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Empirical Model of Solvophobic Interactions in Organic Solvents
Abstract An empirical model was developed to predict organic solvophobic effects usingN‐phenylimide molecular balances functionalized with non‐polar alkyl groups. Solution studies and X‐ray crystallography confirmed intramolecular alkyl‐alkyl interactions in theirfoldedconformers. The structural modularity of the balances allowed systematic variation of alkyl group lengths. Control balances were instrumental in isolating weak organic solvophobic effects by eliminating framework solvent‐solute effects. A19F NMR label enabled analysis across 46 deuterated and non‐deuterated solvent systems. Linear correlations were observed between organic solvophobic effects and solvent cohesive energy density (ced) as well as changes in solvent‐accessible surface areas (SASA). Using these empirical relationships, a model was constructed to predict organic solvophobic interaction energy per unit area for any organic solvent with knowncedvalues. The predicted interaction energies aligned with recent organic solvophobic measurements and literature values for the hydrophobic effect on non‐polar surfaces confirmed the model‘s accuracy and utility.
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- PAR ID:
- 10479237
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Angewandte Chemie International Edition
- Volume:
- 63
- Issue:
- 2
- ISSN:
- 1433-7851
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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