The water elimination from the ethyl acetate radical cation - Answers from theory to a longstanding mechanistic problem

Canadian Journal of Chemistry

Volumn 83, Issue 11, 2005, Pages 1847-1863

  Lee, Richard ^a   Ruttink, Paul J A ^b   Burgers, Peter C ^c   Terlouw, Johan K ^a  

^a MCMASTER UNIVERSITY   (Canada)

^b UTRECHT UNIVERSITY   (Netherlands)

^c ERASMUS MEDICAL CENTER   (Netherlands)

Author keywords

CBS QB3 model chemistry; Hydroxycarbene shift; Reaction mechanism; Tandem mass spectrometry

Indexed keywords

CHEMICAL BONDS; DISSOCIATION; IONIZATION; ISOMERIZATION; REACTION KINETICS; WATER;

CBS-QB3 MODEL CHEMISTRY; HYDROXYCARBENE SHIFT; TANDEM MASS SPECTROMETRY;

POSITIVE IONS;

2 BUTANONE; 4 HYDROXY 2 BUTANONE; ACETIC ACID ETHYL ESTER; CATION; HYDROGEN; KETONE DERIVATIVE; METHYLVINYL KETONE; OXYGEN; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL MODEL; ISOMERIZATION; REACTION ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 33745220303     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-199     Document Type: Article

References (47)

