Chemistry:Monosodium acetylide

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Monosodium acetylide
NaC2H.svg
Names
IUPAC name
Ethynylsodium
Other names
sodium acetylide, sodium ethynide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 213-908-9
174471
Properties
C2HNa
Molar mass 48.020 g·mol−1
Appearance white solid
Density 1.352 g/cm3
hydrolysis
Hazards
GHS pictograms GHS02: FlammableGHS05: Corrosive
GHS Signal word Danger
H261, H314
P231+232, P260, P264, P280, P301+330+331, P302+361+354Script error: No such module "Preview warning".Category:GHS errors, P304+340, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P321, P363, P370+378, P402+404, 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 is an organosodium compound with the formula NaC2H. It is a derived from acetylene by deprotonation using a sodium base, typically sodium amide.[2] This compound, a white solid, has been characterized by neutron diffraction, which revealed an Na-C bond and an elongated C≡C bond of 1.27 Å, which is longer than the C≡C bond length in acetylene itself (1.204 Å).[3] As a reagent, monosodium acetylide has been largely displaced by monolithium acetylide, which can be prepared more easily.[4]

References

  1. "Sodium acetylide" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/2733336#section=Safety-and-Hazards. 
  2. 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. doi:10.1063/1.1676972. Bibcode1972JChPh..56.4947A. 
  4. 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.