Monosodium acetylide

Monosodium acetylide
Names
IUPAC name
Ethynylsodium
Other names
  • Sodium hydrogen acetylide
  • Sodium hydrogen ethynide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.645
EC Number
  • 213-908-9
174471
  • InChI=1S/C2H.Na/c1-2;/h1H;/q-1;+1
    Key: SFDZETWZUCDYMD-UHFFFAOYSA-N
  • C#[C-].[Na+]
Properties
C2HNa
Molar mass 48.020 g·mol−1
Appearance white solid
Density 1.352 g/cm3
hydrolyzes
Hazards
GHS labelling:[1]
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).
Infobox references

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). It is 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 a C≡C bond of 127 pm, which is longer than the C≡C bond length in acetylene itself (120.4 pm). The negative formal charge is essentially localized on one of the carbon atoms.[3] Millimeter spectroscopy yielded Na−C and C≡C bond lengths of 222.1 pm and 121.7 pm, respectively. The C−H bond length is assumed to be 106 pm.[4]

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.[5]

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.

Monosodium acetylide is theorized to exist in the outer envelopes of carbon stars such as IRC +10216, where it could be formed by the reaction between sodium or sodium cations and ethynyl radicals or acetylene cations (HCCH+), the latter two produced by photodissociation.[6]

References

  1. ^ "Sodium acetylide". pubchem.ncbi.nlm.nih.gov. Retrieved 3 September 2023.
  2. ^ a b K. N. Campbell, B. K. Campbell (1950). "n-Butylacetylene". Organic Syntheses. 30: 15. doi:10.15227/orgsyn.030.0015.
  3. ^ 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.
  4. ^ Grotjahn, Douglas B.; Apponi, Aldo J.; Brewster, Matthew A.; Xin, Ju; Ziurys, Lucy M. (1998-10-16). "Structures of Solvent-Free, Monomeric LiCCH, NaCCH, and KCCH". Angewandte Chemie International Edition. 37 (19): 2678–2681. doi:10.1002/(SICI)1521-3773(19981016)37:19<2678::AID-ANIE2678>3.0.CO;2-6. ISSN 1433-7851. Retrieved 2026-05-06.
  5. ^ 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.
  6. ^ Li, B. Z.; Ziurys, L. M. (1997-06-20). "Laboratory Detection and Submillimeter Spectrum of NaCCH (x̃ 1Σ)". The Astrophysical Journal. 482 (2): L215–L217. doi:10.1086/310707. Retrieved 2026-05-06.
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