G2 ab initio calculations of enthalpies of hydrogénation, isomerization, and formation of c3 cyclic and acyclic ketones and alcohols

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7319-7321

  Rogers, Donald W ^a   McLafterty, Frank J ^a   Podosenin, Andrew V ^a  

^a LONG ISLAND UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0442284388     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980820i     Document Type: Article

References (21)

1. Davis, H. E.; Allinger, N. L.; Rogers, D. W. J. Org. Chem. 1985, 50, 3601.
2. Grabowski, J. J.; Simon, J. D.; Peters, K. S. J. Am. Chem. Soc. 1984, 106, 4615.
3. Greenberg, A. A.; Tompkins, R. P. T.; Dobrovolny, M.; Liebman, J. F. J. Am. Chem. Soc. 1983, 705, 6855.
4. Manatt, S. L.; Roberts, J. D. J. Org. Chem. 1959, 24, 1336.
5. (a) Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622.
6. (b) Curtiss, L. A.; Raghavachari, K; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
7. Curtiss, L. A.; Carpenter, J. E.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1992, 96, 9030.
8. (a) Curtiss, L. A.; Redfern, P. C.; Smith, B. J.; Radom, L. J. Chem. Phys. 1996, 104, 5148.
9. (b) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
10. Raghavachari, K.; Stefanov, B. B.; Curtiss, L. A. J. Chem. Phys. 1997,106, 6764.
11. (a) Rogers, D. W.; McLafferty, F. J. J. Phys. Chem. 1995, 99, 1375.
12. (b) Rogers, D. W.; McLafferty, F. J.; Podosenin, A. V. J. Phys. Chem. 1996,100,17148.
13. Rogers, D. W.; McLafferty, F. J.; Podosenin, A. V. J. Phys. Chem. 1997, 101, 4776.
14. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheesman, J. R.; Kieth, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, G.; Pople, J. A. Gaussian 94, revision C.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
15. In the determination of ACP of the hydrogénation of cyclopropenone to cyclopropanone for example, Cp of the ketones nearly cancel, leaving hydrogen as the only contributor to ACP. See refs 8b,c.for details.
16. Wiberg, K. B.; Crocker, L. S.; Morgan, K. M. J. Am. Chem. Soc. 1991, 113, 3447.
17. (a) Rodrigues, H. J.; Chang, J.-C.; Thomas, T. F. J. Am. Chem. Soc. 1976,98,2027.
18. (b) Liebman, J. F.; Greenberg, A. Chem. Rev. 1989, 89,1225.
19. Slayden, S. W.; Liebman, J. F. In The Chemistry of Doublebonded Functional Groups; Patai, S., Ed.; John Wiley and Sons: New York, 1997; Supplement A3, Chapter 11.
20. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986.
21. Stewart, J. J. S. J. Comput.-Aided Mol. Des. 1990, 4, 1 and references therein.