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Updated: Jul 3, 2025

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Lithium, sodium and potassium enolate aggregates and monomers: syntheses and structures
Nathan Davison1, Jack M Hemingway1, Paul G Waddell1
1Chemistry-School of Natural and Environmental Sciences, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. erli.lu@newcastle.ac.uk.
Abstract:
In this Article, we report the syntheses and comparative structural studies of lithium, sodium, and potassium anthracen-9-yl enolates, as their aggregates (Li, Na: hexamer; K: tetramer) and ligand-stabilized monomers (for Li and Na). The monomers add new members to the rare collection of group-1 metal monomeric enolates. Moreover, the series covers different group-1 metal cations (Li+, Na+ and K+) and aggregate sizes, allowing comparative structural studies to elucidate how the metal identity and aggregate size influence the enolate structure.
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Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.