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Monosodium acetylide
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<p>Monosodium acetylide, also known as sodium hydrogen acetylide, is an <a href="/facts/Organosodium_compound/4raxp9E1">organosodium compound</a> with the formula NaC≡CH. It is a <a href="/facts/Sodium/eYuSPu2V">sodium</a> <a href="/facts/Salt_(chemistry)/lsSKwGpn">salt</a> of <a href="/facts/Acetylene/yaDh6cmJ">acetylene</a>, consisting of sodium <a href="/facts/Cations/wrbwhF3z">cations</a> (Na+) and hydrogen acetylide <a href="/facts/Anions/wrbwhF3z">anions</a> (−C≡CH).[<i>contradictory</i>] It is a derived from acetylene by <a href="/facts/Deprotonation/SmUSh369">deprotonation</a> using a sodium <a href="/facts/Base_(chemistry)/M9wA7qeM">base</a>, typically <a href="/facts/Sodium_amide/VbNjnp43">sodium amide</a>. </p> HC≡CH + NaNH2 → NaC≡CH + <a href="/facts/Ammonia/MtLtJFtz">NH3</a> <p>This compound, a white solid, has been characterized by <a href="/facts/Neutron_diffraction/fYXAunDW">neutron diffraction</a>, which revealed an Na-C bond and a C≡C bond of 127 <a href="/facts/Picometre/Cb54mVBX">pm</a>, which is longer than the C≡C bond length in acetylene itself (120.4 pm). </p><p>Monosodium acetylide can be used as a strong <a href="/facts/Nucleophile/xYccoaJQ">nucleophile</a> in <a href="/facts/Organic_synthesis/aprl6Iq7">organic synthesis</a>. However, it has largely been displaced in this application by monolithium acetylide, which can be prepared more easily. </p><p>Monosodium acetylide <a href="/facts/Hydrolizes/JTvwIHPs">hydrolizes</a> in contact with water, producing <a href="/facts/Sodium_hydroxide/xjtdYtq7">sodium hydroxide</a> and acetylene. </p> NaC≡CH + H2O → HC≡CH + NaOH <p>Monosodium acetylide is used in the <a href="/facts/Nef_synthesis/XnHefodE">Nef synthesis</a>. </p>