A structural study of the intermolecular interactions of tyramine in the solid state and in solution

The nature of the interactions between tyramine units was investigated in the solid state and in solution. Crystals of tyramine in its free base form were analyzed by Fourier transform infrared (FT-IR) spectroscopy and single-crystal X-ray diffraction (XRD). The crystal structure shows a linear molecular organization held together by “head-to-tail” intermolecular hydrogen bonds between the amino groups and the phenolic hydroxyl groups. These chains are arranged in double layers that can geometrically favor the formation of templates in solution, which may facilitate macrocyclization reactions to form azacyclophane-type compounds. Computational calculations using the PM6-DH+ method and electrospray ionization mass spectrometry (ESI-HRMS) reveal that the formation of a hydrogen-bonded tyramine dimer is favored in solution.

► The interactions between tyramine units were studied in the solid state and in solution.
► The X-ray structure of tyramine was reported for the first time.
► The crystal structure is stabilized by intermolecular OH--N hydrogen bonds.
► Semiempirical calculations showed the formation of tyramine templates in solution.