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{{Chembox
{{Chembox
| Watchedfields = changed
| verifiedrevid = 395434227
| verifiedrevid = 431909367
| ImageFile = Silver acetylide.png
| ImageSize = 120px
| Name =
| ImageName = Wireframe model of silver acetylide
| ImageFile = Silver acetylide.png
| ImageSize = 120px
| ImageFile2 = Silver acetylide3.jpg
| PIN = Disilver acetylide
| ImageName = Wireframe model of silver acetylide
| ImageFile2 = Silver acetylide3.jpg
| SystematicName = Disilver(1+) ethyndiide
| PIN = Silver acetylide
| OtherNames = Argentous ethyndiide<br />
| SystematicName = Silver(I) ethynediide
Argentous percarbide<br />
| OtherNames = {{ubl|Silver percarbide|Silver carbide|Silver dicarbide|Argentous acetylide|Argentous ethynediide|Argentous percarbide|Argentous carbide|Argentous dicarbide}}
Silver(1+) dicarbon<br />
| IUPACName =
Silver ethynide<br />
Silver percarbide
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 7659-31-6
| SMILES = [Ag+].[Ag+].[C-]#[C-]
| CASNo = 7659-31-6
| SMILES = [Ag+].[Ag+].[C-]#[C-]
| InChI = 1S/C2.2Ag/c1-2;;/q-2;2*+1
| InChI = 1S/C2.2Ag/c1-2;;/q-2;2*+1
| InChIKey = FIDGMLJJLFFOEI-UHFFFAOYSA-N}}
| InChIKey = FIDGMLJJLFFOEI-UHFFFAOYSA-N}}
|Section2={{Chembox Properties
| Section2 = {{Chembox Properties
| Formula = {{chem2|Ag2C2}}
| C=2|Ag=2
| Appearance= gray or white solid
| C=2 | Ag=2
| Appearance= gray or white solid
| Density= 4.47 g/cm<sup>3</sup><ref>{{cite journal |last1=McCowan |first1=J. D. |title=Decomposition of silver acetylide |journal=Transactions of the Faraday Society |date=1963 |volume=59 |pages=1860–1864|doi=10.1039/tf9635901860}}</ref>
| Density=
| MeltingPt= 120 °C
| MeltingPtC= 120
| BoilingPt= decomposes
| BoilingPt= decomposes
| Solubility= insoluble
| Solubility= insoluble
}}
| VOD= 4000 m(s-1)
| Section3 = {{Chembox Hazards
}}
| MainHazards= highly sensitive primary explosive
|Section3={{Chembox Hazards
| NFPA-F = 3
| MainHazards= High Explosive, Toxic
| NFPA-H = 3
| FlashPt= flammable
| NFPA-R = 4
| Autoignition=
| FlashPtC = 77
}}
| AutoignitionPtC =
}}
| Section4 =
|Section5={{Chembox Thermochemistry
| DeltaHf = 357.6±5.0 kJ/mol<ref>{{cite journal |last1=Finch |first1=Arthur |last2=Gardner |first2=Peter J. |last3=Head |first3=Arthur J. |last4=Majdi |first4=Hassan S. |title=The standard enthalpy of formation of silver acetylide |journal=Thermochimica Acta |date=1991 |volume=180 |pages=325–330 |doi=10.1016/0040-6031(91)80402-5}}</ref>
}}
| Section6 =
}}
}}


'''Silver acetylide''' is an inorganic chemical compound with the formula Ag<sub>2</sub>C<sub>2</sub>, a [[metal acetylide]]. The name is derived from the way it is synthesized, and emphasizes that the compound can be regarded as a salt of the weak [[acid]], [[acetylene]]. Since acetylene is called "ethyne" in the modern [[IUPAC]] nomenclature, the name "silver ethynide" would be more appropriate. In either case, the name makes it clear that the anion consists of two [[carbon]] atoms linked by a [[triple bond]]. The less specific alternative "silver carbide" is not used, although the analogous calcium compound CaC<sub>2</sub> is called [[calcium carbide]]. Silver acetylide is a heat- and shock-sensitive high [[explosive]] with the unusual property that on ignition it does not evolve any gas:
'''Silver acetylide''' is an [[inorganic chemical compound]] with the formula {{chem2|Ag2C2|auto=1}}, a [[metal acetylide]]. The compound can be regarded as a [[silver]] [[salt (chemistry)|salt]] of the weak [[acid]], [[acetylene]]. The salt's [[anion]] consists of two [[carbon]] atoms linked by a [[triple bond]], thus, its structure is {{chem2|[Ag+]2[−C\tC−]}}. The alternate name "silver carbide" is rarely used, although the analogous calcium compound {{chem2|CaC2}} is called [[calcium carbide]]. Silver acetylide is a primary [[explosive]].

