Abstract
Octanol-water partition coefficients were determined for 12 trifluoromethylated aliphatic alcohols and their unfluorinated counterparts. The latter values were derived from measurements using the benzyl alcohol-water solvent system after developing an appropriate correlation equation. Incidentally, an empirical equation was found which allows the partition coefficient of an unsubstituted alcohol to be estimated given the molecular formula and boiling point. Trifluorination strongly enhances lipophilicity only when the trifluoromethyl group is in the α-position. The enhancement is barely measurable for the β- and γ-(trifluoromethyl) alcohols, while the δ- and ϵ-(trifluoromethyl) compounds are considerably more hydrophilic than their parent compounds. Chemical shift comparisons suggest that the changes in relative lipophilicity are controlled primarily by the inductive effect of the trifluoromethyl group on the acidity-basicity of the hydroxyl group. New synthetic procedures for obtaining some of the alcohols are presented.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
