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A Method of Calculating the Kamlet–Abboud–Taft Solvatochromic Parameters Using COSMO-RS

Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, North Yorkshire YO10 5DD, UK
Authors to whom correspondence should be addressed.
Academic Editor: Joaquín García Álvarez
Molecules 2019, 24(12), 2209;
Received: 22 May 2019 / Revised: 7 June 2019 / Accepted: 11 June 2019 / Published: 13 June 2019
(This article belongs to the Special Issue Bio-based and Safer Solvents)
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There is demand for safer and bio-based solvents, brought on by legislation and sustainability objectives. The prediction of physical properties is highly desirable to help design new molecules. Here we present an in silico approach to obtain calculated Kamlet–Abboud–Taft solvatochromic parameters using virtual experiments. The tautomerisation equilibrium of methyl acetoacetate and dimedone was calculated in different solvents with COSMO-RS theory and converted into estimates of solvent dipolarity and hydrogen bond accepting ability, respectively. Hydrogen bond donating ability was calculated as a function of the electron deficient surface area on protic solvents. These polarity descriptors correlate with rate constants and equilibria, and so ability of calculated Kamlet–Abboud–Taft solvatochromic parameters to recreate experimental free energy relationships was tested with sixteen case studies taken from the literature. The accuracy of the calculated parameters was also satisfactory for solvent selection, as demonstrated with a 1,4-addition reaction and a multicomponent heterocycle synthesis. View Full-Text
Keywords: solvent effects; solvatochromism; polarity; kinetics; COSMO-RS solvent effects; solvatochromism; polarity; kinetics; COSMO-RS

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Sherwood, J.; Granelli, J.; McElroy, C.R.; Clark, J.H. A Method of Calculating the Kamlet–Abboud–Taft Solvatochromic Parameters Using COSMO-RS. Molecules 2019, 24, 2209.

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