1. E.W. Godbole and P. Kebarle. Trans. Faraday Soc. 58, 1897 (1962).
2. F.M. Benoit, A.G. Harrison, and F.P. Lossing. Org. Mass Spectrom. 12, 78 (1977).
3. C.G. de Koster, J.K. Terlouw, K. Levsen, H. Halim, and H. Schwarz. Int. J. Mass Spectrom. Ion Processes, 61, 87 (1984).
4. J.L. Holmes and F.P. Lossing. J. Am. Chem. Soc. 102, 1591 (1980).
5. F.W. McLafferty and F. Turecek. Interpretation of mass spectra. 4th ed. University Science Books, Mill Valley, California. 1993. p. 81.
6. A.N.H. Yeo. J. Chem. Soc. Chem. Commun. 1154 (1970).
7. J.L. Holmes, P.C. Burgers, and J.K. Terlouw. Can. J. Chem. 59, 1805 (1981).
8. L. Fraser-Monteiro, M.L. Fraser-Monteiro, J. Butler, and T. Baer. J. Phys. Chem. 86, 752 (1982).
9. (a) J.L. Holmes and J.K. Terlouw. Org. Mass. Spectrom. 15, 383 (1980);
10. (b) J.L. Holmes In Encyclopedia of mass spectrometry. Vol. 1. Edited by P.B. Armentrout. Elsevier, Amsterdam. 2004. p. 91.
11. (a) S. Hammerum. Mass Spectrom. Rev. 7, 123 (1988);
12. (b) P.C. Burgers and J.K. Terlouw. In Specialist periodical reports: mass spectrometry. Vol. 10. Edited by M.E. Rose. The Royal Society of Chemistry, London. 1989. Chap. 2.
13. J.L. Holmes and J.K. Terlouw. In Encyclopedia of mass spectrometry. Vol. 4. Edited by N.M.M. Nibbering. Elsevier, Amsterdam. 2005. p. 287.
14. (a) S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.O. Levin, and W.G. Maillard. J. Phys. Chem. Ref. Data, 17(Suppl. 1). 1988;
15. (b) W.G. Mallard (Editor). NIST Chemistry WebBook [online]. The National Institute of Standards and Technology, Gaithersburg, Maryland. Available from http://webbook.nist. gov/chemistry [accessed April 2005]. 2003;
16. (c) E.P.L. Hunter and S.G. Lias. J. Phys. Chem. Ref. Data, 27, 413 (1998);
17. (d) Y.-R. Luo. Handbook of dissociation energies in organic compounds. CRC Press, Boca Raton, Florida. 2003;
18. (e) N. Cohen and S.W. Benson. Chem. Rev. 93, 2419 (1993).
19. (a) J.K. Terlouw, W. Heerma, J.L. Holmes, and P.C. Burgers. Org. Mass. Spectrom. 15, 582 (1980);
20. (b) C. Dass and M.L. Gross. Org. Mass. Spectrom. 25, 24 (1990).
21. N. Heinrich, J. Schmidt, H. Schwarz, and Y. Apeloig. J. Am. Chem. Soc. 109, 1317 (1987).
22. P.C. Burgers and J.K. Terlouw. In Encyclopedia of mass spectrometry. Vol. 4. Edited by N.M.M. Nibbering. Elsevier, Amsterdam. 2005. p. 173.
23. (a) L.A. Curtiss, K. Raghavachari, G.W. Trucks, and J.A. Pople. J. Chem. Phys. 98, 1293 (1993);
24. (b) L.A. Curtiss, K. Raghavachari, P.C. Redfern, V. Rassolov, and J.A. Pople. J. Chem. Phys. 109, 7764 (1998);
25. (c) A.G. Baboul, L.A. Curtiss, and P.C. Redfern. J. Chem. Phys. 110, 7650 (1999).
26. (a) J.W. Ochterski, G.A. Petersson, and J.A. Montgomery, Jr. J. Chem. Phys. 104, 2598 (1996);
27. (b) J.A. Montgomery, Jr., M.J. Frisch, J.W. Ochterski, and G.A. Petersson. J. Chem. Phys. 112, 6532 (2000).
28. (a) L.N. Heydorn, Y. Ling, G. de Oliveira, J.M. Martin, C.L. Lifshitz, and J.K. Terlouw. Z. Physik. Chem. (Muenchen), 215, 141 (2001);
29. (b) L.N. Heydorn, P.C. Burgers, P.J.A. Ruttink, and J.K. Terlouw. Int. J. Mass Spectrom. Ion Processes, 228, 759 (2003).
30. C.Y. Wong, P.J.A. Ruttink, P.C. Burgers, and J.K. Terlouw. Chem. Phys. Lett. 387, 204 (2004), and refs. cited therein.
31. D. Suh, P.C. Burgers, and J.K. Terlouw. Int. J. Mass Spectrom. Ion Processes, 144, L1 (1995).
32. (a) J.C. Traeger and R.G. McLoughlin. J. Am. Chem. Soc. 103, 3647 (1981);
33. (b) J.C. Traeger, R.G. McLoughlin, and A.J.J. Nicholson. J. Am. Chem. Soc. 104, 5318 (1982);
34. (c) J.L. Holmes, F.P. Lossing, and P.M. Mayer. J. Am. Chem. Soc. 113, 9723 (1991);
35. (d) F. Turecek and C.J. Cramer. J. Am. Chem. Soc. 117, 12243 (1995);
36. (e) H. Ervasti, P.C. Burgers, and P.J.A. Ruttink. Eur. J. Mass Spectrom. 10, 791 (2004).
37. (a) T. Baer, W.A. Brand, T.L. Bunn, and J.J. Butler. Faraday Discuss. Chem. Soc. 75, 45 (1983);
38. (b) T. Baer and W.L. Hase. Unimolecular reaction dynamics. Oxford University Press, New York. 1996.
39. (a) J.K. Terlouw, W. Heerma, and G. Dijkstra. Org. Mass Spectrom. 16, 326 (1981);
40. (b) D.J. McAdoo and C.E. Hudson. Org. Mass Spectrom. 21, 779 (1986).
41. R. Flammang, M.T. Nguyen, G. Bouchoux, and P. Gerbaux. Int. J. Mass Spectrom. 202, A8 (2000).
42. L.K.M. Kiminkinen, L.C. Zeller, and H.I. Kenttämaa. Chem. Commun. (Cambridge), 466 (1992).
43. M.A. Trikoupis, P.J.A. Ruttink, P.C. Burgers, and J.K. Terlouw. Eur. J. Mass Spectrom. 10, 801 (2004).
44. P.J.A. Ruttink. J. Phys. Chem. 91, 703 (1987).
45. H.F. van Garderen, P.J.A. Ruttink, P.C. Burgers, G.A. McGibbon, and J.K. Terlouw. Int. J. Mass Spectrom. Ion Processes, 121, 159 (1992).
46. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople. Gaussian 03. Revision C.02 [computer program]. Gaussian, Inc., Wallingford, Connecticut. 2004.
47. GAMESS-UK is a package of ab initio programs written by M.F. Guest, J.H. van Lenthe, J. Kendrick, K. Schoffel, and P. Sherwood, with contributions from R.D. Amos, R.J. Buenker, H.J.J. van Dam, M. Dupuis, N.C. Handy, I.H. Hillier, P.J. Knowles, V. Bonacic-Koutecky, W. von Niessen, R.J. Harrison, A.P. Rendell, V.R. Saunders, A.J. Stone, D.J. Tozer, and A.H. de Vries. The package is derived from the original GAMESS code. M. Dupuis, D. Spangler, and J. Wendolowski. GAMESS, Program No. QG01. NRCC software catalogue 1. Vol. 1. 1980.