Diiodoacetylene

Diiodoacetylene

Names
Preferred IUPAC name Diiodoethyne
Identifiers
CAS Number	624-74-8
3D model (JSmol)	Interactive image
ChemSpider	55116
PubChem CID	61170
CompTox Dashboard (EPA)	DTXSID20211459
InChI InChI=1S/C2I2/c3-1-2-4 Key: XANKMCMFEJCODV-UHFFFAOYSA-N
SMILES C(#CI)I
Properties
Chemical formula	C2I2
Molar mass	277.831 g·mol−1
Appearance	white solid
Density	3.43 g/cm3
Related compounds
Related compounds	Acetylene Difluoroacetylene Dichloroacetylene Dibromoacetylene Tetraiodoethylene Tetraiodomethane Hexaiodoethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diiodoacetylene is the organoiodine compound with the formula C ₂ I ₂. 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] with the structure I−C≡C−I. It is however a shock, heat and friction sensitive compound. Like other haloalkynes, diiodoacetylene is a strong halogen bond donor. ^[4]

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.