:{{chem|Ag|2|C|2}} (s) → 2 Ag (s) + 2 C (s)

The detonation velocity of silver acetylide is 3460&nbsp;m/s.<ref>https://www.powerlabs.org/chemlabs/acetylide.htm</ref>


== Synthesis ==
== Synthesis ==


Silver acetylide can be produced by passing [[acetylene]] gas through a solution of [[silver nitrate]]:<ref>{{cite journal|author = G.-C. Guo, Q.-G. Wang, G.-D. Zhou, T. C. W. Mak|title =Synthesis and characterization of Ag<sub>2</sub>C<sub>2</sub>·2AgClO<sub>4</sub>·2H<sub>2</sub>O: a novel layer-type structure with the acetylide dianion functioning in a <sub>6</sub>-η<sup>1</sup>,η<sup>1</sup>:η<sup>2</sup>,η<sup>2</sup>:η<sup>2</sup>,η<sup>2</sup> bonding mode inside an octahedral silver cage|journal= [[Chem. Commun.]]|issue = 3|year= 1998|pages= 339–340|doi=10.1039/a708439k}}</ref>
Silver acetylide can be produced by passing [[acetylene]] gas through a solution of [[silver nitrate]]:<ref>{{cite journal|author1=G.-C. Guo |author2=Q.-G. Wang |author3=G.-D. Zhou |author4=T. C. W. Mak |title =Synthesis and characterization of Ag<sub>2</sub>C<sub>2</sub>·2AgClO<sub>4</sub>·2H<sub>2</sub>O: a novel layer-type structure with the acetylide dianion functioning in a <sub>6</sub>-η<sup>1</sup>,η<sup>1</sup>:η<sup>2</sup>,η<sup>2</sup>:η<sup>2</sup>,η<sup>2</sup> bonding mode inside an octahedral silver cage|journal= [[Chem. Commun.]]|issue = 3|year= 1998|pages= 339–340|doi=10.1039/a708439k}}</ref>


:2 {{chem|AgNO|3}} + {{chem|C|2|H|2}} (g) → {{chem|Ag|2|C|2}} (s) + 2 {{chem|HNO|3}} (aq)
:{{chem2|2 AgNO3(aq) + C2H2(g) → Ag2C2(s) + 2 [[Nitric acid|HNO3]](aq)}}


The reaction product is a greyish to white precipitate. This is the same synthesis from [[Marcellin Berthelot|Berthelot]] in which he first found silver acetylide in 1866.<ref>{{cite journal
The reaction product is a greyish to white precipitate. This is the same synthesis from [[Marcellin Berthelot|Berthelot]] in which he first found silver acetylide in 1866.<ref>{{cite journal
| author = [[M. P. Berthelot]]
| author = M. P. Berthelot
| title =Ueber eine neue Klasse zusammengesetzter metallhaltiger Radicale (A new class of combined metallic radicals)
| title =Ueber eine neue Klasse zusammengesetzter metallhaltiger Radicale (A new class of combined metallic radicals)
| journal= [[Annalen der Chemie]]
| journal= [[Annalen der Chemie]]
Line 54: Line 58:
| issue = 2
| issue = 2
| doi = 10.1002/jlac.18661380215
| doi = 10.1002/jlac.18661380215
| author-link =M. P. Berthelot
| url =https://zenodo.org/record/1427253
}}</ref>
}}</ref>

The double salt is formed in acidic or neutral silver nitrate solutions. Performing the synthesis in [[Base (chemistry)|basic]] [[ammonia]] solution does not allow the [[double salt]] to form, producing pure silver acetylide. To properly form the double salt, acetylene gas is passed through dilute silver nitrate and nitric acid solution. Instead of the conventional synthesis of passing acetylene gas through silver nitrate solution, a purer and whiter precipitate can be formed by passing acetylene gas through [[acetone]] and adding the acetylene solution drop-wise to a dilute silver nitrate and nitric acid solution. The reaction was performed at ambient room temperature.


Silver acetylide can be formed on the surface of silver or high-silver alloys, e.g. in pipes used for transport of acetylene, if silver brazing was used in their joints.
Silver acetylide can be formed on the surface of silver or high-silver alloys, e.g. in pipes used for transport of acetylene, if silver brazing was used in their joints.

== Explosive character ==
Pure silver acetylide is a heat- and shock-sensitive [[primary explosive]]. Silver acetylide decomposes through the reaction:

:{{chem2|Ag2C2(s) → 2 Ag(s) + 2 C(s)}}

The [[Velocity of detonation|detonation velocity]] of the silver acetylide-silver nitrate double salt is 1980&nbsp;m/s, while that of pure silver acetylide is 1200&nbsp;m/s.<ref>{{Cite book|last1=Matyáš|first1=Robert|title=Primary Explosives|last2=Pachman|first2=Jiří|date=2013|publisher=Springer Berlin Heidelberg|isbn=9783642284359|location=Berlin, Heidelberg|language=en|doi=10.1007/978-3-642-28436-6|s2cid=199492549}}</ref>


== Solubility ==
== Solubility ==
Silver acetylide is not soluble in water and there are no known solvents for it other than those that would decompose it.
Silver acetylide is not soluble in water and is not appreciably soluble in any other solvent.


== References ==
== References ==
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{{Silver compounds}}
{{Silver compounds}}
{{Carbides}}


[[Category:Silver compounds]]
[[Category:Organosilver compounds]]
[[Category:Acetylides]]
[[Category:Acetylides]]
[[Category:Explosive chemicals]]
[[Category:Explosive chemicals]]
[[Category:Carbides]]

[[ar:أسيتيليد الفضة]]
[[de:Silberacetylid]]
[[es:Acetiluro de plata]]
[[fr:Acétylure d'argent]]
[[it:Carburo di argento]]
[[nl:Zilveracetylide]]
[[pl:Acetylenek srebra]]
[[pt:Acetileto de prata]]
[[ru:Ацетиленид серебра]]