A comparison of the intramolecular and intermolecular hydrogen bonding of N,N′-ethylenebis(aminobenzylidene) in the solid state with its salen analogue

The crystal structure of H₂amben has been elucidated for the first time. The close NH?N contact between neighbouring molecules supports strongly the notion that intermolecular hydrogen bonding exists within the crystal lattice, creating a series of molecular chains, which are crosslinked in a three-dimensional array. This intermolecular bonding is suggested to account for the anomalously high melting point of H₂amben (176-178 °C) compared to its H₂salen counterpart (126-128 °C). Although strong intramolecular forces are present in both ligands, H₂salen contains no intermolecular hydrogen bonds.