Ionization of carbon acids in liquid ammonia.
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(a)s 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.
IPOS, The Page Laboratories, Department of Chemical and Biological Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, United Kingdom.
Pengju
P
Ji
Nicholas T
NT
Powles
John H
JH
Atherton
Michael I
MI
Page
D000641:Ammonia / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D002255:Carbonic Acid / Q000737:chemistry*
D000838:Anions; D002255:Carbonic Acid; D000641:Ammonia