biostudies-literatureYang SChinese Academy of SciencesNatural Science Foundation of Fujian Province318https://www.ebi.ac.uk/biostudies/studies/S-EPMC6536038biostudies-literatureUnknown7In this work, a novel method for assigning the absolute configuration of a chiral primary amine has been developed based on the experimental and DFT-calculated ¹⁹F NMR chemical shift differences of its derived two fluorinated amides by reacting with two enantiomers of a chiral derivatizing agent FPP (α-fluorinated phenylacetic phenylselenoester) separately. Comparing the experimental chemical shift difference Δ δ α - F R , S of (R)-FPA-amide/(S)-FPA-amide with the calculated Δδ_{α-F ^<i>R,S</i>} of (R)-FPA-(R)-amide/(S)-FPA-(R)-amide, if the experimental Δδ_{α-F ^<i>R,S</i>} has the same symbol (positive or negative) as one of the theoretical Δδ_{α-F ^<i>R,S</i>} , the assigned configuration of the amine is considered to be consistent with the theoretical one. Our method could be applied to a broad substrate scope avoiding wrong conclusion due to empirical judgment.Frontiers in chemistryAssigning the Absolute Configurations of Chiral Primary Amines Based on Experimental and DFT-Calculated ¹⁹F Nuclear Magnetic Resonance.PMC6536038No. 191 2018J01029No. XDB20000000Song LSa RYang SBian GfalseAssigning the Absolute Configurations of Chiral Primary Amines Based on Experimental and DFT-Calculated ¹⁹F Nuclear Magnetic Resonance.In this work, a novel method for assigning the absolute configuration of a chiral primary amine has been developed based on the experimental and DFT-calculated ¹⁹F NMR chemical shift differences of its derived two fluorinated amides by reacting with two enantiomers of a chiral derivatizing agent FPP (α-fluorinated phenylacetic phenylselenoester) separately. Comparing the experimental chemical shift difference Δ δ α - F R , S of (R)-FPA-amide/(S)-FPA-amide with the calculated Δδ_{α-F ^<i>R,S</i>} of (R)-FPA-(R)-amide/(S)-FPA-(R)-amide, if the experimental Δδ_{α-F ^<i>R,S</i>} has the same symbol (positive or negative) as one of the theoretical Δδ_{α-F ^<i>R,S</i>} , the assigned configuration of the amine is considered to be consistent with the theoretical one. Our method could be applied to a broad substrate scope avoiding wrong conclusion due to empirical judgment.2019-01-01T00:00:00Z20192025-04-04T10:15:02.911Z2019-07-24T07:04:59ZS-EPMC65360383116505510.3389/fchem.2019.00318