Adamanzanes (abbreviated ''Adz'') are compounds containing four

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

atoms linked by

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

s (analogous to

adamantane Adamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the mo ...

with nitrogen at the branched position). Often coordinated to a central ligand, the nitrogens occupy the vertices of a

tetrahedron In geometry, a tetrahedron (: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular Face (geometry), faces, six straight Edge (geometry), edges, and four vertex (geometry), vertices. The tet ...

, with potentially four faces and six edges, with the carbon chains running approximately along the edges. They can have a "bowl" or "cage" structure, with varying lengths or omission of the carbon chains. In the nomenclature of Springborg ''et al.'' (1996) these can be described according to the number of chains of specified length: thus, for example, ⁴.2²damanzane is 1,3,6,8-tetraazatricyclo .4.1.1^3,8odecane, a compound which contains four one-carbon chains and two two-carbon chains linking the nitrogen atoms. ⁶damanzane has found a special use in the preparation of " inverse sodium hydride", a compound in which Na⁻ and H⁺ ions coexist, due to the ability of the adamanzane to encapsulate the H⁺ and render it kinetically inert to react with the Na⁻.{{cite journal, title="Inverse Sodium Hydride": A Crystalline Salt that Contains H⁺ and Na⁻, author=Mikhail Y. Redko, journal=J. Am. Chem. Soc., year=2002, volume=124, issue=21, pages=5928–5929, doi=10.1021/ja025655+, display-authors=etal, pmid=12022811

References

Nitrogen heterocycles Adamantane-like molecules Heterocyclic compounds with 3 rings