Electrospray mass spectral fragmentation study of N,N′-disubstituted imidazolium ionic liquids

Journal of the American Society for Mass Spectrometry

Volumn 17, Issue 1, 2006, Pages 85-95

  Lesimple, Alain ^a   Mamer, Orval ^a   Miao, Weishi ^a   Chan, Tak Hang ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; ELECTRONS; ESTERS; HYDROGEN; MASS SPECTROMETRY; POSITIVE IONS;

ELECTROSPRAY MASS SPECTROMETRY; IODOBENZOYL ESTER; IONIC LIQUIDS; MIDAZOLIUM;

NITROGEN COMPOUNDS;

ALCOHOL; BENZYL DERIVATIVE; CARBOXYLIC ACID; ESTER DERIVATIVE; HYDROGEN; IMIDAZOLE DERIVATIVE; IONIC LIQUID; METHYL GROUP;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ESTERIFICATION;

EID: 29744463501     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2005.09.002     Document Type: Article

References (43)

1. J.D. Holbrey, K.R. Seddon The phase behavior of 1-alkyl-3- methylimidazolium tetrafluoroborates, ionic liquids and ionic liquid crystals J. Chem. Soc. Dalton Trans. 19 1999 2133 2139
2. J.S. Wilkes A short story of ionic liquids - from molten salts to neoteric solvents Green Chem 4 2002 73 80
3. R. Sheldon Catalytic reactions in ionic liquids Chem. Commun. 23 2001 2399 2407
4. R.A. Sheldon, R.M. Lau, M.J. Sorgedrager, F. van Rantwijk, K.R. Seddon Biocatalysis in ionic liquids Green Chem 4 2002 147 151
5. P. Wasserscheid, W. Keim Ionic liquids - new "solutions" for transition metal catalysis Angew. Chem. Int. Ed 39 2000 3772 3789
6. S.A. Forsyth, J.M. Pringle, D.R. MacFarlane Ionic liquids - an overview Aust. J. Chem. 57 2004 113 119
7. M. Picquet, D. Poinsot, S. Stutzmann, I. Tkatchenko, I. Tommasi, P. Wasserscheid, J. Zimmerman Ionic liquids Media for better molecular catalysis Topics Catalysis 29 2004 3-4, 139-143
8. J.S. Wilkes Properties of ionic liquids. Solvents for catalysis J. Mol. Catal. A Chem 214 2004 11 17
9. J. Fuller, R.A. Osteryoung The room-temperature ionic liquid 1-ethyl-3-methylimidazolium tetrafluoroborate Electrochemical couples and physical properties J. Electrochem. Soc. 144 1997 3881 3886
10. J. Fuller, A.C. Breda, T. Carlin Ionic. liquid-polymer gel electrolytes from hydrophilic and hydrophobic ionic liquids J. Electroanal. Chem. 459 1998 29 34
11. J.G. Huddleston, H.D. Willauer, R.P. Swatloski, A.E. Visser, R.D. Rogers Room temperature ionic liquids as novel media for "clean" liquid-liquid extraction Chem. Commun. 16 1998 1765 1766
12. A.E. Visser, R.P. Swatloski, W.M. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J.H. Davis, R.D. Rogers Task-specific ionic liquids for the extraction of metal ions from aqueous solutions Chem. Commun. 1 2001 135 136
13. A. Bosmann, L. Datsevich, A. Jess, A. Lauter, C. Schmitz, P. Wasserscheid Deep desulfurization of diesel fuel by extraction with ionic liquids Chem. Commun. 7 2001 2494 2495
14. C. Ye, W. Liu, Y. Chen, L. Yu Room-temperature ionic liquids A novel versatile lubricant Chem. Commun. 21 2001 2244 2245
15. G.A. Baker, S.N. Baker, S. Pandey, F.V. Bright An analytical view of ionic liquids Analyst 130 2005 800 808
16. M. Zabet-Moghaddam, R. Kruger, E. Heinzle, A. Tholey Matrix-assisted laser desorption/ionization mass spectrometry for the characterization of ionic liquids and the analysis of amino acids, peptides, and proteins in ionic liquids J. Mass Spectrom. 39 2004 1494 1515
17. Y.L. Li, M.L. Gross Ionic-liquid matrices for quantitative analysis by MALDI-TOF mass spectrometry J. Am. Soc. Mass Spectrom. 15 2004 1833 1837
18. Y.L. Li, M.L. Gross, F.-H. Hsu Ionic-liquid matrices for improved analysis of phospholipids by MALDI-TOF mass spectrometry J. Am. Soc. Mass Spectrom. 16 2005 679 682
19. S. Carda-Broch, A. Berthod, D.W. Armstrong Ionic matrices for matrix-assisted laser desorption/ionization time-of-flight detection of DNA oligomers Rapid Commun. Mass Spectrom. 17 2003 553 560
