The role of non-covalent interactions in 4-hydroxybenzylamine macrocyclisation: computational and synthetic evidence.

4-hydroxybenzylamine's intermolecular interactions and their possible influence on the course of 4-hydroxybenzylamine's reaction with formaldehyde are analysed in this article. Computational calculations established that 4-hydroxybenzylamine forms dimers in solution by O-H⋯N hydrogen bonds; such dimers are stabilised by π-stacking interactions. These cyclic dimers' formation led to obtaining a 12-atom azacyclophane through 4-hydroxybenzylamine's reaction with formaldehyde.