Issue 1, 2011
From the journal:

RSC Advances

Charge-tagged N-heterocyclic carbenes†‡

Yuri E. Corilo,a   Fabiane M. Nachtigall,a   Patricia V. Abdelnur,a   Gunter Ebeling,b   Jairton Dupont*b  and  Marcos N. Eberlin*a  

* Corresponding authors

a ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry University of Campinas - UNICAMP, Campinas, Brazil
E-mail: eberlin@iqm.unicamp.br
Fax: (+) 55 19 3521 3073

b Laboratory of Molecular Catalysis, Institute of Chemistry, Federal university of Rio Grande do Sul - UFRGS, Porto Alegre, Brazil
E-mail: Jairton.dupont@ufrgs.br

Abstract

The interception, formation and characterization of the first stable, long lived charge-tagged N-heterocyclic carbenes of the general type 4x+ (x = 1–3) and analogues is reported. Via ESI(+)-MS of solutions of bromine salts of doubly, triply and quadruply charged imidazolium ion IL (3.Brn, n = 2–4), the isolated 4x+ as well as charged aggregates [3.Br(n−x)]x+ likely to be participating in the [3.Br(n−x)]x+ ⇌ 4x+ + HBr solution equilibrium could be transferred and characterized in the gas phase. Mimicking the solution equilibrium, the gaseous [3.Br(n−x)]x+ were found to dissociate nearly exclusively viaHBr loss during thermal activationvia collisions to form gaseous 4x+, which were found to add to acrolein and acetone.

Graphical abstract: Charge-tagged N-heterocyclic carbenes

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Article information

DOI
https://doi.org/10.1039/C1RA00024A
Article type
Paper
Submitted
11 Apr 2011
Accepted
12 Jun 2011
First published
18 Jul 2011

RSC Adv., 2011,1, 73-78

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Charge-tagged N-heterocyclic carbenes

Y. E. Corilo, F. M. Nachtigall, P. V. Abdelnur, G. Ebeling, J. Dupont and M. N. Eberlin, RSC Adv., 2011, 1, 73 DOI: 10.1039/C1RA00024A

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