User:Korbnep/Hexamine

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Synthesis, structure, reactivity
Hexamethylenetetramine is prepared by the reaction of formaldehyde and ammonia. The reaction can be conducted in gas-phase and in solution.

The molecule has a symmetric tetrahedral cage-like structure, similar to adamantane, whose four "corners" are nitrogen atoms and "edges" are methylene bridges. Although the molecular shape defines a cage, no void space is available at the interior for binding other atoms or molecules, unlike crown ethers or larger cryptand structures.

The molecule behaves like an amine base, undergoing protonation and N-alkylation.

When reacted with nitric acid, hexamine forms the explosive RDX (known chemically as cyclotrimethylenetrinitramine). It can also be reacted with hydrogen peroxide, with a catalyst of citric acid or dilute sulfuric acid, to form hexamethylene triperoxide diamine.