript in preparation.
15. M.J. Frisch, G.W. Tracks, 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 [computer program]. Revision C.02. Gaussian, Inc., Wallingford CT. 2004.
16. N.H. Werstiuk and H.M. Muchall. J. Mol. Struct. (Theochem.) 463, 225 (1999).
17. N.H. Werstiuk and H.M. Muchall. J. Phys. Chem. A, 103, 6599 (1999).
18. N.H. Werstiuk and H.M. Muchall, J. Phys. Chem. A, 104, 2054 (2000).
19. N.H. Werstiuk, H.M. Muchall, and S.J. Noury. J. Phys. Chem. A, 104, 11601 (2000).
20. C. Adamo and V. Barone. J. Chem. Phys. 108, 664 (1998).
21. ChemCraft [computer program]. Version 1.5. Available from http://www.chemcraftprog.com.
22. R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W.L. Hovell, and R. Gilliland. GaussView [computer program]. Version 3.09. Semichem, Inc., Shawnee Mission, Kans. 2003.
23. F. Biegler-Konig. AIM 2000 [computer program]. University of Applied Science, Bielefeld, Germany. 1998-2000.
24. Y-G. Wang and N.H. Werstiuk. J. Comput. Chem. 24, 379 (2003).
25. Y-G. Wang, C. Matta, and N.H. Werstiuk. J. Comput. Chem. 24, 1720 (2003).
26. Y-G. Wang, K.B. Wiberg, and N.H. Werstiuk. J. Phys. Chem. A, 111, 3592 (2007).
27. T.A. Keith. AIMALL97 Package (B3) for WINDOWS [computer program]. Available from aim@tkgristmill.com.