Ionization of carbon acids in liquid ammonia

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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

Fingerprint

liquid ammonia
Ammonia
Ionization
Carbon
ionization
acids
Acids
carbon
Liquids
Dimethyl Sulfoxide
Acidity
acidity
Substitution reactions
chlorides
Nuclear magnetic resonance
substitutes
slopes
nuclear magnetic resonance
Temperature
Water

Cite this

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
Ji, Pengju ; Powles, Nicholas T. ; Atherton, John H. ; Page, Michael I. / Ionization of carbon acids in liquid ammonia. In: Organic Letters. 2011 ; Vol. 13, No. 22. pp. 6118-6121.
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Ji, P, Powles, NT, Atherton, JH & Page, MI 2011, 'Ionization of carbon acids in liquid ammonia', Organic Letters, vol. 13, no. 22, pp. 6118-6121. https://doi.org/10.1021/ol2026153

Ionization of carbon acids in liquid ammonia. / Ji, Pengju; Powles, Nicholas T.; Atherton, John H.; Page, Michael I.

In: Organic Letters, Vol. 13, No. 22, 18.11.2011, p. 6118-6121.

Research output: Contribution to journalArticle

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Ji P, Powles NT, Atherton JH, Page MI. Ionization of carbon acids in liquid ammonia. Organic Letters. 2011 Nov 18;13(22):6118-6121. https://doi.org/10.1021/ol2026153