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

Lesage, Denis;Barozzino Consiglio, Gabriella;Duwald, Romain;Fressigné, Catherine;Gimbert, Yves;et.al.
(2015) The Journal of Organic Chemistry — Vol. 80, n° 12, p. 6441-6446 (2015)

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Abstract
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.
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Lesage, D., Barozzino Consiglio, G., Duwald, R., Fressigné, C., Harrison-Marchand, A., Faull, K. F., Maddaluno, J., & Gimbert, Y. (2015). A Lithium Amide Protected Against Protonation in the Gas Phase: Unexpected Effect of LiCl. The Journal of Organic Chemistry, 80(12), 6441-6446. https://doi.org/10.1021/acs.joc.5b00875 (Original work published 2015)