Charge-tagged N-heterocyclic carbenes (NHC): Direct transfer from ionic liquid solutions and long-lived nature in the gas phase View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2017-06

AUTHORS

Thyago S. Rodrigues, Denis Lesage, Wender A. da Silva, Richard B. Cole, Günter Ebeling, Jaïrton Dupont, Heibbe C. B. de Oliveira, Marcos N. Eberlin, Brenno A. D. Neto

ABSTRACT

Negatively charge-tagged N-heterocyclic carbenes have been formed in solution via deprotonation of imidazolium ions bearing acid side groups and transferred to the gas phase via ESI(-)-MS. The structure of the putative and apparently stable gaseous carbenes formed in such conditions were then probed via reactions with carbon dioxide using a triple quadrupole mass spectrometer particularly optimized for ion/molecule reactions of ESI-generated ions. Complete conversion to imidazolium carboxylates was achieved, which seems to demonstrate the efficiency of the transfer, the gas-phase stability, and the long-lived nature of these unprecedented charge-tagged carbenes and their predominance in the ionic population. Comprehensive studies on the intrinsic reactivity of N-heterocyclic carbenes with silent charge tags are therefore possible. Graphical Abstract ᅟ. More... »

PAGES

1021-1029

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s13361-017-1637-8

DOI

http://dx.doi.org/10.1007/s13361-017-1637-8

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1084520437

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/28389984


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