The reaction of Me2F+, Me2Cl+ 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.

[Arene . Me3C+] non-Covalent Complexes in the Gas Phase (Trifluoro)methylation of Tertbutyl-substituted Diphenylalkanes.” / Chiavarino, Barbara; Crestoni, Maria Elisa; Fornarini, Simonetta; D., Kuck. - In: INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES. - ISSN 0168-1176. - STAMPA. - 148(1995), pp. 215-228. [10.1016/0168-1176(95)04249-K]

[Arene . Me3C+] non-Covalent Complexes in the Gas Phase (Trifluoro)methylation of Tertbutyl-substituted Diphenylalkanes.”

CHIAVARINO, Barbara;CRESTONI, Maria Elisa;FORNARINI, Simonetta;
1995

Abstract

The reaction of Me2F+, Me2Cl+ 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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/38385
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