Diiodoacetylene Explained

Diiodoacetylene is the organoiodine compound with the formula C2I2. It is a white, volatile solid that dissolves in organic solvents. It is prepared by iodination of trimethylsilylacetylene.[1] Although samples explode above 80 °C, diiodoacetylene is the most readily handled of the dihaloacetylenes. Dichloroacetylene, for example, is more volatile and more explosive.[2] As confirmed by X-ray crystallography, diiodoacetylene is linear.[3] It is however a shock, heat and friction sensitive compound. Like other haloalkynes, diiodoacetylene is a strong halogen bond donor.[4]

References

  1. 10.1039/c2ce00029f. Diiodoacetylene: Compact, Strong Ditopic Halogen Bond Donor. 2012. Perkins. Catherine. Libri. Stefano. Adams. Harry. Brammer. Lee. CrystEngComm. 14. 9. 3033.
  2. Book: Modern Acetylene Chemistry . Stang, Peter J. . Diederich, François . Weinheim . VCH . 1995 . 9783527615261 . Functionalized Acetylenes in Organic Synthesis ‐ The Case of the 1‐Cyano‐ and the 1‐Halogenoacetylenes . Henning Hopf . Bernhard Witulski . 33–66 . 10.1002/9783527615278.ch02.
  3. 10.1107/S0567740872005400. The Crystal Structure of Diiodacetylene: An Example of Pseudosymmetry. 1972. Dunitz. J. D.. Gehrer. H.. Britton. D.. Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 28. 7. 1989–1994. .
  4. Cavallo . G. . Metrangolo . P. . Milani . R. . Pilati . T. . Priimagi . A. . Resnati . G. . Terraneo . G. . The Halogen Bond . . 2016 . 116 . 4 . 2478–2601 . 10.1021/acs.chemrev.5b00484 . 26812185 . 4768247 .

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