• Medientyp: E-Artikel
  • Titel: Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non‐UV‐Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method
  • Beteiligte: Linclau, Bruno; Wang, Zhong; Compain, Guillaume; Paumelle, Vincent; Fontenelle, Clement Q.; Wells, Neil; Weymouth‐Wilson, Alex
  • Erschienen: Wiley, 2016
  • Erschienen in: Angewandte Chemie, 128 (2016) 2, Seite 684-688
  • Sprache: Deutsch
  • DOI: 10.1002/ange.201509460
  • ISSN: 0044-8249; 1521-3757
  • Schlagwörter: General Medicine
  • Entstehung:
  • Anmerkungen:
  • Beschreibung: AbstractProperty 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.