In the publication, a number of intermolecular factors associated with hydrogen bonded complexes were described. Those were discussed in the light of substituent electronic effect and steric hindrance, electron intra- and intermolecular repulsion and conformational equilibrium. The intermolecular forces that might be used in the design of molecular aggregates were discussed in the light of the hydrogen bonding energy, their order of appearance and the existence of secondary interactions. Also, the competition between intramolecular hydrogen bonding that stabilizes the respective rotamer and the intermolecular hydrogen bonding leading to the association of molecules were exemplified. Finally, the examples of molecules in which all effects are present and discussed.
Keywords: Hydrogen bonding, steric effects, substituent effect, conformational equilibrium, supramolecular chemistry.