Study of the ESI-mass spectrometry ionization mechanism of Fischer carbene complexes

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5269-5277

  Wulff, William D ^a   Korthals, Keith A ^a   Martínez Álvarez, Roberto ^b   Gómez Gallego, Mar ^b   Fernández, Israel ^b   Sierra, Miguel A ^b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; DEUTERIUM; ELECTRON TRANSITIONS; HYDROGEN; IONIZATION; MASS SPECTROMETRY; NEGATIVE IONS; ORGANIC SOLVENTS; PROBABILITY DENSITY FUNCTION;

CARBENE COMPLEXES; ELECTROSPRAY IONIZATION-MASS SPECTROMETRY; HYDROQUINONE (HQ); TETRAHYDROFULVALENE (TTF);

CARBON;

ALLENE DERIVATIVE; ANION; CARBENOID; CHROMIUM; DEUTERIUM; HYDROGEN; HYDROQUINONE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY;

EID: 20844435146     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050553y     Document Type: Article

References (32)

1. Gaskell, S. J. Mass Spectrom. 1997, 32, 677.
2. Vincenti, M. Mass Spectrom. 1995, 30, 925.
3. Schiller, J.; Arnold, K. Encyclopedia of Analytical Chemistry; Meyers, R. A., Ed.; Wiley: Chichester, 2000.
4. (a) Meyer, S.; Koch, R.; Metzger, J. O. Angela. Chem., Int. Ed. 2003, 42, 4700.
5. (b) Traeger, J. C. Int. J. Mass Spectrom. 2000, 200, 387.
6. Van Berkel, G. J., Electrospray Ionization Mass Spectrometry, Wiley: New York, 1997.
7. (a) Martínez-Álvarez, R.; Gómez-Gallego, M.; Fernández, I.; Mancheno, M. J.; Sierra, M. A. Organometallics 2004, 26, 4647.
8. (b) Sierra, M. A.; Gómez-Gallego, M.; Mancheño, M. J.; Martínez-Alvarez, R.; Ramírez-López, P.; Kayali, N.; Gonzalez, A. J. Mass. Spectrom. 2003, 38, 151.
9. Krusic, P. J.; Klabunde, U.; Casey, C. P.; Block, T. F. J. Am. Chem. Soc. 1976, 98, 2015.
10. Lee, S.; Cooper, N. J. J. Am. Chem. Soc. 1990, 112, 9419.
11. (a) Fuchibe, K.; Iwasawa, N. Org. Lett. 2000, 2, 3297.
12. (b) Fuchibe, K.; Iwasawa, N. Chem. Eur. J. 2003, 9, 905.
13. Sierra, M. A.; Ramírez-López, P.; Gómez-Gallego, M.; Lejon, T.; Mancheño, M. J. Angew. Chem., Int. Ed. 2002, 41, 3442.
14. (a) Casey, C. P.; Kraft, S.; Powell, D. R. J. Am. Chem. Soc. 2000, 122, 3771.
15. (b) Casey, C. P.; Kraft, S.; Powell, D. R. J. Am. Chem. Soc. 2002, 124, 2584.
16. See: Slum, S. A.; Tan, K. L.; Bergman, R. G. J. Org. Chem. 2003, 68, 4127 and references therein.
17. See, for example: (a) Gatlin, C. J.; Turecek, F.; Vaisar, T. J. Mass Spectrom. 1995, 30, 1617, 1636.
18. (b) Goodwin, L.; Startin, J. R.; Goodall, D. M.; Keely, B. J. Rapid Commun. Mass Spectrom. 2004, 18, 37.
19. (c) Shoeib, T.; Hopkinson, A. C.; Siu, K. W. M. J. Phys. Chem. B 2001, 105, 12399.
20. (d) Shoeib, T.; Cunje, A.; Hopkinson, A. C.; Siu, K. W. M. J. Am. Chem. Soc., Mass Spectrom. 2002, 13, 408.
21. Plattner, D. A. Int. J. Mass Spectrom. 2001, 207, 125.
22. Aumann, R.; Keinen, H. Chem. Ber. 1987, 120, 537.
23. r) within a series of closely related reactions. IUPAC Compendium of Chemical Terminology, 2nd ed., Pergamon Press: New York, 1997.
24. See also: Dewar, M. J. S.; Dougherty, R. C. The PMO Theory of Organic Chemistry; Plenum: New York, 1975.
25. (a) Fetizon, M.; Henry, Y.; Moreau, N.; Moreau, G.; Golfier, M.; Prange, T. Tetrahedron 1973, 29, 1011.
26. (b) Macco, A. A.; Brouwer, R. J. D.; Nossin, P. M. M.; Godefroi, E. F.; Buck, H. M. J. Org. Chem. 1978, 43, 1591.
27. (a) Hoskovec, M.; Luxova, A.; Svatos, A.; Boland, W. Tetrahedron 2002, 58, 9193.
28. (b) Chadwick, D. J.; Chambers, J.; Hargrave, He; Meakins, G. D.; Snowden, R. L. J. Chem. Soc., Perkin Trans, 1 1973, 2327.
29. (c) Chadwick, D. J.; Chambers, J.; Meakins, G. D.; Snowden, R. L. J. Chem. Soc., Perkin Trans. 2 1975, 604.
30. Fischer, E. O.; Maasböl, A. J. Organomet. Chem. 1968,12, P15.
31. Chelain, E.; Parlier, A.; Audouin, M.; Rudler, H.; Daran, J. C.; Vaissermann, J. J. Am. Chem. Soc. 1993, 225, 10568.
32. Fischer, E. O.; Kreissl, F. R. J. Organomet. Chem. 1972, 35, C47.