Particular interest has grown around the study of the intramolecular hydrogen bonding strength between a hydrogen and an adjacent C-F bond, referred to as a carbon-fluorine hydrogen bond (CFHB) - this may elucidate the potential for more effective drug delivery and agrochemical advancements. In this study, 4-tert-butylcyclohexanone was fluorinated using Selectfluor and the product separated using column chromatography. The eluate was reduced using L-Selectride at -78°C under nitrogen to elicit isomers of the alcohol. Both following fluorination and reduction, 19F and 1H NMR were taken, each congruent with literature data. What remains to be done is the establishment of a more effective separation method following the Selectfluor step so that individual compounds can be measured. Then, assessment of the strength of the intramolecular hydrogen bond can be done using a series of dilutions with DMSO and quantifying the shift in hydrogen bonding by 1H NMR.

4-tert-Butylcylcohexanone as a candidate to study and confirm existence of carbon-fluorine hydrogen bonding

2019 Spring National Meeting

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