Acetylide
Acetylide, also known as ethynide, dicarbide, and percarbide, is an ion. Its chemical formula is C2−
2. It is made by deprotonation of acetylene. Some are known as carbides. Copper(I) acetylide is an example.
In organic chemistry
In organic chemistry, acetylide means the functional group –C≡C−
. This group is made by deprotonation of a terminal alkyne, –C≡CH.[1] Alkynes are more acidic than alkanes or alkenes. This means acetylides can be made with strong but common bases like sodium amide.[2]
Safety
Some acetylides (chemical compounds that contain acetylide ions) are explosive.[3][4]
Acetylide Media
Portion of the structure of the polymer copper(I) phenylacetylide Cu+
[−
C≡C–C
6H
5].
Reaction of ethyl propiolate with n-butyllithium to form the lithium acetylide.
Structure of sodium acetylide [Na+
]
2[−
C≡C−
]. Color code: gray = C, blue = Na.
Structure and unit cell of potassium acetylide [K+
]
2[−
C≡C−
].
Structure of the cluster formed from PhC≡CLi complexed to N,N,N′,N′-tetramethyl-1,6-diaminohexane (methylene groups omitted for clarity). Color key: turquoise = Li, blue = N.
Sources
- ↑ International Union of Pure and Applied Chemistry. "acetylide". Compendium of Chemical Terminology Internet edition.
- ↑ John C. McMurray. Organic Chemistry: A Tenth Edition (2023-09-20). Houston, TX: OpenStax.
- ↑ Silver acetylide - Knowledge and References (in en-US). Taylor & Francis. Retrieved 2025-09-20.
- ↑ Acetylide - an overview | ScienceDirect Topics. www.sciencedirect.com. Retrieved 2025-09-20.