Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities

Matthias C, Kuck D (2009)
CROATICA CHEMICA ACTA 82(1): 7-19.

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Gaseous ion/neutral (1/N) complexes [R+ center dot center dot center dot C6H5CH2CH2CH2C6H5] with R = t-C4H9+, s-C4H9+ and.s-C3H7+ have been generated by protonation of the corresponding precursor compounds, R-C6H4CH2CH2CH2C6H5, in the chemical ionisation (CI) source of a sector-field mass spectrometer. The fragmentation of these I/N complexes and several deuterium-labelled isotopologues on the metastable ions' timescale (20-30 mu s), as studied by MIKE spectrometry, revealed that (i) the initial ring position (meta- or para-) of R = t-C4H9+ does not affect their infra-complex reactivity, (ii) the fragmentation of the s-C3H7+ and s-C4H9+ ions is dominated by proton transfer to the 1,3-diphenylpropane neutral but hydride ion abstraction in the reverse direction competes to a minor extent, (iii) the secondary alkyl cations exhibit the same regioselectivity (k(alpha-H)/k(omega-H) = 1.0) and kinetic isotope effect (k(H)/k(D) = 1.6) in the hydride transfer channel as do tertiary alkyl cations, (iv) the s-C4H9+ ions do not undergo skeletal isomerisation to t-C4H9+ ions within the IN complex. Attempts to characterise the trimethylsilyl complex, [Si(CH3)(3)(+) center dot center dot center dot C6H5CH2CH2CH2C6H5], by CI/MIKE: spectrometry under analogous conditions failed.
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Matthias C, Kuck D. Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities. CROATICA CHEMICA ACTA. 2009;82(1):7-19.
Matthias, C., & Kuck, D. (2009). Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities. CROATICA CHEMICA ACTA, 82(1), 7-19.
Matthias, C., and Kuck, D. (2009). Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities. CROATICA CHEMICA ACTA 82, 7-19.
Matthias, C., & Kuck, D., 2009. Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities. CROATICA CHEMICA ACTA, 82(1), p 7-19.
C. Matthias and D. Kuck, “Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities”, CROATICA CHEMICA ACTA, vol. 82, 2009, pp. 7-19.
Matthias, C., Kuck, D.: Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities. CROATICA CHEMICA ACTA. 82, 7-19 (2009).
Matthias, Carsten, and Kuck, Dietmar. “Gaseous [CnH2n+1+ center dot center dot center dot 1,3-Diphenylpropane] Ion/Neutral Complexes Containing Alkyl Cations of Different Acidities and Hydride Ion Affinities”. CROATICA CHEMICA ACTA 82.1 (2009): 7-19.
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