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Solubility predictions for solid nitriles and tertiary amides based on the mobile order theory
1Institut d'Analyse Pharmaceutique, Ecole de Pharmacie, Université de Lausanne, Switzerland.
Pharmaceutical Research
|February 1, 1994
Summary
Solubility predictions for nitriles and amides in organic solvents were made using mobile order theory. Hydrogen bond stability constants were determined, showing alcohols decrease solubility due to hydrophobic effects.
Area of Science:
- Physical Chemistry
- Thermodynamics
- Solution Chemistry
Background:
- Understanding solute solubility in various solvents is crucial for chemical processes.
- Predicting solubility aids in solvent selection and process optimization.
- Mobile order theory provides a framework for predicting solubilities based on molecular interactions.
Purpose of the Study:
- To predict the solubilities of specific nitriles and amides in organic solvents.
- To apply the mobile order theory to systems involving hydrogen bonding.
- To quantify the impact of hydrogen bonding and hydrophobic effects on solubility.
Main Methods:
- Utilized the solubility equation derived from the mobile order theory.
- Incorporated stability constants to model hydrogen bond formation.
- Calculated solubilities for hexadecanenitrile, octadecanenitrile, N,N-diphenyl capramide, and N,N-diphenyl lauramide.
Main Results:
- Determined characteristic values for nitrile-alcohol (175 cm3 mol-1) and tertiary amide-alcohol (600 cm3 mol-1) hydrogen bonds.
- Predicted solubilities in common organic nonelectrolyte solvents.
- Observed that while specific interactions increase solubility, alcohols decrease it due to hydrophobic effects.
Conclusions:
- Mobile order theory successfully predicts solubilities of nitriles and amides in organic solvents.
- Hydrogen bonding and hydrophobic effects significantly influence solubility in alcohol solvents.
- The determined stability constants provide quantitative insights into solute-solvent interactions.