Investigation of chemical reactions in solution using API-MS

International Journal of Mass Spectrometry

Volumn 246, Issue 1-3, 2005, Pages 84-104

  Santos, Leonardo Silva ^a   Knaack, Larissa ^a   Metzger, Jürgen O ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

APCI MS; ESI MS; Microreactor; On line screening; Reaction mechanism

Indexed keywords

EID: 26844485585     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2005.08.016     Document Type: Article

References (123)

1. C.M. Whitehouse, R.N. Dreyer, M. Yamashita, and J.B. Fenn Anal. Chem. 57 1985 675
2. J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse Science 246 1989 64
3. R.B. Cole Electrospray Ionization Mass Spectrometry - Fundamentals, Instrumentation, and Applications 1997 Wiley New York
4. J.B. Fenn J. Am. Soc. Mass Spectrom. 4 1993 524
5. E.C. Horning, D.I. Carroll, I. Dzidic, K.D. Haegele, M.G. Horning, and R.N. Stillwell J. Chromatogr. Sci. 12 1974 725
6. D.B. Robb, T.R. Covey, and A.P. Bruins Anal. Chem. 72 2000 3653
7. T.J. Kauppila, T. Kuuranne, E.C. Meurer, M.N. Eberlin, T. Kotiaho, and R. Kostiainen Anal. Chem. 74 2002 5470
8. The term "electrospray ionization" must be understood as the technique and not as the ionization process. Electrospray is not an ionization process in the sense that applies, for example, to electron ionization where the process explicitly concerns the conversion of neutral molecules into ions, except in a small minority of examples.
9. G.J. Van Berkel, S.A. McLuckey, and G.L. Glish Anal. Chem. 64 1992 1586
10. X.M. Xu, S.P. Nolan, and R.B. Cole Anal. Chem. 66 1994 119
11. C. Adlhart, and P. Chen Helv. Chim. Acta 83 2000 2192
12. D.A. Plattner Int. J. Mass Spectrom. 207 2001 125
13. D.A. Plattner Top. Curr. Chem. 225 2003 153
14. D.I. Carroll, I. Dzidic, R.N. Stillwell, K.D. Haegele, and E.C. Horning Anal. Chem. 47 1975 2369
15. G.J. Van Berkel Eur. J. Mass Spectrom. 9 2003 539
16. D. Fabris Mass Spectrom. Rev. 24 2005 30
17. G. Diehl, and U. Karst Anal. Bioanal. Chem. 373 2002 390
18. J.B. Fenn, M. Mann, C.-K. Meng, S.-F. Wong, and C.M. Whitehouse Mass Spectrom. Rev. 9 1990 37
19. J.B. Fenn Angew. Chem. Int. Ed. 42 2003 3871
20. P. Kebarle, and L. Tang Anal. Chem. 65 1993 972
21. S.J. Gaskell J. Mass Spectrom. 32 1997 677
22. Although somewhat modified following ion/molecule reactions in the interface thus are commonly observed as multiply charged species.
23. J.L. Jones, A.R. Dongré, A. Somogyi, and V.H. Wysocki J. Am. Chem. Soc. 116 1994 8368
24. Interception of this process may allow the preservation of relatively strong non-covalent interactions of analytical significance.
25. P. Kebarle, and Y. Ho R.B. Cole Electrospray Ionization Mass Spectrometry 1997 Wiley New York 3 63
