Influence of sulfur groups on carboxylic acid strengths
2018
Boschmann, Erwin | Miller, Roger D.
The relative acid strength for a series of monocarboxylic acids of the general formula RX(CH2)nCOOH and related dicarboxylic acids of the general formula HOOC(CH2)nX(CH2)nCOOH, where R = Ph or Me, X = CH2, S, SO, or SO2; and n = 1 or 2 as appropriate; have been studied as a function of X. It is found that sulfur containing acids have lower pKa values than the corresponding carbon analogues, that the pKa is highest for the thioacids and lowest for the sulfonyl acids, that the pKas increase as n increases, and that for the dicarboxylic acid systems only the thio members show a significant reduction in pKa (2) – pKa (1) differences upon changing n from 1 to 2.
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