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.
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. 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. Monosodium acetylide can be used as a strong nucleophile in organic synthesis. However, it has largely been displaced in this application by monolithium acetylide, which can be prepared more easily. 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.
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