Acetylide
chemical compound in which one or both hydrogen atoms of acetylene (ethyne) was replaced by a metal or other cationic group; also analogous compound derived from terminal acetylenes

In chemistry, an acetylide is a compound that can be viewed as the result of replacing one or both hydrogen atoms of acetylene (ethyne) HC≡CH by metallic or other cations. Calcium carbide is an important industrial compound, which has long been used to produce acetylene for welding and illumination. It is also a major precursor to vinyl chloride. Other acetylides are reagents in organic synthesis.
Nomenclature
The term acetylide is used loosely. It applies to an acetylene RC≡CM, where R = H or a side chain that is usually organic. The nomenclature can be ambiguous with regards to the distinction between compounds of the types MC2R and M2C2. When both hydrogens of acetylene are replaced by metals, the compound can also be called carbide, e.g., calcium carbide Ca2+[−C≡C−], which is calcium acetylide. When only one hydrogen atom is replaced, the anion may be called hydrogen acetylide or the prefix mono- may be attached to the metal, as in monosodium acetylide or sodium hydrogen acetylide, Na+[−C≡CH]. Metal acetylide may be described as salts, but that description rarely comports with crystallographic analysis.
“Acetylide” enters the record as chemical compound in which one or both hydrogen atoms of acetylene (ethyne) was replaced by a metal or other cationic group; also analogous compound derived from terminal acetylenes. Crown Archives preserves that source wording while asking what Acetylide, chemical and compound can confirm, complicate or overturn.
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