ArticleAngewandte Chemie (International ed. in English)2016
Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed.
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- Methyl on the Bridge: 2-Methyl Propellane as Precursor for 1,3-Substituted 2-Methylated Bicyclo[1.1.1]Pentanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Second-Generation Anti-Tubercular Squaramides Targeting Complex V of the Respiratory Chain ofJournal of medicinal chemistry · 2026Article
- Efficient logRSC medicinal chemistry · 2026Article
- Which halogen to choose? Comparing the effects of chlorine and fluorine as bioisosteric substituents in drug design.Chemical science · 2026Review
- On the Nature of Improper Hydrogen Bonding in RCHAngewandte Chemie (International ed. in English) · 2026Article
- Impact of Fluorine Pattern on Lipophilicity and Acid-Base Properties of 2-(Thiofluoroalkyl)pyridines: Insights from Experiments and Statistical Modeling.Journal of medicinal chemistry · 2025Article
- Origami with small molecules: exploiting the C-F bond as a conformational tool.Beilstein journal of organic chemistry · 2025Review
- Quantifying the ability of the CFBeilstein journal of organic chemistry · 2025Article
- Synthesis and screening of a library of LewisNature communications · 2024Article
- Influence of Selective Deoxyfluorination on the Molecular Structure of Type-2The Journal of organic chemistry · 2024Review
- Conformational Analysis Explores the Role of Electrostatic Nonclassical CF···HC Hydrogen Bonding Interactions in Selectively Halogenated Cyclohexanes.The Journal of organic chemistry · 2024Article
- Preparation ofPharmaceutics · 2023Article
- Synthesis of Fluorinated Amines: A Personal Account.ACS organic & inorganic Au · 2023Review
- Obtaining PureThe Journal of organic chemistry · 2023Article
- Aryl (β,β',β″-Trifluoro)-Organic letters · 2023Article
- Drug Discovery Based on Fluorine-Containing Glycomimetics.Molecules (Basel, Switzerland) · 2023Review
- Species-specific lipophilicities of fluorinated diketones in complex equilibria systems and their potential as multifaceted reversible covalent warheads.Communications chemistry · 2023Article
- Novel N(SCFChemical science · 2023Article
- Exploring multivalent carbohydrate-protein interactions by NMR.Chemical Society reviews · 2023Review
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7 authors.
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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.
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