Journal of Organic Chemistry p. 1074 - 1076 (1991)
Update date:2022-08-02
Topics:
Streitwieser, Andrew
Ciula, James C.
Krom, James A.
Thiele, Georg
A revised cesium ion pair acidity scale relative to fluorene at pKa = 22.90 is presented.The range of the scale is extended 3 pK units by including more acidic indicators and now encompasses pKas from 15.62 to 38.73.The accuracy of the scale has been improved by multiple equilibria among indicators.Uncertainties between close lying indicators is generally less than +/-0.01 pK unit.Broensted plots are constructed for series of fluorenyl and arylmethyl hydrocarbons.From these plots, the acidity value for toluene in THF was extrapolated (pKa = 40.9).Comparisons are drawn to ionic acidities in dimethyl sulfoxide.
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