Gas-phase acidities and sites of deprotonation of 2-ketones and structures of the corresponding enolates

International Journal of Mass Spectrometry

Volumn 227, Issue 3, 2003, Pages 497-508

  Burkell, Jami L ^a   Fridgen, Travis D ^a   McMahon, Terrance B ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

2 Ketones; Gas phase acidity; HPMS

Indexed keywords

2 ALKANONE; ACETONE; ALKANONE; CARBON; CHEMICAL COMPOUND; ENOLATE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENTHALPY; ENTROPY; EXPERIMENTAL TEST; GAS; ION EXCHANGE; MASS SPECTROMETRY; MOLECULAR INTERACTION; MOLECULE; PROTON TRANSPORT; SCALE UP; SOLVATION; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 0038178998     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1387-3806(03)00102-7     Document Type: Article

References (19)

1. Brauman J.I., Blair L.K. J. Am. Chem. Soc. 90:1968;6561.
2. Baker F.W., Parish R.C., Stock L.M. J. Am. Chem. Soc. 89:1967;5677.
3. Wolfe J.F., Staley R.H., Koppel I., Taagapera M., McIver R.T., Beauchamp J.L., Taft R.W. J. Am. Chem. Soc. 99:1977;5417.
4. Taft R.W., Gurka D., Joris L., Schleyer P.V.R., Rakshys J.W. J. Am. Chem. Soc. 91:1969;4801.
5. Cumming J.B., Kebarle P. Can. J. Chem. 56:1978;1.
6. L.G. Wade Jr. (Eds.), Organic Chemistry, Prentice-Hall, Englewood Cliffs, NJ, 1999, p. 166.
7. Chyall L.J., Brickhouse M.D., Schnute M.E., Squires R.R. J. Am. Chem. Soc. 116:1994;8681.
8. Donnelly A., Chowdhury S., Harrison A.G. Org. Mass Spectrum. 24:1989;89.
9. Surig T., Grutzmacher H. Org. Mass Spectrum. 24:1989;851.
10. Karty J.M., Wu Y., Brauman J.I. J. Am. Chem. Soc. 123:2001;9800.
11. Norrman K., McMahon T.B. J. Phys. Chem. A. 103:1999;7009.
12. Gimon-Kinsel M.E., Barbacci D.C., Russell D.H. J. Mass Spectrom. 34:1999;124.
13. Shaffer S.A., Sadilek M., Turecek F., Hop C.E.C.A. Int. J. Mass Spectrom. Ion Processes. 160:1997;137.
14. Craig S.L., Brauman J.I. J. Am. Chem. Soc. 118:1996;6786.
15. Szulejko J.E., Fisher J.J., McMahon T.B., Wronka J. Int. J. Mass Spectrom. Ion Processes. 83:1988;147.
16. Curtiss L.A., Redfern P.C., Raghavachari K., Rassolov V., Pople J.A. J. Chem. Phys. 114:2001;108.
17. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 1998.
18. J.E. Bartmess, in: W.G. Mallard, P.J. Linstrom (Eds.), NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg, MD, 2001 ( http://webbook.nist.gov ).
19. Bartmess J.E., Scott J.A., McIver R.T. Jr. J. Am. Chem. Soc. 101:1979;6046.