26. J.F. de la Mora, G.J. Van Berckel, C.G. Enke, R.B. Cole, M. Martinez-Sanchez, and J.B. Fenn J. Mass Spectrom. 35 2000 939
27. G.J. Van Berkel R.B. Cole Electrospray Ionization Mass Spectrometry 1997 Wiley New York 65 105
28. K. Zang, D.M. Zimmerman, A. Chung-Phillips, and C.J. Cassidy J. Am. Chem. Soc. 115 1993 10812
29. A.T. Blades, P. Jayawera, M.G. Ikonomou, and P. Kebarle J. Chem. Phys. 92 1990 5900
30. L. Gianelli, V. Amendola, L. Fabbrizzi, P. Pallavicini, and G.G. Mellerio Rap. Commun. Mass Spectrom. 15 2001 2347
31. R.W. Vachet, J.A.R. Hartman, and J.H. Callahan J. Mass Spectrom. 33 1998 1209
32. R.W. Vachet, J.R. Hartman, J.W. Gertner, and J.H. Callahan Int. J. Mass Spectrom. 204 2001 101
33. J.R. Hartman, R.W. Vachet, and J.H. Callahan Inorg. Chim. Acta 297 2000 79
34. J.R. Hartman, R.W. Vachet, W. Pearson, R.J. Wheat, and J.H. Callahan Inorg. Chim. Acta 343 2003 119
35. A. Schäfer, B. Fischer, H. Paul, R. Bosshard, M. Hesse, and M. Viscontini Helv. Chim. Acta 75 1992 1955
36. A. Schäfer, H. Paul, B. Fischer, M. Hesse, and M. Viscontini Helv. Chim. Acta 78 1995 1763
37. S.R. Wilson, J. Perez, and A. Pasternak J. Am. Chem. Soc. 115 1993 1994
38. A.O. Aliprantis, and J.W. Canary J. Am. Chem. Soc. 116 1994 6985
39. M. Moreno-Manãs, M. Pérez, and R. Pleixats J. Org. Chem. 61 1996 2346
40. G. Hambitzer, and J. Heitbaum Anal. Chem. 58 1986 1067
41. J.W. Sam, X.-J. Tang, R.S. Magliozzo, and J. Peisach J. Am. Chem. Soc. 117 1995 1012
42. C. Hinderling, and P. Chen Angew. Chem. Int. Ed. 38 1999 2253
43. C. Hinderling, and P. Chen Int. J. Mass Spectrom. 195 2000 377
44. P. Chen Angew. Chem. Int. Ed. 42 2003 2832
45. J. Griep-Raming, S. Meyer, T. Bruhn, and J.O. Metzger Angew. Chem. Int. Ed. 41 2002 2738
46. S. Meyer, and J.O. Metzger Anal. Bioanal. Chem. 377 2003 1108
47. D.J. Wilson, and L. Konermann Anal. Chem. 75 2003 6408
48. R. Arakawa, L. Jian, A. Yoshimura, K. Nozaki, T. Ohno, H. Doe, and T. Matsuo Inorg. Chem. 34 1995 3874
49. R. Arakawa, S. Mimura, G. Matsubayashi, and T. Matsuo Inorg. Chem. 35 1996 5725
50. J. Brum, and P. Dell'Orco Rapid Commun. Mass Spectrom. 12 1998 741
51. P. Dell'Orco, J. Brum, R. Matsuoka, M. Badlani, and K. Muske Anal Chem. 71 1999 5165
52. W. Ding, K.A. Johnson, I.J. Amster, and C. Kutal Inorg. Chem. 40 2001 6865
53. W. Ding, K.A. Johnson, C. Kutal, and I.J. Amster Anal. Chem. 75 2003 4624
54. A.D. Modestov, J. Gun, I. Savotine, and O. Lev J. Electroanal. Chem. 565 2004 7
55. S. Meyer, R. Koch, and J.O. Metzger Angew. Chem. Int. Ed. 42 2003 4700
56. S. Fürmeier, and J.O. Metzger J. Am. Chem. Soc. 126 2004 14485
57. S. Fürmeier, J. Griep-Raming, A. Hayen, and J.O. Metzger Chem. Eur. J. 11 2005 5545
58. A. Hayen, R. Koch, and J.O. Metzger Angew. Chem. Int. Ed. 39 2000 2758
59. A. Hayen, R. Koch, W. Saak, D. Haase, and J.O. Metzger J. Am. Chem. Soc. 112 2000 12458
