
doi: 10.1002/chir.22770
pmid: 28981965
AbstractThe absolute configurations of the separated enantiomers of fluralaner, a racemic animal health product used to prevent fleas and ticks, have been assigned using vibrational circular dichroism (VCD). The crystallographic structure of the active enantiomer (+)‐fluralaner has previously been shown to have the (S) configuration using small molecule crystallography. We sought a faster analytical method to determine the absolute configuration of the separated enantiomers. When comparing the measured IR (infrared) and VCD spectra, it is apparent that the amide carbonyl groups appear in the IR but are nearly absent in the VCD. Computational work to calculate the VCD and IR using in vacuo models, implicit solvation, and explicitly solvated complexes has implicated conformational averaging of the carbonyl VCD intensities.
Circular Dichroism, Molecular Conformation, Stereoisomerism, Isoxazoles, Amides, Vibration
Circular Dichroism, Molecular Conformation, Stereoisomerism, Isoxazoles, Amides, Vibration
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