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 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 and a C≡C bond of 127 pm, which is longer than the C≡C bond length in acetylene itself (120.4 pm).[3] As a reagent, monosodium acetylide has been largely displaced 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

  1. ^ "Sodium acetylide". pubchem.ncbi.nlm.nih.gov. Retrieved 3 September 2023.
  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. Bibcode:1972JChPh..56.4947A. doi:10.1063/1.1676972.
  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.
Allikas: http://en.wikipedia.org/wiki/Sodium_acetylide
No tags for this post.