Use of quantitative structure–property relationships to study the solvation process of 18-crown-6

• Solution enthalpies of 18-crown-6 were measured in 14 protic and aprotic solvents.
• Interaction enthalpies were analyzed on the basis of a QSPR-based approach and Solomonov’s methodology.
• π* and β were identified as the most significant intermolecular interactions underlying the solution process.
• Results were compared with previously obtained data for 1,4-dioxane.

Solution enthalpies of 18-crown-6 have been obtained for a set of 14 protic and aprotic solvents at 298.15 K. The complementary use of Solomonov’s methodology and a QSPR-based approach allowed the identification of the most significant solvent descriptors that model the interaction enthalpy contribution of the solution process (ΔintHA/S). Results were compared with data previously obtained for 1,4-dioxane. Although the interaction enthalpies of 18-crown-6 correlate well with those of 1,4-dioxane, the magnitude of the most relevant parameters, π* and β, is almost three times higher for 18-crown-6. This is rationalized in terms of the impact of the solute’s volume in the solution processes of both compounds.

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