Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non‐UV‐Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method. (23rd November 2015)

• Record Type: Journal Article
• Authors: Linclau, Bruno; Wang, Zhong; Compain, Guillaume; Paumelle, Vincent; Fontenelle, Clement Q.; Wells, Neil; Weymouth‐Wilson, Alex
• Is Part Of: Angewandte Chemie. Volume 128:Number 2(2016)
• Page Start: 684
• Page End: 688
• Publication Date: 2015-11-23
• Subjects: Fluor -- Fluoralkohole -- Fluorierte Kohlenhydrate -- Lipophilie -- NMR‐Spektroskopie; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201509460
• Languages: English
• ISSNs: 0044-8249

Abstract

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.