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On the structure of the C2H4O2 neutrals (acetic acid versus 1,1-dihydroxyethene) generated from ionized n

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International Journal of Mass Spectrometry and Ion Processes

Volume 81

, 21 December 1987, Pages 217-225

International Journa…

On the structure of the C2H4O2 neutrals (acetic acid versus 1,1-dihydroxyethene) generated from ionized n-hexanoic acid and n-butyl acetate in the gas phase. Implications for the mechanism of the McLafferty rearrangement

Dedicated to Professor Eldon Ferguson on the occasion of his retirement from NOAA, Boulder, CO, U.S.A.

Abstract

Results are reported of CIDI and NRMS experiments which show that the C2H4O2neutral co-generated with C4H+radical dot8 from the metastable n-hexanoic acid ion and the n-butyl acetate molecular ion is acetic acid and not its stable enol, CH2C(OH)2. This is in marked contrast to the structure of the C2H4O+radical dot2 ion, co-generated with C4H8 from the metastable n-hexanoic acid ion, which was earlier shown to be exclusively the enol form of acetic acid. The implication of this and earlier findings for the mechanism of McLafferty-type processes is discussed and it is suggested that this ubiquitous reaction is more complex than hitherto expected. The reaction may well proceed via long-lived ion/dipole or hydrogen-bridged intermediates.

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