C-H bond dissociation energies of alkyl amines: Radical structures and stabilization energies

Journal of the American Chemical Society

Volumn 119, Issue 38, 1997, Pages 8925-8932

  Wayner, D D M ^a   Clark, K B ^a   Rauk, A ^b   Yu, D ^b   Armstrong, D A ^b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; AMINE; DIMETHYLAMINE; ETHYLAMINE; METHYLAMINE; MORPHOLINE; PIPERAZINE; PIPERIDINE; PYRROLIDINE DERIVATIVE; RADICAL; TRIETHYLAMINE; TRIMETHYLAMINE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; DISSOCIATION; ELECTRON TRANSPORT; ENERGY; MOLECULAR STABILITY;

EID: 0030747120     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971365v     Document Type: Article

References (28)

1. Dewar, M. J. S.; Fox, M. A.; Nelson, D. J. J. Organomet. Chem. 1980, 185, 157.
2. T may be used.
3. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
4. Armstrong, D. A.; Rauk, A.; Yu, D. J. Am. Chem. Soc. 1993, 115, 666.
5. (a) Griller, D.; Lossing, F. P. J. Am. Chem. Soc. 1981, 103, 1586.
6. (b) Burkey, T. J.; Castelhano, A. L.; Griller, D.; Lossing, F. P. J. Am. Chem. Soc. 1983, 105, 4701.
7. Goddard, J. D. Can. J. Chem. 1982, 60, 1250.
8. Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062.
9. Lehd, M.; Jensen, F. J. Org. Chem. 1991, 56, 884.
10. Leroy, G.; Sana, M.; Wilante, C. J. Mol. Struct. (Theochem.) 1991, 228, 37.
11. Lein, M. H.; Hopkinson, A. C. J. Comput. Chem. 1985, 6, 274.
12. -1 from ref 3.
13. Merenyi, G.; Lind, J. To be published.
14. Das, S.; Von Sonntag, C. Z. Naturforsch. 1986, 41b, 505.
15. Wayner, D. D. M.; Lusztyk, E.; Page, D.; Ingold, K. U.; Mulder, P.; Laarhoven L. J. J.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, 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, C.; Pople, J. A. Gaussian 94, (SGI-Revision B.3); Gaussian, Inc.: Pittsburgh, PA, 1995.
17. Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1993, 98, 1293.
18. Armstrong, D. A.; Yu, D.; Rauk, A. Can. J. Chem. 1996, 74, 1192.
19. Pople, J. A.; Schlegel, H. B.; Krishnan, R.; Defrees, D. J.; Binkley, J. B.; Frisch, M. J.; Whiteside, R. A.; Hout, R. F.; Hehre, W. J. Int. J. Quantum Chem. Symp. 1981, 15, 269.
20. McQuarrie, D. A. Statistical thermodynamics; Harper & Row: 1973.
21. Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
22. Dobe, S.; Berces, T.; Turanyi, T.; Marta, F.; Grussdorf, J.; Temps, F.; Wagner, H. Gg. J. Phys. Chem. 1996, 100, 19864.
23. Johnson, R. D. III; Hudgens, J. W. J. Phys. Chem. 1996, 100, 19874.
24. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R. H.; Halow, I.; Bailey, S. M.; Churney, K. L.; Nuttal, R. L. J. Phys. Chem. Ref. Data 1982, 11, Suppl. No. 2.
25. Clark, K. B.; Wayner, D. D. M.; Demirdji, S. H.; Koch, T. H. J. Am. Chem. Soc. 1993, 115, 2447.
26. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas Phase Ion and Neutral Thermochemistry. J. Phys. Chem. Ref. Data 1988, 17, Suppl. No. 1.
27. Stein, S. E.; Lias, S. G.; Liebman, J. F.; Levin, R. D.; Kafafi, S. A. NIST Standard Reference Data Base 25, NIST Structures and Properties Version 2.0; U.S. Department of Commerce Gaithersburg, MD, 1994.
28. Another point is that thermal and ZPE differences were neglected in some of the earlier calculations, and this would contribute to differences from the present values.