Ji, Pengju, Powles, Nicholas, Atherton, John H. and Page, Michael I. (2011) Ionization of Carbon Acids in Liquid Ammonia. Organic Letters, 13 (22). pp. 6118-6121. ISSN 1523-7060

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 pKas in LNH3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pKa 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.