TY  - JOUR
AB  - Gas-phase protonolysis of 1-(4-tert-butylphenyl)-3-phenylpropanes bearing a methyl substituent at one of the arene rings gives rise to competing losses of isobutane and isobutene via intermediate, purely hydrocarbon, ion/molecule complexes [Me3C+C6H5CH2CH2CH2–C6H4CH3]. The hydride transfer within the complexes occurs preferentially from the CH2 group of the methylated benzyl unit (in the order p-CH3 > m-CH3  o-CH3 [almost equal to] H) and irrespective of the ring from which the tert-butyl group has been released originally. The reciprocal proton transfer gains importance with increasing proton affinity of the substituted benzene nucleus (p-CH3 < o-CH3 < m-CH3), again independent of the original substitution pattern. Thus, the reactivity of thetert-butyl cation within the complex (as a Lewis and a Brønsted acid) is governed by the whole of the electrostatically bound 1,3-diarylpropane neutral.
DA  - 1995
DO  - 10.1255/ejms.104
KW  - PI-complexes
KW  - Gas-phase
KW  - Neutral complexes
LA  - eng
IS  - 1
M2  - 445
PY  - 1995
SN  - 1356-1049
SP  - 445-455
T2  - European Mass Spectrometry
TI  - Regioselective hydride abstraction and proton transfer in gaseous ion/molecule complexes: methyl substituent effects on the fragmentation of protonated 1-(4-tert-butylphenyl)-3-phenylpropanes
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-17741596
Y2  - 2024-11-24T22:52:25
ER  -