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Ionization of Carbon Acids in Liquid Ammonia

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

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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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Graham Stone
Date Deposited: 11 Oct 2012 08:02
Last Modified: 28 Aug 2021 11:22


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