Acetylide
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| Identifiers | |
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29075-95-4 (HC≡C−) 34846-56-5 (C22−) |
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| 3D model (Jmol) | Interactive image |
| ChemSpider |
11316391 (HC≡C−) 6113 (C22−) 
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| Properties | |
| HC− 2 |
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| Molar mass | 25.03 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Acetylide is a carbanion with the chemical formula HC≡C−. The classification includes saline carbides and organometallic compounds of terminal alkynes and acetylene. Substituted acetylides, which have the general structure RC≡C− (where R is an organic side chain), are useful reagents in organic synthesis.
The double or single deprotonation product of acetylene is often referred to as an acetylide anion of the formula C2−
2 or HC−
2 respectively. The doubly deprotonated product has a closed shell ground state of 1Σg+, making it isoelectronic to a neutral molecule N2, This chemical structure affords it some stability in the gas phase but makes it reactive to strong bases in the liquid phase (see acetylene bonding).
Although acetylides are often described as anions in salts, acetylides are more accurately described as complex structures of an anion strongly bonded to a metal cation. Nevertheless, the anion names are used for salt-like materials such as alkali metal acetylides, copper acetylide (Cu2C2), lithium hydrogenacetylide (LiC2H), and silver methylacetylide (AgCH3C2). Some metal acetylides are traditionally called carbides. For example, lithium carbide and calcium carbide are really derivatives of C2−
2.
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