Adamanzane

Structure of [1⁴.2²]adz

Structure of Hexamethylenetetramine

Adamanzanes (abbreviated Adz) are compounds containing four nitrogen atoms linked by carbons (analogous to adamantane with nitrogen at the branched position). Often coordinated to a central ligand, the nitrogens occupy the vertices of a tetrahedron, 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, [1⁴.2²]adz is 1,3,6,8-tetraazatricyclo[4.4.1.13,8]-dodecane, a compound which contains four one-carbon chains and two two-carbon chains linking the nitrogens.^[1]

3⁶adamanzane 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⁻.^[2]

References

1. Yonggang He; et al. (2005). "Structure of Gas Phase Radical Cation of 1,3,6,8-Tetraazatricyclo[4.4.1.13,8] Dodecane Determined from Zero Kinetic Energy Photoelectron Spectroscopy" (PDF). J. Phys. Chem. A 109 (6). doi:10.1021/jp0444619.
2. Mikhail Y. Redko; et al. (2002). ""Inverse Sodium Hydride":  A Crystalline Salt that Contains H⁺ and Na⁻". J. Am. Chem. Soc. 124 (21): 5928–5929. doi:10.1021/ja025655+.