Monosodium acetylide explained

Monosodium acetylide is an organosodium compound with the formula . It is a sodium salt of acetylene, consisting of sodium cations and hydrogen acetylide anions . It is a derived from acetylene by deprotonation using a sodium base, typically sodium amide.[1]

This compound, a white solid, has been characterized by neutron diffraction, which revealed an Na-C bond and a bond of 127 pm, which is longer than the bond length in acetylene itself (120.4 pm).[2] As a reagent, monosodium acetylide has been largely displaced by monolithium acetylide, which can be prepared more easily.[3]

Monosodium acetylide hydrolizes in contact with water, producing sodium hydroxide and acetylene.

References

  1. 10.15227/orgsyn.030.0015 . n-Butylacetylene . Organic Syntheses . 1950 . 30 . 15. K. N. Campbell, B. K. Campbell.
  2. 10.1063/1.1676972 . Neutron Structure Determination of Monosodium Acetylide, NaC2H, at 293 and 5K . 1972 . Atoji . Masao . The Journal of Chemical Physics . 56 . 10 . 4947–4951 . 1972JChPh..56.4947A.
  3. 10.15227/orgsyn.068.0014 . Preparation and Use of Lithium Acetylide: 1-Methyl-2-Ethynyl-endo-3,3-Dimethyl-2-Norbornanol . Organic Syntheses . 1990 . 68 . 14. M. M. Midland. J. I. McLoughlin. R. T. Werley Jr..