A QSPR study on the solvent-induced frequency shifts of acetone and dimethyl sulfoxide in organic solvents

•Quantitative structure–property relationships•Deformable, contact, non-deformable and non-contact electron attributes•Electron flow, electrostatic, polarization and hydrophilic interactions•The solvent-induced frequency shifts in the infrared spectrum of acetone and dimethyl sulfoxide

In this study, solvent-induced frequency shifts (SIFS) in the infrared spectrum of acetone and dimethyl sulfoxide in organic solvents were investigated by using four types of quantum-chemical reactivity descriptors. The results showed that the SIFS of acetone is mainly affected by the electron-acceptance chemical potential and the maximum nucleophilic condensed local softness of organic solvents, which represent the electron flow and the polarization between acetone and solvent molecules. On the other hand, the SIFS of dimethyl sulfoxide changes with the maximum positive charge of hydrogen atom and the inverse of apolar surface area of solvent molecules, showing that the electrostatic and hydrophilic interactions are main mechanisms between dimethyl sulfoxide and solvent molecules. The introduction of the four-element theory model-based quantitative structure–property relationship approach improved the assessing quality and provided a basis for interpreting the solute–solvent interactions.

Graphical abstractSolvent-induced frequency shifts (SIFS) in the infrared spectrum of acetone and dimethyl sulfoxide in organic solvents were investigated by using the four-element theory model-based quantitative structure–property relationship approach. The results showed that the SIFS of acetone is mainly affected by the electron-acceptance chemical potential and the maximum nucleophilic condensed local softness of organic solvents, which represent the electron flow and the polarization between acetone and solvent molecules. On the other hand, the SIFS of dimethyl sulfoxide changes with the maximum positive charge of hydrogen atom and the inverse of apolar surface area of solvent molecules, showing that the electrostatic and hydrophilic interactions are main mechanisms between dimethyl sulfoxide and solvent molecules.Figure optionsDownload full-size imageDownload as PowerPoint slide