title: Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method.
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.
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK). bruno.linclau@soton.ac.uk.
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK).
authors.forename: Zhong
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK).
authors.forename: Guillaume
authors.initials: G
authors.lastname: Compain
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK).
authors.forename: Vincent
authors.initials: V
authors.lastname: Paumelle
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK).
authors.forename: Clement Q
authors.initials: CQ
authors.lastname: Fontenelle
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (UK).
authors.forename: Neil
authors.initials: N
authors.lastname: Wells
authors.affiliation: Dextra Laboratories Ltd, The Science and Technology Centre, Earley Gate, Whiteknights Road, Reading RG6 6BZ (UK).
authors.forename: Alex
authors.initials: A
authors.lastname: Weymouth-Wilson
keywords: NMR spectroscopy; fluorinated carbohydrates; fluorine; fluoroalcohols; lipophilicity