This work reports detailed structural
characterization of 13 new
multicomponent solid forms of p-aminosalicylic acid
(PAS) with various pyridine based compounds that include eight cocrystals,
two salt cocrystals, two salts, and a salt hydrate. The structural
chemistry of all solids of PAS with pyridine based coformers including
those previously reported were analyzed in terms of PAS–coformer
dimer or PAS–coformer–PAS trimer based on the carboxylic
acid···pyridine synthon. The robustness of the carboxylic
acid···pyridine synthon in the construction of a variety
of multicomponent structures, the influence of solution composition
and solvent in dictating the outcome of the crystallization event,
and the applicability of the ΔpK
a rule on a set of 32 PAS based multicomponent solids are also discussed.