Issue 1, 1991

The mechanism of water loss from the oxonium ions CH3CH2CH2+O[double bond, length half m-dash]CH2 and (CH3)2CH+O[double bond, length half m-dash]CH2

Abstract

Extensive new 2H-labelling results are reported, which pertain to the mechanism of water expulsion from metastable CH3CH2CH2+O[double bond, length half m-dash]CH2 and (CH3)2CH+O[double bond, length half m-dash]CH2 ions. Detailed mechanisms, involving ion–neutral complexes comprising incipient propyl cations coordinated to formaldehyde, propene attached to protonated formaldehyde, or propene and formaldehyde attached to a common proton, are discussed in the light of the labelling data. Loss of positional integrity of the hydrogen and deuterium atoms within the original propyl groups occurs; it is proposed that this takes place via interconversion of the ion–neutral complexes. The crucial step in water elimination appears to be irreversible reorganization of the proton-bound complex (or an ion–neutral complex of protonated formaldehyde and propene) to the open-chain carbonium ion CH3+CHCH2CH2OH.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1991, 147-151

The mechanism of water loss from the oxonium ions CH3CH2CH2+O[double bond, length half m-dash]CH2 and (CH3)2CH+O[double bond, length half m-dash]CH2

R. D. Bowen, A. W. Colburn and P. J. Derrick, J. Chem. Soc., Perkin Trans. 2, 1991, 147 DOI: 10.1039/P29910000147

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