Solvation in electrospray mass spectrometry: Effects on the reaction kinetics of fragmentation mediated by ion-neutral complexes

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5111-5118

  Tu, Ya Ping ^a   He, Limin ^a   Fitch, William ^a   Lam, Michelle ^a  

^a ROCHE BIOSCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; ENERGY DISSIPATION; IONS; MASS SPECTROMETRY; PHASE TRANSITIONS; REACTION KINETICS; STABILIZATION;

COLLISION-INDUCED DISSOCIATION (CID); ELECTROSPRAY IONIZATION (ESI); ION-NEUTRAL COMPLEXES;

SPRAYING;

AZETIDINE DERIVATIVE; BENZYDAMINE; DIAMINE DERIVATIVE; METHYL GROUP; N,N DIMETHYLAMINOPROPOXYL; N,N DIMETHYLAZETIDINE; N,N,N',N' TETRAMETHYL 1,3 PROPANEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; MATHEMATICAL ANALYSIS; MOLECULAR MODEL; SOLVATION;

EID: 20844461860     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050398n     Document Type: Article

References (77)

1. (a) Abian, J. J. Mass Spectrom. 1999, 34, 157-168.
2. (b) Abian, J.; Oosterkamp, A. J.; Gelpi, E. J. Mass Spectrom. 1999, 34, 244-254.
3. Tomer, K. B. Chem. Rev. 2001, 101, 297-328.
4. Smyth, W. F. Anal. Chim. Acta 2003, 492, 1-16.
5. Kostiainen, R.; Kotiao, T.; Kuuranne, T.; Auriola, S. J. Mass Spectrom. 2003, 38, 357-372.
6. Atcheson, B.; Taylor, P. J.; Pillans, P. I.; Tett, S. E. Anal. Chim. Acta 2003, 492, 157-169.
7. Hopfgartner, G.; Bourgogne, E. Mass Spectrom. Rev. 2003, 22, 195-214.
8. (a) Bruins, A. P. In Electrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation and Applications; Cole, R. B., Ed.; Wiley: New York, 1997; Chapter 3.
9. (b) Bruins, A. P. J. Chromatogr. A 1998, 794, 345-357.
10. (c) Niessen, W. M. A. J. Chromatogr. A 1998, 794, 407-435.
11. Dole, M.; Mack, L. L.; Hines, R. L. J. Chem. Phys. 1968, 49, 2240-2249.
12. (a) Iribarne, J. V.; Thomson, B. A. J. Chem. Phys. 1976, 64, 2287-2294.
13. (b) Thomson, B. A.; Iribarne, J. V. J. Chem. Phys. 1979, 71, 4451-4463.
14. Kebarle, P. J. Mass Spectrom. 2000, 35, 804-817.
15. (a) Thomson, B. A. J. Am. Soc. Mass Spectrom. 1997, 8, 1053-1058.
16. (b) Serani, L.; Lemaire, D.; Laprevote, O. Int. J. Mass Spectrom. 2002, 219, 403-408.
17. (a) Harrison, A. G. Rapid Commun. Mass Spectrom. 1999, 13, 1663-1670.
18. (b) Harrison, A. G. J. Mass Spectrom. 1999, 34, 1253-1273.
19. (c) van Dongen, W. D.; van Wijk, J. I. T.; Green, B. N.; Heerma, W.; Haverkamp, J. Rapid Commun. Mass Spectrom. 1999, 13, 1712-1716.
20. Bure, C.; Lange, C. Curr. Org. Chem. 2003, 7, 1613-1624.
21. (a) Weinmann, W.; Wiedemann, A.; Eppinger, B.; Renz, M.; Svoboda, M. J. Am. Soc. Mass Spectrom. 1999, 10, 1028-1037.
22. (b) Weinmann, W.; Stoertzel, M.; Vogt, S.; Wendt, J. J. Chromatogr. A 2001, 926, 199-209.
23. (c) Weinmann, W.; Stoertzel, M.; Vogt, S.; Svoboda, M.; Schreiber, A. J. Mass Spectrom. 2001, 36, 1013-1023.
24. (d) Bure, C.; Gobert, W.; Lelievre, D.; Delmas, A. J. Mass Spectrom. 2001, 36, 1149-1155.
25. (e) Bristow, A. W. T.; Nichols, W. F.; Webb, K. S.; Conway, B. Rapid Commun. Mass Spectrom. 2002, 16, 2374-2386.
26. Gabelica, V.; De Pauw, E. Mass Spectrom. Rev. In press.
27. (a) Schneider, B. B.; Chen, D. D. Y. Anal. Chem. 2000, 72, 791-799.
28. (b). Schneider, B. B.; Douglas, D. J.; Chen, D. D. Y. Rapid Commun. Mass Spectrom. 2001, 15, 249-257.
29. (a) Collette, C.; De Pauw, E. Rapid Commun. Mass Spectrom. 1998, 12, 165-170.
30. (b) Collette, C.; Drahos, L.; De Pauw, E.; Vekey, K. Rapid Commun. Mass Spectrom. 1998, 12, 1673-1678.
31. (c) Gabelica, V.; De Pauw, E.; Karas, M. Int. J. Mass Spectrom. 2004, 231, 189-195.
32. (d). Naban-Maillet, J.; Lesage, D.; Bossee, A.; Gimbert, Y.; Sztaray, J.; Vekey, K.; Tabet, J. C. J. Mass Spectrom. 2005, 40, 1-8.
33. Laprevote, O.; Ducrot, P.; Thal, C.; Serani, L.; Das, B. C. J. Mass Spectrom. 1996, 31, 1149-1155.
