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.
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