Gas Phase Reactions of Cysteine with Charged Electrophiles: Regioselectivities of the Dimethylchlorinium Ion and the Methoxymethyl Cation

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6112-6120

  Freitas, Michael A ^a   O'Hair, Richard A J ^a   Williams, Todd D ^b  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000020178     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9706741     Document Type: Article

References (52)

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26. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
27. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
28. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
29. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
30. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
31. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
32. +, see: (a) Burinsky, D. J.; Campana, J. E. Org. Mass Spectrom. 1988, 23, 613. (b) Lane, D. C.; McGuire, M. Org. Mass Spectrom. 1983, 18, 494. (c) Isern-Fletcha, I.; Cooks, R. G.; Wood, K. V. Int. J. Mass Spectrom. Ion Proc. 1984, 62, 73. (d) Benezra, S. A.; Hoffmann, M. K.; Bursey, M. M. J. Am. Chem. Soc. 1995, 117, 2071. (e) Speranza, M.; Pepe, N.; Cipollini, R. J. Chem. Soc. Perkin Trans. 2 1979, 1179. (f) Brodbelt, J. S.; Cooks, R. G. Anal. Chim. Acta 1988, 206, 239. (g) Karpas, Z.; Anicich, V. G.; Huntress, W. T. Chem. Phys. Lett. 1978, 59, 84. (h) Karpas, Z. Chem. Phys. Lett. 1985, 120, 53.
33. 2), see: Uggerud, E. J. Chem. Soc. Perkin Trans. 2 1996, 1915.
34. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
35. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
36. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
37. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
38. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
39. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
40. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
41. +, see: (a) Sen Sharma, D. K.; Kebarle, P. J. Am. Chem. Soc. 1982, 104, 19. (b) Morizur, J.-P.; Martigny, I.; Tortajada, J.; Geribaldi, S. Org. Mass Spectrom. 1990, 25, 89. (c) Houriet, R.; Rolli, E.; Flammang, R.; Maquestiau, A.; Bouchoux, G. Org. Mass Spectrom. 1987, 22, 770. (d) Keough, T. Org. Mass Spectrom. 1984, 19, 551. (e) Zappey, H.; Fokkens, R. H.; Ingemann, S.; Nibbering, N. M. M.; Florencio, H. Org. Mass Spectrom. 1991, 26, 587. (f) Angelini, G.; Lilla, G.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 7091. (g) Pepe, N.; Speranza, M. J. Chem. Soc. Perkin Trans. 2 1981, 1430. (h) Occhiucci, G.; Speranza, M.; de Koning, L. J.; Nibbering, N. M. M. J. Am. Chem. Soc. 1989, 111, 7387.
42. (a) For a discussion and compilation of MCA's, see: Bartmess, J. E. Mass Spectrom. Rev. 1989, 8, 297.
43. (b) For experimental gas phase thermochemical data on ions and neutrals, see: Gas-phase Ion and Neutral Thermochemistry. 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.
44. (b) For experimental gas phase thermochemical data on ions and neutrals, see: Gas-phase Ion and Neutral Thermochemistry. 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.
45. -1: Holmes, J. L.; Lossing, F. P.; McFarlane, R. A. Int. J. Mass Spectrom. Ion Proc. 1988, 86, 209.
46. We cannot guarantee that all possible conformations of each of these species have been found.
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48. (b) Eichmann, E. S.; Brodbelt, J. S. J. Am. Soc. Mass Spectrom, 1993, 4, 97.
49. (c) Eichmann, E. S.; Brodbelt, J. S. J. Am. Soc. Mass Spectrom. 1993, 4, 230.
50. +.
51. One of the conformers of H underwent ring opening during the optimization process, yielding a confromer of E as the final optimized geometry. Although we have not searched for a transition state to this process, this suggests a low barrier to ring opening.
52. Maycock, C. D.; Stoodley, R. J. J. Chem. Soc., Pekin Trans. I 1979, 1852.