Molecular Assemblies from Imidazolyl-Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Karim Bouchmella (1) , Bruno Boury (1) , Sylvain G. Dutremez (1) , A. van Der Lee (2)

1 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 IEM - Institut Européen des membranes

1-(3-Iodopropargyl)imidazole and 1-(2,3,3-triiodoallyl)imidazole self-assemble to give polymeric chains as a result of N...I halogen bonding. However, these interactions are not sufficiently strong to compete with hydrogen bonding. N-H...O and N-H...N interactions govern the molecular arrangement in the 1:1 cocrystal of 1-(2,3,3-triiodoallyl)imidazole and morpholinium iodide.

Mots clés: crystal engineering · donor–acceptor systems · halogen bonding · hydrogen bonds · self-assembly

Domaines: Chimie organique

Karim Bouchmella, Bruno Boury, Sylvain G. Dutremez, A. van Der Lee. Molecular Assemblies from Imidazolyl-Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding. Chemistry - A European Journal, 2007, 13 (21), pp.6130. ⟨10.1002/chem.200601508⟩. ⟨hal-00189513⟩