Ionization of carbon acids in liquid ammonia

Pengju Ji, Nicholas T. Powles, John H. Atherton, Michael I. Page

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Abstract

The acidities of various carbon acids in liquid ammonia (LNH 3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK as in LNH 3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pK a of less than 12 are fully ionized in liquid ammonia. Nucleophilic substitution of benzyl chloride by carbanions in liquid ammonia generates a Brønsted β nuc = 0.38.

Original languageEnglish
Pages (from-to)6118-6121
Number of pages4
JournalOrganic Letters
Volume13
Issue number22
DOIs
Publication statusPublished - 18 Nov 2011

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    Ji, P., Powles, N. T., Atherton, J. H., & Page, M. I. (2011). Ionization of carbon acids in liquid ammonia. Organic Letters, 13(22), 6118-6121. https://doi.org/10.1021/ol2026153