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Issue 28, 2020
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Controlling the reactions of 1-bromogalactose acetate in methanol using ionic liquids as co-solvents

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Abstract

The reactions of an acetobromogalactose in mixtures of methanol and one of seven different ionic liquids with varying constituent ions were studied. In general, small amounts of ionic liquid in the reaction mixture led to increases in the rate constant compared to methanol, whilst large amounts of ionic liquid led to decreases in the rate constant; this outcome differs significantly from previous reactions proceeding through this mechansim. Temperature dependent kinetic studies indicated that the dominant interaction driving these changes was between the ionic liquid and the transition state of the process. Through considering solvent parameters of ionic liquids, a relationship was found between the changes in the rate constant and both the hydrogen bond accepting ability and polarisability of the solvent, indicating that the interactions affecting reaction outcome are both specific and non-specific in nature; once more, these interactions were different to those observed in previous similar reactions. By changing the amount of ionic liquid in the reaction mixture, additional products not seen in the molecular solvent case were observed, the ratios of which are dependent on the anion of the ionic liquid and the proportion of ionic liquid in the reaction mixture. This demonstrates the importance of considering solvent effects on both the rate and product determining steps and the potential application of such changes is discussed.

Graphical abstract: Controlling the reactions of 1-bromogalactose acetate in methanol using ionic liquids as co-solvents

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Supplementary files

Article information


Submitted
10 Jun 2020
Accepted
28 Jun 2020
First published
02 Jul 2020

Org. Biomol. Chem., 2020,18, 5442-5452
Article type
Paper

Controlling the reactions of 1-bromogalactose acetate in methanol using ionic liquids as co-solvents

A. Gilbert, R. S. Haines and J. B. Harper, Org. Biomol. Chem., 2020, 18, 5442
DOI: 10.1039/D0OB01198C

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