[Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes

Chiavarino B, Crestoni ME, Fornarini S, Kuck D (1995)
International Journal of Mass Spectrometry and Ion Processes 148(3): 215-228.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Chiavarino, Barbara; Crestoni, Maria Elisa; Fornarini, Simonetta; Kuck, DietmarUniBi
Abstract / Bemerkung
The reaction of Me2F+, Me2C1+ and CF3+ with p-Me3CC6H4(CH2)n,C6D5 (n = 2, 3) initiates a reaction pattern whose major features are accounted for by the additional electrostatic stabilization afforded by the second (spectator) aromatic ring on ionic intermediates and ion-molecule complexes. The Me3C loss following CX3- (X = H, F) addition to the tert-butyl-substituted ring is significantly reduced with respect to a single-ring model substrate, p-Me3CC6H4Me. [Arene · Me3C+] non-covalent complexes mediate the observed interannular and intermolecular Me3C+ transfer. Unimolecular cleavage of Me3CH from [arene · Me3C+], following side-chain H- abstraction, a major fragmentation pathway under mass spectrometric conditions, is instead largely inhibited in the reported radiolytic experiments. Such behavior is accounted for by the effective stabilization of ion-molecule non-covalent complexes ensured by unreactive collisions with about 1 atm bath gas.
Stichworte
Ion-neutral complexes; Arenium ions; Interannular carbenium ion migration; Isomerization
Erscheinungsjahr
1995
Zeitschriftentitel
International Journal of Mass Spectrometry and Ion Processes
Band
148
Ausgabe
3
Seite(n)
215-228
ISSN
0168-1176
Page URI
https://pub.uni-bielefeld.de/record/1774172

Zitieren

Chiavarino B, Crestoni ME, Fornarini S, Kuck D. [Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes. International Journal of Mass Spectrometry and Ion Processes. 1995;148(3):215-228.
Chiavarino, B., Crestoni, M. E., Fornarini, S., & Kuck, D. (1995). [Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes. International Journal of Mass Spectrometry and Ion Processes, 148(3), 215-228. https://doi.org/10.1016/0168-1176(95)04249-K
Chiavarino, B., Crestoni, M. E., Fornarini, S., and Kuck, D. (1995). [Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes. International Journal of Mass Spectrometry and Ion Processes 148, 215-228.
Chiavarino, B., et al., 1995. [Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes. International Journal of Mass Spectrometry and Ion Processes, 148(3), p 215-228.
B. Chiavarino, et al., “[Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes”, International Journal of Mass Spectrometry and Ion Processes, vol. 148, 1995, pp. 215-228.
Chiavarino, B., Crestoni, M.E., Fornarini, S., Kuck, D.: [Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes. International Journal of Mass Spectrometry and Ion Processes. 148, 215-228 (1995).
Chiavarino, Barbara, Crestoni, Maria Elisa, Fornarini, Simonetta, and Kuck, Dietmar. “[Arene Me3C+] non-covalent complexes in the gas-phase (trifluoro)methylation of tert-butyl-substituted diphenylalkanes”. International Journal of Mass Spectrometry and Ion Processes 148.3 (1995): 215-228.
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