60. T.F. Hess, T.S. Renn, R.J. Watts, and A.J. Paszczynski Analyst 128 2003 156
61. J. Griep-Raming, and J.O. Metzger Anal. Chem. 72 2000 5665
62. R. Arakawa, S. Tachiyashiki, and T. Matsuo Anal. Chem. 67 1995 4133
63. R. Arakawa, F. Matsuda, G.-E. Matsubayashi, and T. Matsuo J. Am. Soc. Mass Spectrom. 8 1997 713
64. K. Kimura, R. Mizutani, M. Yokoyama, R. Arakawa, G.-E. Matsubayashi, M. Okamoto, and H. Doe J. Am. Chem. Soc. 119 1997 2062
65. R. Arakawa, J. Lu, K. Mizuno, H. Inoue, H. Doe, and T. Matsuo Int. J. Mass Spectrom. Ion Processes 160 1997 371
66. D.I. Schuster, J.R. Cao, N. Kaprinidis, Y.H. Wu, A.W. Jensen, Q.Y. Lu, H. Wang, and S.R. Wilson J. Am. Chem. Soc. 118 1996 5639
67. T.P. Gill, and K.R. Mann Inorg. Chem. 22 1983 1986
68. A.M. McNair, J.L. Schrenk, and K.R. Mann Inorg. Chem. 23 1984 2633
69. D.R. Chrisope, K.M. Park, and G.B. Schuster J. Am. Chem. Soc. 111 1989 6195
70. V. Jakubek, and A.J. Lees Inorg. Chem. 39 2000 5779
71. S.P. Keizer, W.J. Han, and M.J. Stillman Inorg. Chem. 41 2002 353
72. L.S. Santos, C.H. Pavam, W.P. Almeida, F. Coelho, and M.N. Eberlin Angew. Chem. Int. Ed. 43 2004 4330
73. J.S. Hill, and N.S. Isaacs J. Phys. Org. Chem. 3 1990 285
74. H.M.R. Hoffmann, and J. Rabe Angew. Chem. Int. Ed. 22 1983 796
75. M.L. Bode, and P.T. Kaye Tetrahedron Lett. 32 1991 5611
76. Y. Fort, M.-C. Berthe, and P. Caubere Tetrahedron 48 1992 6371
77. H.M.C. Ferraz, F.L.C. Pereira, E.R.S. Gonçalo, L.S. Santos, and M.N. Eberlin J. Org. Chem. 70 2005 110
78. C. Raminelli, M.H.G. Prechtl, L.S. Santos, M.N. Eberlin, and J.V. Comasseto Organometallics 23 2004 3990
79. They also monitored the reaction with ESI-MS in the negative ion mode, but no metal anions were detected.
80. L. Ripa, and A. Hallberg J. Org. Chem. 61 1996 7147
81. J.M. Brown, and K.K. Hii Angew. Chem. Int. Ed. 35 1996 657
82. K.K. Hii, T.D.W. Claridge, and J.M. Brown Angew. Chem. Int. Ed. 36 1997 984
83. Z. Wang, Z.G. Zhang, and X.Y. Lu Organometallics 19 2000 775
84. Z.G. Zhang, X.Y. Lu, Q.H. Zang, and X.L. Han Organometallics 20 2001 3724
85. G.S. Liu, and X.Y. Lu Tetrahedron Lett. 43 2002 6791
86. A. de Meijere, and F.E. Meyer Angew. Chem. Int. Ed. 33 1994 2379 (and references therein)
87. A. Alexakis, J. Berlan, and Y. Besace Tetrahedron Lett. 27 1986 1047
88. A.A. Sabino, A.H.L. Machado, C.R.D. Correia, and M.N. Eberlin Angew. Chem. Int. Ed. 43 2004 2514
89. J. Masllorens, M. Moreno-Manãs, A. Pla-Quintana, and A. Roglans Org. Lett. 5 2003 1559
90. M. Moreno-Manãs, R. Pleixats, R.M. Sebastian, A. Vallribera, and A. Roglans J. Organomet. Chem. 689 2004 3669
91. M.A. Armendia, F. Lafont, M. Moreno-Manãs, R. Pleixats, and A. Roglans J. Org. Chem. 64 1999 3592
92. C. Markert, and A. Pfaltz Angew. Chem. Int. Ed. 43 2004 2498
