Azide



Azide is the anion with the formula N3−. It is the valence bond theory, azide can be described by several resonance structures, an important one being N−=N+=N−.

Inorganic azides

Azide forms both covalent and ionic compounds with metals. trimethylsilylazide, which is sometimes used as an anhydrous source of N3−.

Azides in biochemistry

The azide anion is toxic, inhibiting the function of mutagenesis.

Organic azides

Organic azides engage in useful Curtius rearrangement or for example in the synthesis of γ-imino-β-enamino esters [3] [4].

In the zidovudine (AZT).

Another azide regular is tosyl azide here in reaction with norbornadiene in a nitrogen insertion reaction [5]:

Safety

  • Sodium azide is toxic (LD50 oral (rats) = 27 mg/kg) and can be absorbed through the skin.
  • lead azide are very explosive when heated or shaken.
  • Sodium azide decomposes explosively upon heating to above 275 °C.
  • Sodium azide reacts vigorously with lead.
  • In reaction with water or Brønsted acids the highly toxic and explosive hydrogen azide is released.
  • It has been reported that sodium azide and polymer-bound azide reagents react with chloroform to form di- and triazidomethane resp., which are both unstable in high concentrations in solution. Various devastating explosions were reported while reaction mixtures were being concentrated on a rotary evaporator. The hazards of diazidomethane (and triazidomethane) have been well documented by A. Hassner et al. [6].
  • Heavy-metal azides that are highly explosive under pressure or shock are formed when solutions of sodium azide or HN3 vapors come into contact with heavy metals or their salts. Heavy-metal azides can accumulate under certain circumstances, for example, in metal pipelines and on the metal components of diverse equipment (cytochrome c oxidase (COX) inhibitors).
  • Solid iodoazide is explosive and should not be prepared in the absence of solvent.[7].

References

  1. ^ Review: S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320-5374; Angew. Chem. Int. Ed. 2005, 44, 5188-5240.
  2. ^ Tornieporth-Oetting, I. C.; Klapoetke, T. M. "Covalent Inorganic Azides" Angewandte Chemie, International Edition in English (1995), volume 34, pages 511-20. AN 1995:483017
  3. ^ An efficient synthesis of γ-imino- and γ-amino-β-enamino esters Mangelinckx, S.; Van Vooren, P.; De Clerck, D.; Fülöp, F.; De Kimpea, N. Arkivoc JC-1560E 2005 Online Article
  4. ^ Reaction conditions: a) trans isomers
  5. ^ A Facile Synthesis of a Polyhydroxylated 2-Azabicyclo[3.2.1]octane Damon D. Reed and Stephen C. Bergmeier J. Org. Chem.; 2007; 72(3) pp 1024 - 1026; (Note) doi:10.1021/jo0619231
  6. ^ A. Hassner et al., Angew. Chem. Int. Ed. Engl., 25, 479 (1986), J. Org. Chem., 55, 2304 (1990).
  7. ^ L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem. 2003, 68, 9453 – 9455.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Azide". A list of authors is available in Wikipedia.