34. (a) Weisz, A.; Cojocaru, M.; Mandelbaum, A. J. Chem. Soc., Chem. Commun. 1989, 331-332.
35. (b) Morlender-Vais, N.; Mandelbaum, A. J. Mass Spectrom. 1999, 34, 291-302.
36. (c) Vais, V.; Etinger, A.; Mandelbaum, A. J. Mass Spectrom. 1999, 34, 755-760.
37. (d) Denekamp, C.; Mandelbaum, A. J. Mass Spectrom. 2001, 36, 422-429.
38. (a) Bohme, D. K.; Mackay, G. I. J. Am. Chem. Soc. 1981, 103, 979-981.
39. (b) Bohme, D. K.; Raksit, A. B.; Mackay, G. I. J. Am. Chem. Soc. 1982, 104, 1100-1101.
40. (c) Bohme, D. K.; Raksit, A. B. J. Am. Chem. Soc. 1984, 106, 3447-3452.
41. (a) Chabinyc, M. L.; Craig, S. L.; Regan, C. K.; Brauman, J. I. Science 1998, 279, 1882-1886.
42. (b) Craig, S.; Brauman, J. I. J. Am. Chem. Soc. 1999, 121, 6690-6699.
43. (c) Regan, C. K.; Craig, S. L.; Brauman, J. I. Science 2002, 295, 2245-2247.
44. Takashima, K.; Riveros, J. M. Mass Spectrom. Rev. 1998, 17, 409-430.
45. Bohme, D. K. Int. J. Mass Spectrom 1992, 115, 95-110.
46. (a) Gauld, J. W.; Audier, H.; Fossey, J.; Radom, L. J. Am. Chem. Soc. 1996, 118, 6299-6300.
47. (b) Gauld, J. W.; Radom, L. J. Am. Chem. Soc. 1997, 119, 9831-9839.
48. Trikoupis, M. A.; Terlouw, J. K.; Burgers, P. C. J. Am. Chem. Soc. 1998, 120, 12131-12132.
49. Tu, Y.-P.; Holmes, J. L. J. Am. Chem. Soc. 2000, 122, 3695-3700; 5597-5602.
50. Williams, D. H. Acc. Chem. Res. 1977, 10, 280-286.
51. (a) Morton, T. H. Tetrahedron 1982, 38, 3195-3243.
52. (b) Morton, T. H. Org. Mass Spectrom. 1992, 27, 353-368.
53. (a) McAdoo, D. J. Mass Spectrom. Rev. 1988, 7, 363-393.
54. (b) McAdoo D. J.; Morton, T. H. Acc. Chem. Res. 1993, 26, 295-302.
55. Bowen, R. D. Acc. Chem. Res. 1991, 24, 364-371.
56. Longevialle, P. Mass Spectrom. Rev. 1992, 11, 157-192.
57. Chalk, A. J.; Radom, L. J. Am. Chem. Soc. 1998, 120, 8430-8437.
58. Holmes, J. L.; Terlouw, J. K. Org. Mass Spectrom. 1980, 15, 383-396.
59. (a) Yost, R. A.; Fetterolf, D. D. Mass Spectrom. Rev. 1983, 2, 1-45.
60. (b) Ospina, M. P.; Powell, D. H.; Yost, R. A. J. Am. Soc. Mass Spectrom. 2003, 14, 102-109.
61. Bouchoux, G.; Choret, N.; Flammang, R. J. Phys. Chem. A 1997, 101, 4271-4282.
62. Bouchoux, G.; Choret, N.; Berruyer-Penaud, F.; Flammang, R. J. Phys. Chem. A 2001, 105, 9166-9177.
63. Bouchoux, G.; Choret, N.; Berruyer-Penaud, F.; Flammang, R. Int. J. Mass Spectrom. 2002, 217, 195-230.
64. +. ion of N-methylazetidine that was generated from the N,N-dimethylazetidine cation precursor. The quaternary ammonium cation loses one methyl upon neutralization (the quaternary ammonium radical is unstable).
65. For a review on neutralization-reionization mass spectrometry, see: Holmes, J. L. Mass Spectrom. Rev. 1989, 8, 513-539.
66. 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), 1-861.
67. Bowen, R. D.; Colburn, A. W.; Derrick, P. J. J. Chem. Soc., Perkin Trans. 2 1993, 2363-2372.
68. Hunter, E. P. L.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413-656.
69. Eiden, G. C.; Weisshaar, J. C. J. Phys. Chem. 1991, 95, 6194-6197.
70. Farrell, P. G.; Newton, J. J. Phys. Chem. 1965, 69, 3506-3509.
71. (a) Rogalewicz, F.; Hoppilliard, Y.; Ohanessian, G. Int. J. Mass Spectrom. 2000, 201, 307-320.
72. (b) Hoppilliard, Y.; Rogalewicz, F.; Ohanessian, G. Int. J. Mass Spectrom. 2001, 204, 267-280.
73. (c) Rogalewicz, F.; Hoppilliard, Y.; Ohanessian, G. Int. J. Mass Spectrom, 2001, 206, 45-52.
74. (d) Rogalewicz, F.; Hoppilliard, Y.; Ohanessian, G. Int. J. Mass Spectrom. 2003, 227, 439-451.
75. Desaire, H.; Leavell, M. D.; Leary, J. A. J. Org. Chem. 2002, 67, 3693-3699.
76. Adhiya, A.; Wesdemiotis, C. Int. J. Mass Spectrom. 2002, 214, 75-88.
77. Rodriguez-Santiago, L.; Noguera, M.; Sodupe, M.; Salpin, J. Y.; Tortajada, J. J. Phys. Chem. 2003, 107, 9865-9874.