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• W2946457584 abstract "The effects of the CF2H moiety on H-bond (HB) acidity and lipophilicity of various compounds, when attached directly to an aromatic ring or to other functions like alkyls, ethers/thioethers, or electron-withdrawing groups, are discussed. It was found that the CF2H group acts as a HB donor with a strong dependence on the attached functional group (A = 0.035–0.165). Regarding lipophilicity, the CF2H group may act as a more lipophilic bioisostere of OH but as a similar or less lipophilic bioisostere of SH and CH3, respectively, when attached to Ar or alkyl. In addition, the lipophilicity of ethers, sulfoxides, and sulfones is dramatically increased upon CH3/CF2H exchange at the α position. Interestingly, this exchange significantly affects not only the polarity and the volume of the solutes but also their HB-accepting ability, the main factors influencing log Poct. Accordingly, this study may be helpful in the rational design of drugs containing this moiety." @default.
• W2946457584 created "2019-05-29" @default.
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• W2946457584 date "2019-05-15" @default.
• W2946457584 modified "2023-10-11" @default.
• W2946457584 title "CF₂H, a Functional Group-Dependent Hydrogen-Bond Donor: Is It a More or Less Lipophilic Bioisostere of OH, SH, and CH₃?" @default.
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• W2946457584 doi "https://doi.org/10.1021/acs.jmedchem.9b00604" @default.
• W2946457584 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/31091098" @default.
• W2946457584 hasPublicationYear "2019" @default.
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