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Abstract

Chemistry

A New Straightforward Method for Lipophilicity (logP) Measurement using 19F NMR Spectroscopy

Published: January 30th, 2019

DOI:

10.3791/58567

1Chemistry, University of Southampton, 2Medicinal Chemistry, Oncology, IMED Biotech Unit, AstraZeneca

Abstract

Fluorination has become an effective tool to optimize physicochemical properties of bioactive compounds. One of the applications of fluorine introduction is to modulate the lipophilicity of the compound. In our group, we are interested in the study of the impact of fluorination on lipophilicity of aliphatic fluorohydrins and fluorinated carbohydrates. These are not UV-active, resulting in a challenging lipophilicity determination. Here, we present a straightforward method for the measurement of lipophilicity of fluorinated compounds by 19F NMR spectroscopy. This method requires no UV-activity. Accurate solute mass, solvent and aliquot volume are also not required to be measured. Using this method, we measured the lipophilicities of a large number of fluorinated alkanols and carbohydrates.

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Keywords Lipophilicity

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