Isolation of hydrazine oxidation products via halogen bonding: C–I bond scission and crystal polymorphism†
Abstract
Reaction of methylhydrazine with 1,3- and 1,4-diiodotetrafluorobenzene produced cocrystals with the oxidation product sym-hexahydro-1,4-dimethyltetrazine. In contrast, reaction of 1,1-dimethylhydrazine with 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene, as well as 1,3,5-triiodotrifluorobenzene, yielded cocrystals with tetramethylammonium iodide (NMe4I), via C–I bond scission. For each of the NMe4I cocrystals, different polymoprhs or cocrystal stoichiometries were obtained via the C–I bond scission route, than were obtained by direct reaction of the halobenzene and NMe4I by standard solution techniques.
- This article is part of the themed collection: Supramolecular & Polymorphism