Misplaced Pages

Diiodoacetylene

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Diiodoacetylene
Names
Preferred IUPAC name Diiodoethyne
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2I2/c3-1-2-4Key: XANKMCMFEJCODV-UHFFFAOYSA-N
SMILES
  • C(#CI)I
Properties
Chemical formula C2I2
Appearance white solid
Density 3.43 g/cm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. Although samples explode above 80 °C, diiodoacetylene is the most readily handled of the dihaloacetylenes. Dichloroacetylene, for example, is more volatile and more explosive. As confirmed by X-ray crystallography, diiodoacetylene is linear. It is however a shock, heat and friction sensitive compound. Like other haloalkynes, diiodoacetylene is a strong halogen bond donor.

References

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