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Type: Artigo de periódico
Title: Atmospheric pressure Eberlin transacetalization reactions in the heterogeneous liquid/gas phase
Author: Augusti, R
Chen, H
Eberlin, LS
Nefliu, M
Cooks, RG
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)(2)NCO+ 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 Oil the surface of the ESSI-generated droplets interact with gaseous neutral reagents. The Eberlin products dissociate exclusively to re-form the reactant (CH2)(2)NCO+ 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. (C) 2006 Elsevier B.V. All rights reserved.
Subject: Eberlin reaction
ion/molecule reaction
heterogeneous reaction
atmospheric pressure reaction
solvated ion
Country: Holanda
Editor: Elsevier Science Bv
Citation: International Journal Of Mass Spectrometry. Elsevier Science Bv, v. 253, n. 3, n. 281, n. 287, 2006.
Rights: fechado
Identifier DOI: 10.1016/j.ijms.2006.05.005
Date Issue: 2006
Appears in Collections:Unicamp - Artigos e Outros Documentos

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