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 Trimethylsilylacetylene is the organosilicon compound with the formula . A colorless liquid, "tms acetylene", as it is also called, is used as a source of "HC2−" in organic synthesis. Use Trimethylsilylacetylene is used in Sonogashira coupling ...

. Although samples explode above 80 °C, diiodoacetylene is the most readily handled of the dihaloacetylenes.

Dichloroacetylene Dichloroacetylene (DCA) is an organochlorine compound with the formula C2Cl2. It is a colorless, explosive liquid that has a sweet and "disagreeable" odor. Production Dichloroacetylene was first synthesized in 1930. Ether solutions of dichloroac ...

, for example, is more volatile and more explosive. As confirmed by

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...

, diiodoacetylene is linear. It is however a shock, heat and friction sensitive compound. Like other haloalkynes, diiodoacetylene is a strong

halogen bond A halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. Like a hydrogen bo ...

donor.{{cite journal , last1 = Cavallo , first1 = G. , last2 = Metrangolo , first2 = P. , last3 = Milani , first3 = R. , last4 = Pilati , first4 = T. , last5 = Priimagi , first5 = A. , last6 = Resnati , first6 = G. , last7 = Terraneo , first7 = G. , title = The Halogen Bond , journal=

Chem. Rev. ''Chemical Reviews'' is peer-reviewed scientific journal published twice per month by the American Chemical Society. It publishes review articles on all aspects of chemistry. It was established in 1924 by William Albert Noyes (University of Illinoi ...

, date = 2016 , volume = 116 , issue = 4 , pages = 2478–2601 , doi = 10.1021/acs.chemrev.5b00484 , pmid = 26812185 , pmc = 4768247

References

Inorganic carbon compounds Organoiodides Dihaloacetylenes