20. J. Fraga-Dubreuil, J.P. Bazureau Grafted ionic liquid-phase-supported synthesis of small organic molecules Tetrahedron Lett. 42 2001 6097 6100
21. J. Fraga-Dubreuil, J.P. Bazureau Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to one-pot three component synthesis of a small library of 4-thiazolidinones Tetrahedron 59 2003 6121 6130
22. W. Miao, T.H. Chan Exploration of ionic liquids as soluble supports for organic synthesis. Demonstration with a Suzuki coupling reaction Org. Lett. 5 2003 5003 5005
23. 5-enkephalin J. Org. Chem. 70 2005 3251 3255
24. J.H. Davis Task specific ionic liquids Chem. Lett. 33 2004 1072 1077
25. F. Yi, Y. Peng, G. Song Microwave-assisted liquid-phase synthesis of methyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate using functional ionic liquid as soluble support Tetrahedron Lett. 46 2005 3931 3933
26. L. Wang, Z. Huang First application of ionic liquid to reactions involving organotellurium compounds as intermediates J. Chem. Res. 7 2005 446 448
27. J. Karkkainen, J. Asikkala, R.S. Laitenen, M.K. Lajunen Effect of temperature on the purity of product in the preparation of 1-butyl-3- methylimidazolium based ionic liquids Z. Naturforsch. 59 2004 763 770
28. Z.B. Alfassi, R.E. Huie, B.L. Milman, P. Neta Electrospray ionization mass spectrometry of ionic liquids and determination of their solubility in water Anal. Bioanal. Chem. 377 2003 159 164
29. B.L. Milman, Z.B. Alfassi Detection and identification of cations and anions of ionic liquids using ESI MS and MS/MS Eur. J. Mass Spectrom. 11 2005 35 42
30. G.P. Jackson, D.C. Duckworth Electrospray mass spectrometry of undiluted ionic liquids Chem. Commun. 5 2004 522 523
31. P.J. Dyson, I. Khalaila, S. Luettgen, J.S. McIndoe, Z. Dongbin Direct probe electrospray (and nanospray) ionization mass spectrometry of neat ionic liquids Chem. Commun. 19 2004 2204 2205
32. C.P.G. Butcher Energy-dependant electrospray ionization mass spectrometry Aust. J. Chem. 56 2003 339
33. C.P.G. Butcher, P.J. Dyson, B.F.G. Johnson, P.R.R. Langridge-Smith, J.S. McIndoe, C. Whyte On the use of breakdown graphs combined with energy-dependent mass spectrometry to provide a complete picture of fragmentation processes Rapid Commun. Mass Spectrom. 16 2002 1595 1598
34. O.A. Mamer The thermolytic generation of benzofuran from o-hydroxyacetophenone Can. J. Chem. 50 1972 2513 2516
35. M.C. Law, K.-Y. Wong, T.H. Chan Solvent-free route to ionic liquid precursors using a water-moderated microwave process Green Chem. 4 2002 328 330
36. N. Kimizuka, T. Nakashima Spontaneous self-assembly of glycolipid bilayer membranes in sugar-philic ionic liquids and formation of ionogels Langmuir 17 2001 6759 6761
37. A.M. Leone, S.C. Weatherly, M.E. Williams, H.H. Thorp, R.W. Murray An ionic liquid form of DNA Redox-active molten salts of nucleic acids J. Am. Chem. Soc. 123 2001 218 222
38. J.H. Gross Mass Spectrometry 1st ed. 2004 Springer-Verlag Berlin 296
39. A.M. Duffield, R. Beugelmans, H. Budzikiewicz, D.A. Lightner, D.H. Williams, C. Djerassi Mass spectrometry in structural and stereochemical problems. LXIII. Hydrogen rearrangements induced by electron impact on N-n-butyl and N-n-pentylpyrroles J. Am. Chem. Soc. 87 1965 805 810
40. T.M. Harris, J.C. Randall Deuterium exchange reactions at the 2-position of imidazoles Chem. Ind. 41 1965 1728 1729
41. O.A. Mamer, A. Lesimple Protonated 1-methylimidazole decomposition by electrospray tandem mass spectrometry Rapid Commun. Mass Spectrom. 19 2005 1771 1774
42. Q.N. Porter Mass spectrometry of heterocyclic compounds E.C. Taylor A. Weissberger General Heterocyclic Chemistry Series 2nd ed. 1985 John Wiley and Sons New York 695
43. S. Concannon, V.N. Ramachandran, W.F. Smyth A study of the electrospray ionization of selected coumarin derivatives and their subsequent fragmentation using an ion trap mass spectrometer Rapid Commun. Mass Spectrom. 14 2000 1157 1166