Unimolecular chemistry of protonated diols in the gas phase: Internal cyclization and hydride ion transfer

Journal of Physical Chemistry A

Volumn 101, Issue 23, 1997, Pages 4271-4282

  Bouchoux, G ^a   Choret, N ^a   Flammang, R ^b  

^a ECOLE POLYTECHNIQUE   (France)

^b UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001089084     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp970479q     Document Type: Article

References (41)

1. (a) Splitter J. S.; Turecek, F. Applications of Mass Spectrometry to Organic Stereochemistry; VCH Publishers, Inc.: New York, 1994.
2. (b) Eichmann E. S.; Alvarez, E.; Brodbelt, J. S. J. Am. Soc. Mass Spectrom. 1992, 3, 535.
3. (c) Chen, Q. F.; Stone, J. A. J. Phys. Chem. 1995, 99, 1442.
4. (d) Ashkenazi P.; Domon, B.; Gutman, A. L.; Mandelbaum, A.; Mueller, D.; Richter, W. J.; Ginsburg, D. Isr. J. Chem. 1989, 29, 131.
5. (a) Bartok, M.; Molnar, A. Chemistry of Ethers, Crown Ethers, Hydrotyl Groups Their Sulphur Analogues; Pataï, S., Ed.; Wiley: Chichester, U.K., 1980; Vol. 2, pp 721-60.
6. (b) Diab, J.; Abou-Assali, M.; Gervais, C.; Anker, D. Tetrahedron Lett. 1985, 26, 1501.
7. (c) Kotkar, D.; Ghosh, P. K. J. Chem Soc Chem. Commun. 1986, 650.
8. (d) Bezouhanova, C. P.; Jabur, F. A. React. Kinet. Catal. Lett. 1993, 51, 177.
9. (e) Wali, A.; Ganeshpure, P. A.; Muthukumaru Pillai, S.; Satish, S. Ind. Eng. Chem. Res. 1994, 33, 444.
10. (a) 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. 1.
11. (b) Szulejko, J. E.; McMahon, T. B. J. Am. Chem. Soc. 1993, 115, 7839.
12. (a) Wesdemiotis, C.; McLafferty, F. W. Chem. Rev. 1987, 87, 485.
13. (b) Terlouw, J. K.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 805.
14. (c) Holmes, J. L. Mass Spectrom. Rev. 1989, 8, 513.
15. (d) McLafferty, F. W. Science 1990, 247, 925.
16. (e) Goldberg, N.; Schwarz, H. Acc. Chem. Res. 1994, 27, 347.
17. (f) Flammang, R.; Gallez, L.; Van Haverbeke, Y.; Wong, M. W.; Wentrup C. Rapid Commun. Mass Spectrom. 1996, 10, 232.
18. Holmes, J. L.; Osborne, A. D. Int. J. Mass Spectrom. Ion Processes 1977, 23, 189.
19. Bateman, R. H.; Brown, J.; Lefevere, M.; Flammang R.; Van Haverbeke, Y. Int. J. Mass Spectrom. Ion Processes 1992, 115, 205.
20. Frisch M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheesemann, 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.; Gonzales, C.; Pople, J. A. Gaussian 94 Revision, Gaussian, Inc., Pittsburgh, PA, 1995.
21. (a) McLafferty, F. W.; Kornfeld, R.; Haddon, W. F.; Levsen K.; Sakai, I.; Bente, P. F., III; Tsai S.-C.; Schuddemage H. D. R. J. Am. Chem. Soc. 1973, 95, 3886.
22. (b) Van de Graaf, B.; Dymerski, P. P.; McLafferty, F. W. J. Chem. Soc., Chem. Commun. 1975, 978.
23. (c) Burgers, P. C.; Terlouw, J. K.; Holmes, J. L. Org. Mass Spectrom. 1982, 17, 369.
24. (d) Poke, M. J.; Cordero, M. M.; Wesdemiotis, C.; Bott, P. A. Int. J. Mass Spectrom. Ion Processes 1992, 113, 35.
25. Bouchoux, G.; Jezequel, S.; Penaud-Berruyer, F. Org. Mass Spectrom. 1993, 28, 421.
26. Ford, G. P.; Smith, C. T. J. Am. Chem. Soc. 1987, 109, 1325.
27. Nakamura, K.; Osamura, Y. J. Phys. Org. Chem. 1990, 3, 737.
28. (a) Nobes, H. R.; Rodwell, W. R.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1981, 103, 1913.
29. (b) Bock, C. W.; George, P.; Glusker, J. P. J. Org. Chem. 1993, 58, 5816.
30. (c) Curtiss, L. A.; Lucas, D. J.; Pople, J. A. J. Chem. Phys. 1995, 102, 3292.
31. Forst, W. Theory of Unimolecular Reactions; Academic Press: New York, 1973.
32. Stein, S. E.; Rabinovitch, B. S. J. Chem. Phys. 1973, 58, 2438.
33. (a) Klots, C. E. J. Chem. Phys. 1973, 58, 5364.
34. (b) Baer, T. Adv. Chem. Phys. 1986, 64, 111.
35. (a) McLafferty, F. W.; Sakai, I. Org. Mass Spectrom. 1973, 7, 971.
36. (b) Harrison, A. G.; Gaumann, T.; Stahl, D. Org. Mass Spectrom. 1983, 18, 517.
37. Lin, P.; Kenttämaa, H. I. J. Phys. Org. Chem. 1992, 5, 201.
38. Maquestiau, A.; Beugnies, D.; Flammang, R.; Houriet, R.; Bouchoux, G. Rapid Commun. Mass Spectrom. 1988, 2, 176.
39. Baer, T.; Brand, W. A.; Bunn, T. L.; Butler, J. J. Faraday Discuss. Chem. Soc. 1983, 75, 45, see also: (a) Miller, A. R. J. Chem. Phys. 1976, 65, 2216. (b) Chesnavich, W. J.; Bowers, M. T. J. Am. Chem. Soc. 1977, 99, 1705.
40. Baer, T.; Brand, W. A.; Bunn, T. L.; Butler, J. J. Faraday Discuss. Chem. Soc. 1983, 75, 45, see also: (a) Miller, A. R. J. Chem. Phys. 1976, 65, 2216. (b) Chesnavich, W. J.; Bowers, M. T. J. Am. Chem. Soc. 1977, 99, 1705.
41. Baer, T.; Brand, W. A.; Bunn, T. L.; Butler, J. J. Faraday Discuss. Chem. Soc. 1983, 75, 45, see also: (a) Miller, A. R. J. Chem. Phys. 1976, 65, 2216. (b) Chesnavich, W. J.; Bowers, M. T. J. Am. Chem. Soc. 1977, 99, 1705.