93. C. Chevrin, J. Le Bras, F. Hénin, J. Muzart, A. Pla-Quintana, A. Roglans, and R. Pleixats Organometallics 23 2004 4796
94. B.F. Bonini, E. Capitò, M. Comes-Franchini, A. Ricci, A. Bottoni, F. Bernardi, G.P. Miscione, L. Giordano, and A.R. Cowley Eur. J. Org. Chem. 2004 4442
95. D.A. Evans, M.C. Kozlowski, J.A. Murry, C.S. Burgey, K.R. Campos, B.T. Connell, and R.J. Staples J. Am. Chem. Soc. 121 1999 669
96. J. Comelles, M. Moreno-Manãs, E. Perez, A. Roglans, R.M. Sebastian, and A. Vallribera J. Org. Chem. 69 2004 6834
97. C. Trage, D. Schröder, and H. Schwarz Chem. Eur. J. 11 2005 619
98. A. Fujii, E. Hagiwara, and M. Sodeoka J. Am. Chem. Soc. 121 1999 5450
99. G. Gerdes, and P. Chen Organometallics 22 2003 2217
100. G. Gerdes, and P. Chen Organometallics 23 2004 3031
101. C. Hinderling, D.A. Plattner, and P. Chen Angew. Chem. Int. Ed. 36 1997 243
102. C. Hinderling, D. Feichtinger, D.A. Plattner, and P. Chen J. Am. Chem. Soc. 119 1997 10793
103. R. Dietiker, and P. Chen Angew. Chem. Int. Ed. 43 2004 5513
104. C.A. Sandoval, T. Ohkuma, K. Muniz, and R. Noyori J. Am. Chem. Soc. 125 2003 13490
105. M. Greb, J. Hartung, F. Köhler, K. Spehar, R. Kluge, and R. Csuk Eur. J. Org. Chem. 2004 3799
106. J. Hartung, and M. Greb J. Organomet. Chem. 661 2002 67
107. J. Hartung, S. Drees, M. Greb, P. Schmidt, I. Svoboda, H. Fuess, A. Murso, and D. Stalke Eur. J. Org. Chem. 2003 2388
108. B.C. Gilbert, J.R.L. Smith, A.M.I. Payeras, J. Oakes, and R.P.I. Prats J. Mol. Catal. A: Chem. 219 2004 265
109. T. Nagataki, Y. Tachi, and S. Itoh J. Mol. Catal. A: Chem. 225 2005 103
110. T. Waters, R.A.J. O'Hair, and A.G. Wedd Chem. Commun. 2000 225
111. T. Kotiaho, M.N. Eberlin, P. Vainiotalo, and R. Kostiainen J. Am. Soc. Mass Spectrom. 11 2000 526
112. E.N. Jacobsen I. Ojima Catalytic Asymmetric Synthesis 1993 VCH Publishers New York 159 202
113. T. Katsuki J. Mol. Catal. A: Chem. 113 1996 87
114. K. Srinivasan, P. Michaud, and J.K. Kochi J. Am. Chem. Soc. 108 1986 2309
115. T.L. Siddall, N. Miyaura, J.C. Huffman, and J.K. Kochi J. Chem. Soc. Chem. Commun. 1983 1185
116. E.G. Samsel, K. Srinivasan, and J.K. Kochi J. Am. Chem. Soc. 107 1985 7606
117. K. Srinivasan, and J.K. Kochi Inorg. Chem. 24 1985 4671
118. D. Feichtinger, and D.A. Plattner Chem. Eur. J. 7 2001 591
119. W. Adam, C. Mock-Knoblauch, C.R. Saha-Moller, and M. Herderich J. Am. Chem. Soc. 122 2000 9685
120. W. Adam, K.J. Roschmann, C.R. Saha-Moller, and D. Seebach J. Am. Chem. Soc. 124 2002 5068
121. J.B. Domingos, E. Longhinotti, T.A.S. Brandão, C.A. Bunton, L.S. Santos, M.N. Eberlin, and F. Nome J. Org. Chem. 69 2004 6024
122. J.B. Domingos, E. Longhinotti, T.A.S. Brandão, L.S. Santos, M.N. Eberlin, C.A. Bunton, and F. Nome J. Org. Chem. 69 2004 7898
123. J.B. Domingos, E. Longhinotti, C.A. Bunton, and F. Nome J. Org. Chem. 68 2003 7051