Sherwood, James orcid.org/0000-0001-5431-2032, Granelli, Joe, McElroy, Con R orcid.org/0000-0003-2315-8153 et al. (1 more author) (2019) A Method of Calculating the Kamlet-Abboud-Taft Solvatochromic Parameters Using COSMO-RS. MOLECULES. ISSN 1420-3049
Abstract
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 by the authors |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 20 Jun 2019 15:30 |
Last Modified: | 21 Jan 2025 17:40 |
Published Version: | https://doi.org/10.3390/molecules24122209 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.3390/molecules24122209 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:147637 |