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
Appearance	white solid
Density	3.43 g/cm3
	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 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

^ Perkins, Catherine; Libri, Stefano; Adams, Harry; Brammer, Lee (2012). "Diiodoacetylene: Compact, Strong Ditopic Halogen Bond Donor". CrystEngComm. 14 (9): 3033. doi:10.1039/c2ce00029f.
^ 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.
^ 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..
^ 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.

[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.

[alkyne-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.

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