Relative basicities toward metal triflates Lewis acids by electrospray mass spectrometry

Chemical Communications

Volumn 46, Issue 44, 2010, Pages 8472-8474

  Monfardini, Ilaria ^a   Massi, Lionel ^a   Duñach, Elisabet ^a   Olivero, Sandra ^a   Gal, Jean Franois ^b  

^a UNIVERSITÉ DE NICE SOPHIA ANTIPOLIS   (France)

^b UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; CATION; LEWIS ACID; METAL DERIVATIVE; ORGANOPHOSPHATE; PHOSPHATE ACETYLTRANSFERASE; TRIFLUOROMETHANESULFONIC ACID; ZINC;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); ELECTROSPRAY MASS SPECTROMETRY;

EID: 78049404196     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc02673e     Document Type: Article

References (21)

1. S. Kobayashi Eur. J. Org. Chem. 1999 15 27
2. S. Kobayashi M. Sugiura H. Kitagawa W. W. L. Lam Chem. Rev. 2002 102 2227 2302
3. H. Gaspard-Iloughmane C. Le Roux Eur. J. Org. Chem. 2004 2517 2532
4. R. Ghosh S. Maiti J. Mol. Catal. A: Chem. 2007 264 1 8
5. Reactive Intermediates: MS Investigations in Solution, ed., L. S. Santos,, Wiley, Weinheim, 2010
6. I. Monfardini L. Massi P. Trémel A. Hauville S. Olivero E. Duñach J.-F. Gal Rapid Commun. Mass Spectrom. 2010 24 2611 2619
7. This ligand exchange phenomenon was already shown in early studies performed by FAB MS in m-nitrobenzyl alcohol as matrix. H. Tsuruta K. Yamaguchi T. Imamoto Chem. Commun. 1999 1703 1704
8. S. Baumgarten D. Lesage V. Gandon J.-P. Goddard M. Malacria J.-C. Tabet Y. Gimbert L. Fensterbank ChemCatChem 2009 1 138 143
9. C. Trage D. Schröder H. Schwarz Chem.-Eur. J. 2005 11 619 627 The program of the kinetic model was kindly provided by Dr D. Schröder.
10. Trage et al. assume implicitly that solution species have equal ionization efficiencies in the ESI process. Considering the relatively small systems that are examined, the Ion Evaporation Model (IEM) is believed to be the most relevant mechanism. P. Kebarle J. Mass Spectrom. 2000 35 804 817
11. K. R. Chalcraft R. Lee C. Mills P. Britz-McKibbin Anal. Chem. 2009 81 2506 2515
12. It was even recently suggested by the Fenn group that IEM may be the common mechanism of ion formation for a wider range of ions; S. Nguyen J. B. Fenn Proc. Natl. Acad. Sci. U. S. A. 2007 104 1111 1117
13. In addition to the postulated common ionization mechanism, it is anticipated that the ions of comparable chemical structure and size will have similar electrospray-ionization efficiencies; M. Oss A. Kruve K. Herodes I. Leito Anal. Chem. 2010 82 2865 2872
14. By working at standardized concentrations, the ionization efficiencies remain constant from spectra to spectra; L. Tang P. Kebarle Anal. Chem. 1993 65 3654 3668 Therefore, we suggest that the ionization efficiencies of the adducts are very similar and that they do not distort the response of the ion source with regard to the concentrations in solution
15. T. A. Mastryukova M. I. Kabachnik J. Org. Chem. 1971 36 1201 1205
16. T. A Mastryukova M. I. Kabachnik Russ. Chem. Rev. 1969 38 795 811 The substituent constant σ was specially devised by Kabachnik et al. for describing substituents effects on physicochemical properties of phosphoryl compounds. The electron donation for the four substituents of our series is in the order (σ value in parentheses): n-BuO (-0.41) > EtO (-0.21) > MeO (-0.12) > PhO (-0.06).
17. C. Laurence and J.-F. Gal, Lewis Basicity and Affinity Scales: Data and Measurement, Wiley, Chichester, 2010
18. R. W. Taft Prog. Phys. Org. Chem. 1983 14 247 350
19. C. A. Tolman Chem. Rev. 1977 77 313 348
20. J. M. Smith B. C. Taverner N. J. Coville J. Organomet. Chem. 1997 530 131 140
21. K. A. Bunten L. Chen A. L. Fernandez A. J. Poë Coord. Chem. Rev. 2002 233-234 41 51