Abstract
The study of acid-base properties of isolated systems have resulted in a fast growing output of data obtained in high pressure mass spectrometers and in low pressure ion cyclotron resonance spectrometers (ICR), (see Ref. 1 for recent reviews). These studies provide the basis for evaluating intrinsic substituent effects and Taft et al. [2] have recently stressed the predominance of polarization effects over polar (inductive) effects in stabilizing charged species. Subsequent comparison of gas phase and condensed phase data have the potentiality of disclosing solvent effects operating in the condensed phase [3]. While the understanding of the basic properties of monofunctional compounds is a relatively unambiguous matter, the situation becomes evidently more complex in multifunctional systems. Recent examples of the latter are provided by the ketene molecule in which it was found that the carbonyl group is less basic than the methylene group by 18 ± 8 kcal/mol [4], and also by enamine systems where the N-site was found to be less basic than the p-C-site by approximately 9 kcal/mol [5].
Lausanne
Berlin
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
“Gas-Phase Ion Chemistry”, M.T. Bowers, Ed., Chapters 9–11, Academic Press, New York (1979).
R.W. Taft, M. Taagepera, J.L.M. Abboud, J.F. Wolf, D.J. DeFrees, W.J. Hehre, J.E. Bartmess and R.T. Mclver Jr., J. Am. Chem. Soc. 100 (1978) 7767.
E.M. Arnett, Acc. Chem. Res. 6 (1973) 404
P. Kebarle, W.R. Davidson, J. Sunner and S. Meza-Höjer, Pure Appl. Chem. 51 (1979) 63.
J. Vogt, A.D. Williamson and J.L. Beauchamp, J. Am. Chem. Soc, 97 (1975) 6682.
R. Houriet, J. Vogt and E. Haselbach, Chimia 34 (1980) 277.
J.F. Wolf, R.H. Staley, I. Koppel, M. Taagepera, R.T. Mclver Jr., J.L. Beauchamp and R.W. Taft, J. Am. Chem. Soc. 99 (1977) 5417.
R. Houriet, H. Schwarz, W. Zummack, J. G. Andrade and P.v.R. Schleyer, Nouv. J. Chim., in press.
T.B. McMahon and J.L. Beauchamp, Rev. Sci. Instr., 43 (1972) 509.
R. Houriet, H. Schwarz and W. Zuramack, Angew. Chem. 92 (1980) 934
R. Houriet, H. Schwarz and W. Zuramack, Angew. Chem. Int. Ed. Engl. 19 (1980) 905.
P. Politzer and H. Weinstein, Tetrahedron, 31 (1975) 915.
See for example, T.A. Lehman and M.M. Bursey, “Ion Cyclotron Resonance Spectrometry”, Wiley-Interscience, New York (1976).
See for example D.K. Bohme, G.I. Mackay and H.I. Schiff, J. Chem. Phys. 73 (1980) 4976.
For leading articles on “homoconjugation” see P.R. Story and B.C. Clark Jr., in “Carbonium Ions”, p. 1007, G.A. Olah and P.V.R. Schleyer, eds., Wiley-Interscience, New York (1972) and references cited therein.
F.P. Lossing and J.C. Traeger, J. Am. Chem. Soc. 97 (1975) 1579.
J.D. Cox and G. Pilcher, “Thermochemistry of Organic and Organometallic Compounds”, Academic Press, New York (1970).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1982 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Houriet, R., Schwarz, H. (1982). Site of Protonation in Gaseous Five-Membered Ring Systems C4H4X(X=NH,O,S,CH2). In: Ion Cyclotron Resonance Spectrometry II. Lecture Notes in Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-50207-1_12
Download citation
DOI: https://doi.org/10.1007/978-3-642-50207-1_12
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-11957-9
Online ISBN: 978-3-642-50207-1
eBook Packages: Springer Book Archive