An ab initio study of 1,5-suprafacial shifts in 5-substituted 1,3-cyclopentadienes

Canadian Journal of Chemistry

Volumn 83, Issue 9, 2005, Pages 1299-1305

  Pye, Cory C ^a   Poirier, Raymond A ^b  

^a SAINT MARY S UNIVERSITY   (Canada)

^b MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

1,2 haptotropic shift; 1,5 suprafacial shift; 5 substituted 1,3 cyclopentadiene; Ab initio; Transition states

Indexed keywords

CARBON; COMPUTATIONAL METHODS; GEOMETRY; HYDROGEN; REACTION KINETICS; SUBSTITUTION REACTIONS;

1,2-HAPTOTROPIC SHIFT; 1,5-SUPRAFACIAL SHIFT; 5-SUBSTITUTED 1,3-CYCLOPENTADIENE; AB INITIO; TRANSITION STATES;

NITROGEN COMPOUNDS;

1,3 CYCLOPENTADIENE DERIVATIVE; CARBON; CYCLOPENTADIENE DERIVATIVE; HYDROGEN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BINDING; CORRELATION ANALYSIS; GEOMETRY; PHASE TRANSITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 33644584202     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-141     Document Type: Article

References (38)

1. C.C. Pye, J.D. Xidos, D.J. Burnell, and R.A. Poirier. Can. J. Chem. 81, 14 (2003).
2. W.R. Roth. Tetrahedron Lett. 1009 (1964).
3. J.W. De Haan and H. Kloosterziel. Reel. Trav. Chim. Pays-Bas, 87, 298 (1968).
4. A. Bonny and S.R. Stobart. J. Chem. Soc. Dalton Trans. 224 (1980).
5. N.M. Sergeyev, G.I. Avramenko, A.V. Kisin, V.A. Korenevsky, and Yu.A. Ustynyuk. J. Organomet. Chem. 32, 55 (1971).
6. A.V. Kisin, V.A. Korenevsky, N.M. Sergeyev, and Yu.A. Ustynyuk. J. Organomet. Chem. 34, 93 (1972).
7. P. Jutzi and H. Saleske. Chem. Ber. 117, 222 (1984).
8. R.B. Larrabee. J. Organomet. Chem. 74, 313 (1974).
9. P. Jutzi and G. Reumann. J. Chem. Soc. Dalton Trans. 2237 (2000).
10. P.H. Budzelaar, J.J. Engelberts, and J.H. van Lenthe. Organometallics, 22, 1662 (2003).
11. R.A. Poirier, M.R. Peterson, and A. Yadav. MUNGAUSS [computer program]. Chemistry Department, Memorial University of Newfoundland, St. John's, Newfoundland. 1990.
12. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.W. Wong, J.B. Foresman, M.A. Robb, M. Head-Gordon, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, and J.A. Pople. 1993. GAUSSIAN 92/DFT. Revision F.4 [computer program]. Gaussian, Inc., Pittsburgh, Penn. 1993.
13. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., 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. Peterson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Ciolowski, J.V. Ortiz, A.G. Baboul, 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, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople. GAUSSIAN 98. Revision A.9 [computer program]. Gaussian, Inc., Pittsburgh, Penn. 1998.
14. H, Li-F.: W.J. Hehre, R.F. Stewart, and J.A. Pople. J. Chem. Phys. 51, 2657 (1969).
15. He, Ne, Na-Ar: W.J. Hehre, R. Ditchfield, R.F. Stewart, and J.A. Pople. J. Chem. Phys. 52, 2769 (1980).
16. K, Ca, Ga-Kr: W.J. Pietro, B.A. Levi, W.J. Hehre, and R.F. Stewart. Inorg. Chem. 19, 2225 (1980)
17. Rb, Se, In-Xe: W.J. Pietro, E.S. Blurock, R.F. Hout, W.J. Hehre, D.J. Defrees, and R.F. Stewart. Inorg. Chem. 20, 3650 (1981).
18. H-Ne: J.S. Binkley, J.A. Pople, and W.J. Hehre. J. Am. Chem. Soc. 102, 939 (1980).
19. Na-Ar: M.S. Gordon, J.S. Binkley, J.A. Pople, W.J. Pietro, and W.J. Hehre. J. Am. Chem. Soc. 104, 2797 (1982).
20. K, Ca, Ga-Kr, Rb, Sr, In-Xe: K.D. Dobbs and W.J. Hehre. J. Comput. Chem. 7, 359 (1986).
21. C-F 6-31G: W.J. Hehre, R. Ditchfield, and J.A. Pople. J. Chem. Phys. 56, 2257 (1972).
22. H, C-F polarization functions: P.C. Hariharan and J.A. Pople. Theor. Chim. Acta, 28, 213 (1973).
23. Na-Ar: M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. Defrees, and J.A. Pople. J. Chem. Phys. 77, 3654 (1982).
24. H, Li-F diffuse: T. Clark, J. Chandrasekhar, G.W. Spitznagel, and P.v.R. Schleyer. J. Comput. Chem. 4, 294 (1983).
25. S. Huzinaga, J. Andzelm, M. Klobutowski, E. Radio-Andzelm, Y. Sakei, and H. Tatewaki. Gaussian basis sets for molecular calculations. ELsevier Science Publishers, Amsterdam. 1984.
26. C.C. Pye. Ph.D. thesis, Memorial University, St. John's, New-foundland. 1997. Chapter 3, section 2 (pp. 78-91) of this thesis contains a discussion of the STO-3G, 3-2IG, and 6-31G(d) Hartree-Fock calculations.
27. A. Szabo and N.S. Ostlund. Modern quantum chemistry: Introduction to advanced electronic structure theory. 1st ed. (revised). McGraw-Hill, New York. 1989, and refs. therein.
28. G. Schaftenaar and J.H. Noordik. J. Comput.-Aided Mol. Des. 14, 123 (2000).
29. N.G. Rondan and K.N. Houk. Tetrahedron Lett. 25, 2519 (1984).
30. S.M. Bachrach. J. Org. Chem. 58, 5414 (1993).
31. H. Jiao and P.v.R. Schleyer. J. Chem. Soc. Faraday Trans. 90, 1559 (1994).
32. I. Alkorta and J. Elguero. J. Chem. Soc. Perkin Trans. 2, 2497 (1998).
33. B.A. Hess, Jr. and I.E. Baldwin. J. Org. Chem. 67, 6025 (2002).
34. M.J.S. Dewar. Chem. Br. 11, 97 (1975).
35. A.F. Cuthbertson and C. Glidewell. J. Organomet. Chem. 221, 19 (1981).
36. W.W. Schoeller. Z. Naturforsch. B, 38, 1635 (1983).
37. W.W. Schoeller. Z. Naturforsch. B, 39, 1767 (1984).
38. S. El Chaouch, J.-C. Guillemin, T. Karpati, and T. Veszpremi. Organometallics, 20, 5405 (2001).