Electrospray ionization mass spectrometry: A major tool to investigate reaction mechanisms in both solution and the gas phase

European Journal of Mass Spectrometry

Volumn 13, Issue 1, 2007, Pages 19-28

  Eberlin, Marcos N ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Direct infusion electrospray mass spectrometry; Gas phase reactions; Ion chemistry; Reaction intermediates; Reaction mechanisms; Tandem mass spectrometry

Indexed keywords

EID: 34250740975     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.837     Document Type: Article

References (17)

1. J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong and C.M. Whitehouse, "Electrospray Ionization For Mass-Spectrometry of Large Biomolecules", Science 246, 64 (1989).
2. L.S. Santos, L. Knaack and J.O. Metzger, "Investigation of chemical reactions in solution using API-MS2", Int. J. Mass Spectrom. 246, 84 (2005). doi: 10.1016/j.ijms.2005.08.016
3. A.A. Sabino, A.H.L. Machado, C.R.D. Correia and M.N. Eberlin, "Probing the mechanism of the Heck reaction with arene diazonium salts by electrospray mass and tandem mass spectrometry", Angew. Chem. Int. Ed. 43, 2514 (2004). doi: 10.1002/anie.200353076
4. M.N. Eberlin, A.A. Sabino, A.H.L. Machado and C.R.D. Correia, "Probing the intrinsic reactivitiy of Heck reaction intermediates via gas-phase reactions and ESI-MS/MS", submitted.
5. L.S. Santos, C.H. Pavam, W.P. Almeida, F. Coelho and M.N. Eberlin, "Probing the mechanism of the Baylis-Hillman reaction by electrospray ionization mass and tandem mass spectrometry", Angew. Chem. Int. Ed. 43, 4330 (2004). doi: 10.1002/anie.200460059
6. L.S Santos, B.A. DaSilveira Neto, C.S. Consorti, C.H. Pavam, W.P. Almeida, F. Coelho, J. Dupont and M.N. Eberlin "The role of ionic liquids in co-catalysis of Baylis-Hillman reaction: Interception of supramolecular species via electrospray ionization mass spectrometry", J. Phys. Org. Chem. 19, 731 (2006). doi: 10.1002/poc.1066
7. C.A.M. Abella, M. Benassi, L.S. Santos, M.N. Eberlin and F. Coelho, "The Mechanism of Tröger's Bases Formation Probed by Electrospray Ionization Mass Spectrometry", J. Org. Chem. in press, doi: 10.1021/jo062556w
8. C. Raminelli, M.H.G. Prechtl, L.S. Santos, M.N. Eberlin and J.V. Comasseto, "Coupling of vinylic tellurides with alkynes catalyzed by palladium dichloride: Evaluation of synthetic and mechanistic details", Organometallics 23, 3990 (2004). doi: 10.1021/om049805w
9. 4 to Alkynes, Rapid Commun. Mass Spectrom. 21, 1479 (2007). doi: 10.1002/rcm.2984
10. (a) J.B. Domingos, E. Longhinotti, T.A.S. Brandao, L.S. Santos, M.N. Eberlin, C.A. Bunton and F. Nome, "Reaction of bis(2,4-dinitrophenyl) phosphate with hydrazine and hydrogen peroxide. Comparison of O- and N-phosphorylation", J. Org. Chem. 69, 7898 (2004); doi: 10.1021/jo048737k
11. (b) J.B. Domingos, E. Longhinotti, T.A.S. Brandao, L.S. Santos, M.N. Eberlin, C.A. Bunton and F. Nome, "Mechanisms of nucleophilic substitution reactions of methylated Hydroxylamines with bis(2,4-dinitrophenyl)phosphate. Mass spectrometric identification of key intermediates", J. Org. Chem. 69, 6024 (2004). doi: 10.1021/jo0494735
12. I. Dalmazio, L.S. Santos, R. Lopes, M.N. Eberlin and R. Augusti, "Advanced oxidation of caffeine in water: On-line and real-time monitoring by electrospray ionization mass spectrometry", Environ. Sci. Technol. 39, 5982 (2005). doi: 10.1021/es047985v
13. F.C.C. Moura, M.H. Araujo, I. Dalmazio, T.M.A. Alves, L.S. Santos. M.N. Eberlin, R Augusti and R.M. Lago, "Investigation of reaction mechanisms by electrospray ionization mass spectrometry: characterization of intermediates in the degradation of phenol by a novel iron/magnetite/hydrogen peroxide heterogeneous oxidation system", Rapid Commun. Mass Spectrom. 20, 1859 (2006). doi: 10.1002/rcm.2523
14. L.S. Santos, I. Dalmazio, M.N. Eberlin, M. Claeys and R. Augusti, "Mimicking the atmospheric OH-radical-mediated photooxidation of isoprene: formation of cloud-condensation nuclei polyols monitored by electrospray ionization mass spectrometry", Rapid Commun. Mass Spectrom. 20, 2104 (2006). doi: 10.1002/rcm.2574
15. C.D.F. Milagre, H.M.S. Milagre, L.S. Santos, M.L.A. Lopes, P.J.S. Moran, M.N. Eberlin and J.A.R. Rodrigues, "Probing the mechanism of direct Mannich-type α-methylenation of ketoesters via electrospray ionization mass spectrometry", J. Mass Spectrom. in press.
16. G.W. Amarante, M. Benassi, A.A. Sabino, P.M. Esteves, M.N. Eberlin and F. Coelho, "Formation of substituted jV-oxide hydroxyquinolines from o-nitrophenyl Baylis-Hillman adduct: a new key intermediate intercepted by ESI-(+)-MS(/MS) monitoring", Tetrahedron Lett. 47, 8427 (2006). doi: 10.1016/j.tetlet.2006.09.037
17. M.N. Eberlin, L.S. Santos, G.B. Rosso and R.A. Pilli, "The mechanism of the Stille reaction investigated by electrospray ionization mass spectrometry", J. Org. Chem., in press.