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Hydroxide Chemoselectivity Changes with Water Microsolvation.

Sapir Willdorf-Cohen¹, Alexander Kaushansky², Dario R Dekel^1,3

¹The Wolfson Department of Chemical Engineering, Technion-Israel Institute of Technology, Haifa 3200003, Israel.

The Journal of Physical Chemistry Letters

|October 26, 2022

Summary

Water microsolvation alters hydroxide

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Area of Science:

Physical Chemistry
Computational Chemistry
Chemical Reactions

Background:

Solvent molecules significantly influence chemical reactions by interacting with reactants and catalysts.
Ion microsolvation, particularly in the first solvation sphere, creates strong electronic interactions, altering charge distribution and chemical properties like acidity and nucleophilicity.
Fundamental aspects of ion microsolvation effects in condensed phases remain incompletely understood.

Purpose of the Study:

To investigate how water microsolvation affects the chemoselectivity of hydroxide.
To elucidate the differential impact of microsolvation on hydroxide's basicity versus nucleophilicity.
To provide insights into the fundamental mechanisms of ion-solvent interactions in chemical reactions.

Main Methods:

Utilized reactions between hydroxide and quaternary ammonium salts as a model system.
Employed computational methods to calculate oxidation potentials and polarizabilities of water-hydroxide clusters.
Analyzed the changes in hydroxide's basicity and nucleophilicity due to microsolvation.

Main Results:

Water microsolvation demonstrably alters hydroxide's chemoselectivity.
The reactivity of hydroxide as a nucleophile is less impacted by water microsolvation compared to its reactivity as a base.
Calculated oxidation potentials and polarizabilities provide a basis for understanding these disparities in reactivity.

Conclusions:

Ion microsolvation plays a crucial role in modulating the distinct chemical properties of ions like hydroxide.
The differing effects of microsolvation on basicity and nucleophilicity explain observed changes in chemoselectivity.
This study highlights the importance of considering specific solvent-ion interactions for predicting reaction outcomes in condensed phases.