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Updated: Jul 3, 2025

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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.
This study details the synthesis and structural analysis of lithium, sodium, and potassium anthracen-9-yl enolates. Findings reveal how metal type and aggregation impact enolate structures, expanding knowledge of rare monomeric enolates.
Area of Science:
- Organometallic Chemistry
- Solid-State Chemistry
- Coordination Chemistry
Background:
- Enolates are key intermediates in organic synthesis.
- Group 1 metal enolates are less understood structurally compared to other metals.
- Monomeric group 1 metal enolates are particularly rare.
Purpose of the Study:
- To synthesize and structurally characterize lithium, sodium, and potassium anthracen-9-yl enolates.
- To investigate the influence of metal cation identity (Li+, Na+, K+) on enolate structure.
- To compare the structures of different aggregate sizes (hexamers, tetramers, monomers).
Main Methods:
- Synthesis of lithium, sodium, and potassium anthracen-9-yl enolates.
- X-ray crystallography for detailed structural analysis of aggregates and monomers.
- Comparative structural analysis based on metal identity and aggregation state.
Main Results:
- Successful synthesis of hexameric and tetrameric aggregates for Li, Na, and K anthracen-9-yl enolates.
- Isolation and characterization of rare monomeric lithium and sodium anthracen-9-yl enolates.
- Demonstration of distinct structural variations influenced by metal cation size and coordination environment.
Conclusions:
- The structural diversity of group 1 metal anthracen-9-yl enolates is significantly affected by both metal identity and aggregate size.
- The study expands the known examples of rare monomeric group 1 metal enolates.
- Provides a foundation for understanding structure-property relationships in alkali metal enolates.
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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.