The generation, stability, dissociation and ion/molecule chemistry of sulfinyl cations in the gas phase

Journal of the Chemical Society. Perkin Transactions 2

Volumn 4, Issue , 1996, Pages 587-596

  Gozzo, Fábio Cesar ^a   Sorrilha, Ana Elisa P M ^a   Eberlin, Marcos N ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000973964     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29960000587     Document Type: Article

References (74)

1. F. A. Carey and R. J. Sundberg, in Advanced Organic Chemistry, Plenum Press, New York, 1983.
2. G. A. Olah, P. Schilling, P. W. Westrman and H. C. Lin, J. Am. Chem. Soc., 1974, 96, 3581.
3. J. H. Rolston and K. Yates, J. Am. Chem. Soc., 1969, 91, 1469.
4. T. Mukaiyama, Org. React., 1982, 28, 203.
5. (a) C. Mannich and P. Schumann, Chem. Ber., 1936, 69, 2299;
6. (b) F. F. Blicke, Org. React., 1942, 1, 303.
7. (a) G. A. Olah (ed.), Friedel-Crafts and Related Reactions, Wiley, New York, 1964, vol. 3;
8. (b) G. A. Olah, A. Germain and A. M. White, in Carbonium Ions, G. A. Olah and P. V. R. Schleyer (eds.), Wiley, New York, 1976, vol. 5, ch. 35, p. 2049.
9. M. T. Bowers (ed.), in Gas Phase Ion Chemistry, Academic Press, New York, 1979.
10. J. R. Chapman, Practical Organic Mass Spectrometry, Wiley, New York, 1993.
11. R. H. Nobes, W. J. Bouma and L. Radom, J. Am. Chem. Soc., 1983, 105, 309.
12. (a) R. Weber and K. Levsen, Org. Mass Spectrom., 1980, 15, 138;
13. (b) F. Turecek and F. W. McLafferty, Org. Mass Spectrom., 1983, 18, 608;
14. (c) B. V. Baar, P. C. Burgers, J. K. Terlouw and H. Schwarz, J. Chem. Soc., Chem. Commun., 1986, 1607;
15. (d) K. Pihlaja, P. Kuosmanen and P. Vainiotalo, Org. Mass Spectrom., 1988, 23, 770.
16. (a) D. A. Chatfield and M. M. Bursey, J. Am. Chem. Soc., 1976, 98, 6492;
17. (b) R. H. Staley, R. D. Wieting and J. L. Beauchamp, J. Am. Chem. Soc., 1977, 99, 5964;
18. (c) M. Kumakura and T. Sigiura, J. Phys. Chem., 1978, 82, 639;
19. (d) C. Sparapani and M. Speranza, J. Am. Chem. Soc., 1980, 102, 3120;
20. (e) J. K. Kim and M. C. Caserio, J. Am. Chem. Soc., 1982, 104, 4624;
21. (f) M. Attinà and F. Cacace, J. Am. Chem. Soc., 1983, 105, 1122;
22. (g) M. C. Caserio and J. K. Kim, J. Am. Chem. Soc., 1983, 105, 6896;
23. (h) C. Paradisi, H. Kenttämaa, Q. T. Le and M. C. Caserio, Org. Mass Spectrom., 1988, 23, 521;
24. (i) N. A. Rahman, C. L. Fisher and M. C. Caserio, Org. Mass Spectrom., 1988, 23, 517.
25. (a) M. N. Eberlin, T. K. Majumdar and R. G. Cooks, J. Am. Chem. Soc., 1992, 114, 2884;
26. (b) M. N. Eberlin and R. G. Cooks, J. Am. Chem. Soc., 1993, 115, 9226.
27. M. N. Eberlin and R. G. Cooks, Org. Mass Spectrom., 1993, 28, 679.
28. (a) G. A. Olah, G. K. Surya Prakash and T. Nakajima, Angew. Chem., Int. Ed. Engl., 1980, 19, 812;
29. (b) E. Lindner and H.-G. Karmann, Angew. Chem., Int. Ed. Engl., 1968, 7, 548.
30. (a) F. W. McLafferty, Tandem Mass Spectrometry, Wiley, New York, 1983;
31. (b) K. L. Bush, G. L. Glish and S. A. McLuckey, Mass Spectrometry/Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry, VCH, New York, 1989.
32. 3 experiments, their systematic basis and applications, see: J. C. Schwartz, A. P. Wade, C. G. Enke and R. G. Cooks, Anal. Chem., 1990, 62, 1809.
33. (a) J. C. Schwartz, K. L. Schey and R. G. Cooks, Int. J. Mass Spectrom. Ion Processes, 1989, 3, 305;
34. (b) V. F. Juliano, F. C. Gozzo, M. N. Eberlin, C. Kascheres, C. L. do Lago, Anal. Chem., in the press;
35. (c) J. D. Morrison, D. A. Stanney and J. Tedder, Proc. 34th ASMS Conference on Mass Spectrometry and Allied Topics, Cincinnati, OH, 1986, p. 222;
