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A Lithium Amide Protected Against Protonation in the Gas Phase: Unexpected Effect of LiCl

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Lesage, Denis Barozzino Consiglio, Gabriella [UCL] Duwald, Romain Fressigné, Catherine Harrison-Marchand, Anne Gimbert, Yves

In cold THF and in the presence of LiCl, a lithium pyrrolidinylamide forms a 1:1 mixed aggregate, which is observed directly by ESI-MS. Gas-phase protonation of this species leads to selective transfer of H+ to the chlorine, suggesting that LiCl shields the amide nitrogen and prevents its direct protonation.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2015
Language Anglais
Journal information "The Journal of Organic Chemistry" - Vol. 80, no.12, p. 6441-6446 (2015)
Peer reviewed yes
Publisher American Chemical Society (ACS)
issn 0022-3263
e-issn 1520-6904
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
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Bibliographic reference Lesage, Denis ; Barozzino Consiglio, Gabriella ; Duwald, Romain ; Fressigné, Catherine ; Harrison-Marchand, Anne ; et. al. A Lithium Amide Protected Against Protonation in the Gas Phase: Unexpected Effect of LiCl. In: The Journal of Organic Chemistry, Vol. 80, no.12, p. 6441-6446 (2015)
Permanent URL http://hdl.handle.net/2078.1/227835