Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non‐UV‐Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method |
| |
Authors: | Prof. Dr. Bruno Linclau Zhong Wang Dr. Guillaume Compain Vincent Paumelle Dr. Clement Q. Fontenelle Dr. Neil Wells Dr. Alex Weymouth‐Wilson |
| |
Affiliation: | 1. Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK);2. Dextra Laboratories Ltd, The Science and Technology Centre, Earley Gate, Whiteknights Road, Reading RG6 6BZ (UK) |
| |
Abstract: | Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (log P) modulation. However, the determination of log P is cumbersome for non‐UV‐active compounds. A new variation of the shake‐flask log P determination method is presented, enabling the measurement of log P for fluorinated compounds with or without UV activity regardless of whether they are hydrophilic or lipophilic. No calibration curves or measurements of compound masses/aliquot volumes are required. With this method, the influence of fluorination on the lipophilicity of fluorinated aliphatic alcohols was determined, and the log P values of fluorinated carbohydrates were measured. Interesting trends and changes, for example, for the dependence on relative stereochemistry, are reported. |
| |
Keywords: | fluorinated carbohydrates fluorine fluoroalcohols lipophilicity NMR spectroscopy |
|
|