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Updated: Jul 27, 2025

Author Spotlight: Accelerating Discovery in Microporous Material Chemistry
Published on: October 6, 2023
The quest for organo-alkali metal monomers: unscrambling the structure-reactivity relationship
1Chemistry - School of Natural and Environmental Sciences, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. erli.lu@newcastle.ac.uk.
Abstract:
Organo-alkali metal reagents are essential tools in synthetic chemistry. Alkali metal organometallics aggregate in solution and solid-state forming clusters and polymers. The structure of these aggregates and their structure-reactivity relationship have been of great interest for many decades. This Perspective will look at the strategies that have been employed to isolate low aggregates and, in particular, monomeric complexes of the most common alkali metal alkyls (M = Li-Cs, R = methyl, trimethylsilylmethyl, bis/tris(trimethylsilylmethyl), butyls and benzyl) and the relationship between level of aggregation, structure and reactivity.
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Properties of Organometallic Compounds
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.
Relative Reactivity of Carboxylic Acid Derivatives
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
Anionic Chain-Growth Polymerization: Overview
Radical Reactivity: Electrophilic Radicals
Radical Reactivity: Nucleophilic Radicals

