Halogens On, H-Bonds Off—Insights into Structure Control of Dihalogenated Imidazole Derivatives

Halogen bonds play an important role in the targeted generation of solid-state structures, with polyhalogenated compounds enabling the simultaneous formation of various interactions. In this manuscript, we investigate the interactions of dihalogenated compounds in the solid state. Unlike investigated in previous studies, the introduction of protective groups in these compounds prevents the formation of dominant hydrogen bonds. The structures of diiodo imidazole derivatives are compared with the analogous dibromo compounds. A total of four different protective groups (two benzylic and two oxycarbonyl protective groups) are introduced and the respective compounds are characterized by X-ray crystallography. The significance of the protective groups for the solid-state structure can be distinguished on the basis of the additional donor atoms and functional groups. It can be seen that the iodo compounds in particular are capable of forming halogen bonds and that additional structural motifs can be generated by suitable protective groups.