Ionization of Carbon Acids in Liquid Ammonia

Ionization of Carbon Acids in Liquid Ammonia

The acidities of various carbon acids in liquid ammonia (LNH3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK as in LNH3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pK a of less...

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Veröffentlicht in:Organic letters 2011-11, Vol.13 (22), p.6118-6121
Hauptverfasser: Ji, Pengju, Powles, Nicholas T, Atherton, John H, Page, Michael I
Format: Artikel
Sprache:eng
Schlagworte:
Ammonia - chemistry
Anions - chemistry
Carbonic Acid - chemistry
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Zusammenfassung:The acidities of various carbon acids in liquid ammonia (LNH3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK as in LNH3 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 βnuc = 0.38.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2026153