Strain Energy of Small Ring Hydrocarbons. Influence of C-H Bond Dissociation Energies

Journal of the American Chemical Society

Volumn 126, Issue 13, 2004, Pages 4444-4452

  Bach, Robert D ^a   Dmitrenko, Olga ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; ENTHALPY; HYDROGENATION; MOLECULAR STRUCTURE; THERMODYNAMIC STABILITY;

ANGULAR RING STRAIN; UNSATURATED HYDROCARBONS;

HYDROCARBONS;

1 METHYLCYCLOPROPENE; ALKENE; CYCLOBUTANE; CYCLOBUTENE; CYCLOPROPANE; CYCLOPROPENE; HYDROCARBON; METHYLCYCLOPROPANE; METHYLENECYCLOPROPANE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; DIMERIZATION; DISSOCIATION; ENERGY; HYDROGENATION; PHYSICAL STRESS; THERMODYNAMICS;

EID: 1842450538     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036309a     Document Type: Article

References (38)

1. For a recent discussion of the basic concepts involved in estimating conventional strain energies see: (a) Alcami, M.; Mo, O.; Yanez, M. J. Compt. Chem. 1998, 19, 1072.
2. (b) Lewis, L. L.; Turner, L. L.; Salter, E. A.; Magers, D. H. J. Mol. Struct.: THEOCHEM 2002, 592, 161 and references therein.
3. (a) Cremer, D.; Kraka, E. In Theoretical Models of the Chemical Bond; Maksic, Z. B., Ed.; Springer: Heidelberg, Germany, 1990; Vol. 2, p 453.
4. (b) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978.
5. (a) Bach, R. D.; Dmitrenko, O. J. Org. Chem. 2002, 67, 2588.
6. (b) Bach, R. D.; Dmitrenko, O. J. Org. Chem. 2002, 67, 3884.
7. (a) Wiberg, K. W. Angew. Chem., Int. Ed. Engl. 1986, 25, 312.
8. (b) Wiberg, K. W.; Fenoglio, R. A. J. Am. Chem. Soc. 1968, 90, 3395.
9. Dudev, T.; Lim, C. J. Am. Chem. Soc. 1998, 120, 4450.
10. Johnson, W. T. G.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 5930.
11. (a) Bader, R. F. W.; Tang, T.-H.; Tal, Y.; Biegler-Konig, F. W. J. Am. Chem. Soc. 1982, 104, 946.
12. (b) Bader, R. F. W. Atoms In Molecules: A Quantum Theory; Oxford University Press: Oxford, 1990.
13. (c) Grimme, S. J. Am. Chem. Soc. 1996, 118, 1529.
14. (d) Exner, K.; Schleyer, P. v R. J. Phys. Chem. A 2001, 105, 3407.
15. (e) Krygowski, T. M.; Ciesielski, A.; Bird, C. W.; Kotschy, A. J. Chem. Inf. Comput. Sci. 1995, 35, 203.
16. (f) Howard, S. T.; Cyranski, M. K.; Stolarczyk, L. Z. J. Chem. Soc., Chem. Commun. 2001, 197.
17. For earlier examples of the use of homodesmotic reactions, see: George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317.
18. (d) George, P.; Trachtman, M.; Brett, A. M.; Bock, C. W. J. Chem. Soc., Perkins Trans. 2 1977, 1036.
19. (a) Cremer, D.; Kraka, E.; Szalay, P. G. Chem. Phys. Lett. 1998, 292, 97.
20. (b) Skancke, A.; Van Vechten, D.; Liebman, J. F.; Skancke, P. N. J. Mol. Struct. 1996, 376, 461 and references therein.
21. (c) Liebman, J. F.; Skancke, P. N. Int. J. Quantum Chem. 1996, 58, 707.
22. (d) Zeiger, D. N.; Liebman, J. F. J. Mol. Struct. 2000, 556, 83.
23. (e) Skancke, A.; Liebman, J. F. J. Org. Chem. 1999, 64, 6361.
24. Bachrach, S. M. J. Chem. Educ. 1990, 67, 907.
25. (a) In general, the G2 BDEs are about 2 kcal/mol higher in energy than the experimental C-H (99.4 ± 0.5 kcal/mol) and C-C (86.2 ± 0.6 kcal/mol) bond dissociation energies for propane.
26. (b) The C-H BDE in cyclopropane at 298 K is reported to be 106.3 ± 0.3 kcal/mol (Baghal-Vayjooee, M. H.; Benson, S. W. J. Am. Chem. Soc. 1979, 101, 2838), while the secondary C-H BDE in propane was measured to be 98. 6 ± 0.4 kcal/mol (Seakins, P. W.; Pilling, M. J.; Niranen, J. T.; Gutman, D.; Kransoperov, L. N. J. Phys. Chem. 1992, 96, 9847).
27. (b) The C-H BDE in cyclopropane at 298 K is reported to be 106.3 ± 0.3 kcal/mol (Baghal-Vayjooee, M. H.; Benson, S. W. J. Am. Chem. Soc. 1979, 101, 2838), while the secondary C-H BDE in propane was measured to be 98. 6 ± 0.4 kcal/mol (Seakins, P. W.; Pilling, M. J.; Niranen, J. T.; Gutman, D.; Kransoperov, L. N. J. Phys. Chem. 1992, 96, 9847).
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; 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. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998. Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 80, 11623.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; 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. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998. Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 80, 11623.
30. (a) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
31. (b) Schlegel, H. B. Adv. Chem. Phys. 1987, 67, 249.
32. (c) Schlegel, H. B. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995; p 459.
33. (a) Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
34. (b) Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
35. (c) Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1996, 104, 2598.
36. (d) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764.
37. (a) Gauss, J.; Cremer, D.; Stanton, J. F. J. Phys. Chem. A 2000, 104, 1319.
38. (b) Barone, V.; Adamo, C.; Brunel, Y.; Subra R. J. Chem. Phys. 1996, 105, 3168.