Ab initio characterization of ring-opening H-transfer in ionized cyclopentanone: Similarity to ion-neutral complex-mediated alkane eliminations

Journal of the American Society for Mass Spectrometry

Volumn 7, Issue 12, 1996, Pages 1251-1254

  Hudson, Charles E ^a   McAdoo, David J ^a  

^a UNIVERSITY OF TEXAS MEDICAL BRANCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CYCLOPENTANONE DERIVATIVE; ION; PROTON;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENERGY TRANSFER; MOLECULAR INTERACTION; PROTON TRANSPORT;

EID: 0030560724     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1044-0305(96)00103-1     Document Type: Article

References (20)

1. 1. Hammerum, S.; Donchi, K. F.; Derrick, P. J. Int. J. Mass Spectrom. Ion Phys. 1983, 47, 347.
2. 2. (a) Wendelboe, J. F.; Bowen, R. D.; Williams, D. H. J. Am. Chem. Soc. 1981, 103, 2334;
3. (b) Hudson, C. E.; McAdoo, D. J. Int. J. Mass Spectrom. Ion Processes 1984, 59, 325;
4. (c) Hammerum, S.; Audier, H. E. J. Chem. Soc. Chem. Commun. 1988, 860;
5. (d) Heinrich, N.; Louage, F.; Lifshitz, C.; Schwarz, H. J. Am. Chem. Soc. 1988, 110, 8183;
6. (e) McAdoo, D. J.; Traeger, J. C.; Hudson, C. E.; Griffin, L. L. J. Phys. Chem. 1988, 92, 1524;
7. (f) Traeger, J. C.; Hudson, C. E.; McAdoo, D. J. J. Phys. Chem. 1988, 92, 1519;
8. (g) Olivella, S.; Sole, A.; McAdoo, D. J.; Griffin, L. L. J. Am. Chem. Soc. 1994, 116, 11078;
9. (h) Olivella, S.; Sole, A.; McAdoo, D. J.; Griffin, L. L. J. Am. Chem. Soc. 117, 2557;
10. (i) Traeger, J. C.; Hudson, C. E.; McAdoo, D. J. J. Am. Soc. Mass Spectrom. 1996, 7, 73.
11. 3. Budzikiewicz, H.; Djerassi, C.; Williams, D. H. Mass Spectrometry of Organic Compounds; Holden-Day: San Francisco, 1967; pp 107, 143.
12. 4. Longevialle, P.; Lefèvre, O. Org. Mass Spectrom. 1993, 28, 1083.
13. 5. McAdoo, D. J.; Hudson, C. E. Int. J. Mass Spectrom. Ion Processes 1984, 62, 269.
14. 6. McAdoo, D. J.; McLafferty, F. W.; Parks, T. E. J. Am. Chem. Soc. 1972, 94, 1601.
15. 7. Hudson, C. E.; McAdoo, D. J. Org. Mass Spectrom. 1984, 19, 1.
16. 8. Smith, R. L.; Chyall, L. J.; Chou, P. K.; Kenttämaa, H. I. J. Am. Chem. Soc. 1994, 116, 781.
17. 9. Streitwieser, A., Jr. Solvolytic Displacement Reactions; McGraw-Hill: New York, 1962; p 105.
18. 10. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, 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, C.; Pople, J. A. Gaussian 94, Revision B.; Gaussian, Inc.: Pittsburgh, PA, 1995.
19. 11. Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 209.
20. 12. McAdoo, D. J.; Morton, T. H. Acc. Chem. Res. 1993, 26, 295.