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A New Straightforward Method for Lipophilicity logP Measurement using 19F NMR Spectroscopy
Published on: January 30, 2019
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A New Straightforward Method for Lipophilicity (logP) Measurement using 19F NMR Spectroscopy
Zhong Wang1, Benjamin F Jeffries1, Hannah R Felstead1
1Chemistry, University of Southampton.
Journal of Visualized Experiments : Jove
|February 19, 2019
Summary
We developed a novel 19F NMR method to measure lipophilicity in fluorinated compounds, overcoming challenges with UV-inactive molecules. This technique simplifies lipophilicity determination for fluorinated alkanols and carbohydrates.
Area of Science:
- Medicinal Chemistry
- Organic Chemistry
- Analytical Chemistry
Background:
- Fluorination is key to optimizing bioactive compound properties, particularly lipophilicity.
- Traditional lipophilicity assays struggle with UV-inactive compounds like fluorinated alkanols and carbohydrates.
Purpose of the Study:
- To present a straightforward method for measuring lipophilicity in fluorinated compounds.
- To address the limitations of UV-based assays for non-UV-active molecules.
Main Methods:
- Utilized 19F NMR spectroscopy for lipophilicity determination.
- Developed a method that does not require UV activity, accurate solute mass, solvent, or aliquot volume measurements.
Main Results:
- Successfully measured the lipophilicity of numerous fluorinated alkanols and carbohydrates.
- Demonstrated the method's applicability to a wide range of fluorinated compounds.
Conclusions:
- 19F NMR spectroscopy offers a robust and simplified approach to lipophilicity assessment for fluorinated compounds.
- This method enhances the study of fluorinated bioactive molecules by enabling accurate lipophilicity profiling.
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