Solubility and Reactions of Alkali Metal Acetylides in Liquid Ammonia

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Acetylides contain an anionic building block which is comprised of two carbon atoms ((C2)2-), the protonation of which generates the gaseous hydrocarbon acetylene (C2H2). Prior to the industrial utilization of mineral oil, calcium acetylide synthesized from coal had been the main access to the organic chemistry of hydrocarbons; with the end of the petroleum age the chemistry of acetylides will regain a high profile. The authors of the proposal could demonstrate in preliminary studies that alkali metal acetylides dissolve in liquid ammonia to a small extent. Previously, (C2)2- anions could only be studied in the solid state. In the proposed project it is planned to investigate the exact conditions of this solubility as well as reactions with different reactants. In the course of this, a decisive issue is the protonation equilibrium in liquid ammonia, which leads to the presence of dissolved acetylene. The experiments conducted up to now indicate that the proposed project may open a door to a solution-based acetylide chemistry for the first time.