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Monosodium acetylide
View on Wikipedia | |
| Names | |
|---|---|
| IUPAC name
Ethynylsodium
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.012.645 |
| EC Number |
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| 174471 | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C2HNa | |
| Molar mass | 48.020 g·mol−1 |
| Appearance | white solid |
| Density | 1.352 g/cm3 |
| hydrolyzes | |
| Hazards | |
| GHS labelling:[1] | |
 
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| Danger | |
| H261, H314 | |
| P231+P232, P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Monosodium acetylide, also known as sodium hydrogen acetylide, is an organosodium compound with the formula NaC≡CH. It is a sodium salt of acetylene, consisting of sodium cations (Na+) and hydrogen acetylide anions (−C≡CH).[contradictory] It is a derived from acetylene by deprotonation using a sodium base, typically sodium amide.[2]
- HC≡CH + NaNH2 → NaC≡CH + NH3
This compound, a white solid, has been characterized by neutron diffraction, which revealed an Na-C bond[clarification needed] and a C≡C bond of 127 pm, which is longer than the C≡C bond length in acetylene itself (120.4 pm).[3]
Monosodium acetylide can be used as a strong nucleophile in organic synthesis.[2] However, it has largely been displaced in this application by monolithium acetylide, which can be prepared more easily.[4]
Monosodium acetylide hydrolizes in contact with water, producing sodium hydroxide and acetylene.
- NaC≡CH + H2O → HC≡CH + NaOH
Monosodium acetylide is used in the Nef synthesis.
References
[edit]- ^ "Sodium acetylide". pubchem.ncbi.nlm.nih.gov. Retrieved 3 September 2023.
- ^ a b K. N. Campbell, B. K. Campbell (1950). "n-Butylacetylene". Organic Syntheses. 30: 15. doi:10.15227/orgsyn.030.0015.
- ^ Atoji, Masao (1972). "Neutron Structure Determination of Monosodium Acetylide, NaC2H, at 293 and 5K". The Journal of Chemical Physics. 56 (10): 4947–4951. Bibcode:1972JChPh..56.4947A. doi:10.1063/1.1676972.
- ^ M. M. Midland; J. I. McLoughlin; R. T. Werley Jr. (1990). "Preparation and Use of Lithium Acetylide: 1-Methyl-2-Ethynyl-endo-3,3-Dimethyl-2-Norbornanol". Organic Syntheses. 68: 14. doi:10.15227/orgsyn.068.0014.