191232-63-0Relevant academic research and scientific papers
Intramolecular benzyl-benzyl interactions in protonated benzyl diethers in the gas phase. Effects of internal hydrogen bonding
Edelson-Averbukh, Marina,Etinger, Alexander,Mandelbaum, Asher
, p. 1095 - 1105 (2007/10/03)
Protonated molecules of a variety of benzyl diethers, produced by chemical ionization (CI), undergo a unique rearrangement yielding relatively abundant mlz 181 C14H13+ ions, both in the ion source and under collision-induc
Stability and reactivity of the benzyl and tropylium cations in the gas phase
Sharma, D. K. Sen,Kebarle, P.
, p. 1592 - 1601 (2007/10/02)
A measurement of equilibrium : t-C4H9+ + BzCl = t-C4H9Cl + C7H7+ led to equilibrium constants K4 which are fair agreement with earlier work by Abboud at al.However, the present temperature dependence predicts a ΔS40 which is sufficiently different from that by Abboud et al. to put in question the identification of C7H7+ as Bz+ on the basis of the measured ΔS40 value.Therefore experiments were made to confirm that C7H7+ produced in is Bz+ and not the tropylium cation.A C7H7+ cation was produced by hydrid abstraction from 1,3,5-cycloheptatriene.The behaviour of that C7H7+ ion was entirely different from C7H7+ produced by chloride abstraction from BzCl or hydride abstraction from toluene.While the benzyl derived C7H7+ engaged in a number of reactions like hydride abstraction, chloride abstraction, addition, condensation, etc., the C7H7+ from the heptatriene remained completely unreactive.On this basis the C7H7+ ions were identified as Bz+ and tropylium+, respectively.Rate constants for several reactions of Bz+ were determined.It is concluded that a rearrangement from benzyl to tropylium cations and vice versa does not occur at least up to 300 deg C.The ions also retain their identity if they are produced with considerable internal excitation energy.
