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Organic Chemistry Text Book (CHEM 3401 and 3402)

3.2 Acidity Constant

You are no doubt aware that some acids are stronger than others. The relative acidity of different compounds or functional groups – in other words, their relative capacity to donate a proton to a common base under identical conditions – is quantified by a number called the acidity constant, abbreviated Ka. The common base chosen for comparison is water.

pKa = -log Ka Ka = 10-pKa

The use of pKa values allows us to express the relative acidity of common compounds and functional groups on a numerical scale of about –10 (for a very strong acid) to 50 (for a compound that is not acidic at all). The lower the pKa value, the stronger the acid.

The ionizable (proton donating or accepting) functional groups relevant to biological organic chemistry generally have pKa values ranging from about 5 to about 20. The most important of these are summarized below, with very rough pKa values for the conjugate acid forms. More acidic groups with pKa values near zero are also included for reference.