The concept of the so-called "supramolecular synthon" has been employed to construct chiral and centrosymmetric cocrystals with predictable short-range order. The reactants included nicotinamide, mandelic acid and ibuprofen. In order to maximize the efficiency of cocrystal synthesis, the solids were constructed using the liquid-assisted grinding approach. The predictability of the cocrystal architecture was further employed to study in detail the effects of chirality upon physical properties of the synthesized materials, especially the melting point. The combined results of crystallographic and thermochemical studies enable, at least partially, the rationalisation of cocrystal thermal behaviour with respect to the corresponding cocrystal formers.