36. (d) C. Beaugrand, G. Devant, Jaouen, D. H. Mestdagh, N. Morin and C. Rolando, Adv. Mass Spectrom., 1989, 11A, 256.
37. (a) B. J. Shay, M. N. Eberlin, R. G. Cooks and C. J. Wesdemiotis, J. Am. Soc. Mass Spectrom., 1992, 3, 518;
38. (b) T. Kotiaho, B. J. Shay, R. G. Cooks and M. N. Eberlin, J. Am. Chem. Soc., 1993, 115, 1004;
39. (c) M. N. Eberlin, T. Kotiaho, B. Shay, S. S. Yang and R. G. Cooks, J. Am. Chem. Soc., 1994, 116, 2457;
40. (d) M. Sablier, L. Capron, H. Mestdgh and C. Rolando, Tetrahedron Lett., 1994, 35, 2895;
41. (e) F. C. Gozzo and M. N. Eberlin, J. Am. Soc. Mass Spectrom., 1995, 6, 554;
42. (f) L. Lu, S. S. Yang, Z. Wang, R. G. Cooks and M. N. Eberlin, J. Mass Spectrom., 1995, 30, 581;
43. (g) S. S. Yang, G. Chen, S. Ma, R. G. Cooks, F. C. Gozzo and M. N. Eberlin, J. Mass Spectrom., 1995, 30, 807.
44. (a) S. Meyerson, H. Drews and E. K. Fields, Anal. Chem., 1964, 36, 1294;
45. (b) R. Appel, H. W. Fehlhaber, D. Häussgen and R. Schöllhorn, Chem. Ber., 1966, 99, 3108
46. (c) P. Potzinger, H. U. Stracke, W. Küpper and K. Z. Gollnick, Z. Naturforch., 1975, 30a, 340;
47. (d) A. M. Peers and J. C. Muller, Int. J. Mass Spectrom. Ion Phys., 1975, 16, 321;
48. (e) R. A. Khmel'nitskii and Yu. A. Efremov, Russ. Chem. Rev., 1977, 46, 46;
49. (f) W. B. Nixon, W. S. Woodward and M. M. Bursey, J. D. Henion, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 115;
50. (g) L. K. Liu and F.-T. Luo, Org. Mass Spectrom., 1983, 18, 22;
51. (h) K. Pihlaja, in The Chemistry of Sulphones and Sulphoxides, S. Patai, Z. Rappoport, C. Stirling, (eds.), ch. 6, p. 125, Wiley, New York, 1988;
52. (i) M. Gu and F. Turecek, J. Am. Chem. Soc., 1992, 114, 7146;
53. (j) R. A. W. Johnstone (ed.), Mass Spectrometry, The Chemical Society, London, 1979, vol. 5, p. 277.
54. (a) L. Carlsen and H. Egsgaard, J. Am. Chem. Soc., 1988, 110, 6701;
55. (b) F. Turecek, D. E. Drinkwater and F. W. McLafferty, J. Am. Chem. Soc., 1989, 111, 7696;
56. (c) G. A. McGibbon, P. C. Burgers and J. K. Terlouw, Chem. Phys. Let., 1994, 218, 499;
57. (d) F. C. Gozzo and M. N. Eberlin, J. Mass Spectrom., 1995, 30, 1553.
58. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
59. SPARTAN, ver. 3.1, Wavefunction, Inc. 18401 Von Karma, suite 370, Irvine, CA 92715, USA.
60. GAUSSIAN92, revision C, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzales, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, GAUSSIAN, Inc., Pittsburgh PA, 1992.
61. (a) W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257;
62. (b) P. C. Hariharan and J. A. Pople, Theor. Chem. Acta, 1973, 72, 650;
63. (c) M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163;
64. (d) M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
65. C. Møller and M. S. Plesset, Phys. Rev. 1934, 46, 618.
66. XMOL, ver. 1.3.1, Minessota Supercomputer Center, Inc., Minneapolis, MN, 1993.
67. F. W. McLafferty and F. Turecek, Interpretation of Mass Spectra, HD Science, New York, 1993.
68. J. H. Bowie, D. H. Willians, S.-O. Lawesson, J. Ø. Madsen, C. Nolde and G. Schroll, Tetrahedron, 1966, 22, 3515.
69. F. C. Gozzo and M. N. Eberlin, Proceedings of the 41st ASMS Conference on Mass Spectrometry and Allied Topics, 1993, 974.
70. M. T. Bogert and R. L. Roblin, J. Am. Chem. Soc., 1933, 55, 3741.
71. H. Budzikiewicz, C. Djerassi and D. H. Williams, Mass Spectrometry of Organic Compounds, Holden-Day, San Francisco, 1967.
72. M. N. Eberlin, N. H. Morgon, S. S. Yang, B. J. Shay and R. G. Cooks, J. Am. Soc. Mass Spectrom., 1995, 6, 1.
73. M. M. Basher, R. S. Pimpim and M. N. Eberlin, submitted for publication.
74. F. Turecek and V. Hanus, Mass Spectrom. Rev., 1984, 3, 85.