Novel β-distonic radical cations [CnH2n+2S]·+ (n = 2, 3) formed upon decarbonylation of ionized S-alkyl thioformates: A mass spectrometric and ab initio study

Journal of Physical Chemistry A

Volumn 101, Issue 50, 1997, Pages 9818-9823

  Flammang, Robert ^a   Lahem, Driss ^a   Nguyen, Minh Tho ^b  

^a UNIVERSITY OF MONS   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; DISSOCIATION; HYDROGEN SULFIDE; INTERFACIAL ENERGY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NITROGEN OXIDES; PARAFFINS;

DECARBONYLATION; DISTONIC RADICAL CATIONS; THIOFORMATES;

SULFUR COMPOUNDS;

EID: 0031338042     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp971883s     Document Type: Article

References (42)

1. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805.
2. Hammerum, S. Mass Spectrom. Rev. 1988, 7, 123.
3. Stirk, K. M.; Kiminkinen, L. K. M.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
4. Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1976, 98, 6331.
5. Bouma, W. J.; Nobes, R. H.; Radom, L. J. Am. Chem. Soc. 1983, 105, 1743.
6. Terlouw, J. K.; Heerma, W.; Dijkstra, G. Org. Mass Spectrom. 1981, 16, 326.
7. Stirk, K. G.; Kenttämaa, H. I. J. Phys. Chem. 1992, 96, 5272.
8. Hoz, T.; Sprecher, M.; Basch, H. J. Mol. Struct. 1987, 150, 51.
9. Lahem, D.; Flammang, R.; Van Haverbeke, Y.; Nguyen, M. T. Rapid Commun. Mass Spectrom. 1997, 11, 373.
10. Lahem, D.; Flammang, R.; Nguyen, M. T. Bull. Soc. Chim. Belg., in press.
11. Flammang, R.; Van Haverbeke, Y.; Braybrook, C.; Brown, J. Rapid Commun. Mass Spectrom. 1995, 9, 795.
12. (a) Bateman, R. H.; Brown, J.; Lefevere, M.; Flammang, R.; Van Haverbeke, Y. Int. J. Mass Spectrom. Ion Processes 1992, 115, 205.
13. (b) Brown, J.; Flammang, R.; Govaert, Y.; Plisnier, M.; Wentrup, C.; Van Haverbeke, Y. Rapid Commun. Mass Spectrom. 1992, 6, 249.
14. Gerbaux, P.; Van Haverbeke, Y.; Flammang, R.; Wong, M. W.; Wentrup, C. J. Phys. Chem. 1997, 101, 6970.
15. Bax, P. C.; Holsboer, D. H.; Van der Veek, A. P. M. Rec. Trav. Chim. 1971, 90, 562.
16. Frisch, M. J. L.; 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.; Nanayakkari, 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 C.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
17. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250.
18. Nguyen, M. T.; Landuyt, L.; Vanquikenborne, L. G. Chem. Phys. Lett. 1991, 182, 275.
19. Holmes, J. L.; Lossing, F. P.; Terlouw, J. K.; Burgers, P. C. Can. J. Chem. 1983, 61, 2305.
20. Beranovà, S.; Wesdemiotis, C. J. Am. Soc. Mass Spectrom. 1994, 5, 1093.
21. (a) Wiedman, F. A.; Cai, J.; Wesdemiotis, C. Rapid Commun. Mass Spectrom. 1994, 8, 804.
22. (b) Flammang, R.; Van Haverbeke, Y.; Wong, M. W.; Wentrup, C. Rapid Commun. Mass Spectrom. 1995, 9, 203.
23. Heinrich, N.; Drewello, T.; Burgers, P. C.; Morrow, J. C.; Schmidt, J.; Kulik, W.; Terlouw, J. K.; Schwarz, H. J. Am. Chem. Soc. 1992, 114, 3776.
24. Lahem, D.; Flammang, R.; Nguyen, M. T. Chem. Phys. Lett. 1997, 270, 83.
25. Weiske, T.; van der Wel, H.; Nibbering, N. M. M.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 733.
26. Gerbaux, P.; Van Haverbeke, Y.; Flammang, R. J. Mass Spectrom. 1997, 32, 1170.
27. Baumann, B. C.; MacLeod, J. K., Radom, L. J. Am. Chem. Soc. 1980, 102, 7927.
28. Verma, S.; Ciupek, J. D.; Cooks, R. G. Int. J. Mass Spectrom. Ion Processes 1984, 62, 219.
29. Bouchoux, G. Mass Spectrom. Rev. 1988, 7, 1.
30. Kiminkinen, L. K. M.; Stirk, K. G.; Kenttämaa, H. I. J. Am. Chem. Soc. 1992, 114, 2027.
31. Kenttämaa, H. I.; Kiminkinen, L. K. M.; Orlowski, J. C.; Stirk, K. M. Rapid Commun. Mass Spectrom. 1992, 6, 734.
32. Vogt, J.; Williamson, A. D.; Beauchamp, J. L. J. Am. Chem. Soc. 1978, 100, 3478.
33. Armitage, M. A.; Higgins, M. J.; Lewars, E. G.; March, R. E. J. Am. Chem. Soc. 1980, 102, 5064.
34. Iraqi, M.; Lifshitz, C.; Reuben, B. G. J. Phys. Chem. 1991, 95, 7742.
35. Wentrup, C.; Gross, G.; Berstermann, H.-M.; Lorencak, P. J. Org. Chem. 1985, 50, 2877.
36. Maquestiau, A.; Pauwels, P.; Flammang, R.; Lorencak, P.; Wentrup, C. Org. Mass Spectrom. 1986, 21, 259.
37. Postma, R.; van Helden, S. P.; van Lenthe, J. H.; Ruttink, P. J. A.; Terlouw, J. K.; Holmes, J. L. Org. Mass Spectrom. 1988, 23, 503.
38. Holmes, J. L.; Osborne, A. D. Int. J. Mass Spectrom. Ion Phys. 1977, 23, 189.
39. · radical has recently been shown to exist as a metastable species: Sadilek, M.; Turecek, F. J. Phys. Chem. 1996, 100, 15027. See also Nguyen, V. Q.; Sadilek, M.; Ferrier, J.; Frank, A. J.; Turecek, F. J. Phys. Chem. 1997, 101, 3789.
40. · radical has recently been shown to exist as a metastable species: Sadilek, M.; Turecek, F. J. Phys. Chem. 1996, 100, 15027. See also Nguyen, V. Q.; Sadilek, M.; Ferrier, J.; Frank, A. J.; Turecek, F. J. Phys. Chem. 1997, 101, 3789.
41. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.
42. Soh, E.; Mayer, P. M.; Baer, T. Int. J. Mass Spectrom. Ion Processes 1997, 160, 63.