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

Matthias C, Weniger K, Kuck D (1995)
European Mass Spectrometry 1(1): 445-455.

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Abstract
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.
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Matthias C, Weniger K, Kuck D. 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. European Mass Spectrometry. 1995;1(1):445-455.
Matthias, C., Weniger, K., & Kuck, D. (1995). 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. European Mass Spectrometry, 1(1), 445-455.
Matthias, C., Weniger, K., and Kuck, D. (1995). 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. European Mass Spectrometry 1, 445-455.
Matthias, C., Weniger, K., & Kuck, D., 1995. 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. European Mass Spectrometry, 1(1), p 445-455.
C. Matthias, K. Weniger, and D. Kuck, “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”, European Mass Spectrometry, vol. 1, 1995, pp. 445-455.
Matthias, C., Weniger, K., Kuck, D.: 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. European Mass Spectrometry. 1, 445-455 (1995).
Matthias, Carsten, Weniger, Katrin, and Kuck, Dietmar. “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”. European Mass Spectrometry 1.1 (1995): 445-455.
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