pKa values in organic chemistry – Making maximum use of the available data.

Graphical abstract Highlights • p K a values depend strongly on solvent's acid-base properties and polarity. • Relative p K a values (Δp K a) can often be cross-used between aprotic solvents. • Ion pairing or hydrogen-bonded complexes are important in many solvents. Abstract Acids and bases are ubiquitous. Sometimes, it is essential to know the accurate strength (p K a values) of the acids/bases to work with, but sometimes just acidity/basicity order is enough. We often receive requests to measure p K a values of different substances in different solvents for answering questions like "what acids can be used to protonate this substance" or "what base is able to deprotonate that compound?" Such questions can, in fact, often be answered using published p K a data in different solvents. This digest/tutorial will give an overview of how to make efficient use of the existing p K a data. [ABSTRACT FROM AUTHOR]