Atmospheric pressure Eberlin transacetalization reactions in the heterogeneous liquid/gas phase

Rodinei Augusti, Hao Chen, Livia Schiavinato Eberlin, Marcela Nefliu, R. Graham Cooks

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19 Scopus citations

Abstract

The Eberlin reaction, the ionic transacetalization of cyclic acetals and analogues with acylium and related ions, is demonstrated in the course of ion/molecule reactions at atmospheric pressure. Selected gaseous acetals (1,3-dioxolane, 2-methyl-1,3-dioxolane, 2,2-dimethyl-1,3-dioxolane, 4-methyl-1,3-dioxolane, 2-phenyl-1,3-dioxolane, 1,3-dioxane, and 1,3,5-trioxane) react efficiently with the (CH3)2NCO+ acylium ion, generated by electrosonic spray ionization (ESSI) of an aqueous/methanol solution of tetramethylurea (TMU), to furnish the characteristic cyclic ionic acetals, the Eberlin products, in moderate to high yields. It is proposed that acylium ions on the surface of the ESSI-generated droplets interact with gaseous neutral reagents. The Eberlin products dissociate exclusively to re-form the reactant (CH3)2NCO+ acylium ion upon collision-induced dissociation (CID), confirming their structures. The intact adduct, i.e., acylium ion plus neutral reagent (the stable precursor of the Eberlin product), is observed in these experiments whereas it is not observed in studies of the same Eberlin reactions under conventional reduced pressure ion/molecule reaction conditions. It is suggested that under atmospheric pressure conditions these intact adducts are likely stabilized through deactivation via collision with buffer gas.

Original languageEnglish (US)
Pages (from-to)281-287
Number of pages7
JournalInternational Journal of Mass Spectrometry
Volume253
Issue number3
DOIs
StatePublished - Jul 1 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Instrumentation
  • Condensed Matter Physics
  • Spectroscopy
  • Physical and Theoretical Chemistry

Keywords

  • Atmospheric pressure reaction
  • Eberlin reaction
  • Heterogeneous reaction
  • Ion/molecule reaction
  • Solvated ion

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