Ring strain energies: Substituted rings, norbornanes, norbornenes and norbornadienes

Tetrahedron

Volumn 60, Issue 37, 2004, Pages 8103-8112

  Khoury, Peter R ^a   Goddard, John D ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Norbornadienes; Norbornanes; Norbornenes; Ring strain; Substituents

Indexed keywords

FUNCTIONAL GROUP; NORBORNADIENE DERIVATIVE; NORBORNANE DERIVATIVE; NORBORNENE DERIVATIVE;

ARTICLE; CHEMICAL BOND; ENERGY; EVALUATION; PREDICTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; THEORY;

EID: 4143145258     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.100     Document Type: Article

References (30)

1. P.v.R Schleyer, J.E. Williams, and K.R. Blanchard J. Am. Chem. Soc. 92 1970 8
2. S.W. Benson, F.R. Cruickshank, D.M. Golden, G.R. Haugen, H.E. O'Neal, A.S. Rodgers, R. Shaw, and R. Walsh Chem. Rev. 69 1969 251
3. P. George, M. Trachman, C.W. Bock, and A.M. Brett Tetrahedron 32 1976 317
4. K. Wiberg J. Comp. Chem. 5 1983 2
5. T. Dudev, and C. Lim J. Am. Chem. Soc. 120 1998 4450
6. R. Bach, and O. Dimitrenko J. Org. Chem. 67 2002 2588
7. C. Delamare, C. Jakins, and E. Lewars Can. J. Chem. 79 2001 1492
8. J.D. Dill, A. Greenberg, and J.F. Liebman J. Am. Chem. Soc. 101 1979 6814
9. I. Novak J. Org. Chem. 67 2002 6279
10. I. Novak Chem. Phys. Lett. 380 2003 258
11. P. Mayo, and W. Tam Tetrahedron 58 2002 9513
12. P. Mayo, and W. Tam Tetrahedron 58 2002 9527
13. K.B. Wiberg, R.F.W. Bader, and C.D.H. Lau J. Am. Chem. Soc. 109 1987 1001
14. These values may be estimated using: r=1.748-0.002371(BDE) and the B3LYP bond lengths. see: A. Zavistas J. Phys. Chem. A 107 2003 897
15. J.D. Cox, and G. Pilcher Thermochemistry of Organic Compounds 1970 Academic London pp 553-559
16. L.A. Curtiss, R. Krishnan, P.C. Redfern, and J.A. Pople J. Chem. Phys. 112 2000 7374
17. L.A. Curtiss, R. Krishnan, P.C. Redfern, and J.A. Pople J. Chem. Phys. 106 1997 1063
18. 2=76.0 kcal/mol and of Et-Et=87.2 kcal/mol are predicted using the bond length-bond energy equation from Ref. 14
19. Unlike the other branched alkanes, isobutane and neopentane are predicted to be stabilized relative to their acyclic isomers at the B3LYP level of theory. The tertiary and quaternary energy corrections are included in the reference energy so as to cancel the stabilization energy in the ring due to tertiary and quaternary carbons
20. K. Wiberg Angew. Chem., Int. Ed. Engl. 25 1986 312
21. th ed. 1992 Wiley Interscience New York p 153
22. R.W. Jordan, and W. Tam Org. Lett. 3 2001 2367
23. G. Maier Angew. Chem., Int. Ed. Engl. 1998 309
24. R.W. Jordan, and W. Tam Tetrahedron Lett. 43 2002 6051
25. P.H. Mazzocchi, J.D. Stahly, N.G. Rondan, L.N. Domelsmith, M.D. Rozeboom, P. Caramella, and K.N. Houk J. Am. Chem. Soc. 102 1980 6482
26. R.W. Jordan, and W. Tam Org. Lett. 2 2000 3031
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian98; Gaussian, Inc., Pittsburgh PA, 1998.
28. A.D. Becke J. Chem. Phys. 98 1993 5648
29. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
30. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623