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Potassium tert-Butoxide: Solubility, Solution Structure, and Reactivity.

Russell F Algera¹, Nahian Khan¹, Philipp C Roosen¹

¹Pfizer Chemical Research and Development, Pfizer, Inc., Groton, Connecticut 06340, United States.

The Journal of Organic Chemistry

|March 18, 2026

Summary

This summary is machine-generated.

Potassium tert-butoxide (KOtBu) forms distinct solution structures—tetramers or monomers—depending on the solvent. This research clarifies KOtBu aggregation and reactivity, impacting its use in chemical synthesis.

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Area of Science:

Inorganic Chemistry
Physical Chemistry
Organic Synthesis

Background:

Potassium tert-butoxide (KOtBu) is a widely used strong base in organic synthesis.
Its solution behavior and aggregation state have been poorly understood, impacting reactivity.
Previous assumptions about KOtBu deaggregation in donor solvents require re-evaluation.

Purpose of the Study:

To elucidate the fundamental solution structures of KOtBu.
To correlate these structures with reactivity in dehydrohalogenation reactions.
To clarify the role of donor solvents in KOtBu aggregation and solubility.

Main Methods:

Donor solvent titration
Diffusion Nuclear Magnetic Resonance (NMR) spectroscopy
Density Functional Theory (DFT) calculations

Main Results:

KOtBu exists as unsolvated tetramers (non-Lewis basic solvents), disolvated tetramers (Lewis basic solvents), or solvated monomers (protic solvents).
Strong aprotic donor solvents do not necessarily deaggregate the KOtBu cubic tetramer.
A previously reported 1:1 KOtBu-tert-butanol complex exhibits poor solubility and reactivity.

Conclusions:

The solution structure of KOtBu is dictated by solvent properties (Lewis basicity, proticity).
Reactivity of KOtBu is enhanced by Lewis basic solvents that stabilize transition states.
Understanding KOtBu aggregation is crucial for optimizing its application in synthesis.