Strong intermolecular interactions between functional groups and their effect on the physical properties of organic compounds

Comparative analysis of a series of organic compounds containing various functional group in their molecules was performed. The groups are potential sites of strong intermolecular interaction; effect of the interaction on the structure-sensitive parameters such as boiling point, melting point, and molecular packing factors was considered. The compared series are representative samplings from ca. 5000 compounds; they include organic compounds belonging to 14 classes with oxygen-, nitrogen- and halogen-containing functional groups. The analysis showed that the systems of intermolecular interactions exert a decisive effect on the properties of the compounds. An additional factor, often masking the main one, is the molecular shape, in particular, position of the center of intermolecular interactions in the molecule (in the middle or at the end). By the shape is meant a set of conformational states in complex organic molecules, determined, in turn, by the set of rotation barriers of separate atomic groups.