Adamanzane

Adamanzanes (abbreviated Adz) are compounds containing four nitrogen atoms linked by carbons (analogous to adamantane with nitrogen at the branched position).

Structure of [14.22]adamanzane
Structure of hexamethylenetetramine

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]adamanzane 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 nitrogen atoms.[1]

[36]Adamanzane 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): 959–961. Bibcode:2005JPCA..109..959H. doi:10.1021/jp0444619. PMID 16833400. Archived from the original (PDF) on 2012-01-03.
  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+. PMID 12022811.
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