{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Yang S"],"funding":["Chinese Academy of Sciences","Natural Science Foundation of Fujian Province"],"pagination":["318"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6536038"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["7"],"pubmed_abstract":["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 <sup>19</sup>F 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<sub>α-F <sup><i>R,S</i></sup> </sub> of (R)-FPA-(R)-amide/(S)-FPA-(R)-amide, if the experimental Δδ<sub>α-F <sup><i>R,S</i></sup> </sub> has the same symbol (positive or negative) as one of the theoretical Δδ<sub>α-F <sup><i>R,S</i></sup> </sub> , 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."],"journal":["Frontiers in chemistry"],"pubmed_title":["Assigning the Absolute Configurations of Chiral Primary Amines Based on Experimental and DFT-Calculated <sup>19</sup>F Nuclear Magnetic Resonance."],"pmcid":["PMC6536038"],"funding_grant_id":["No. 191 2018J01029","No. XDB20000000"],"pubmed_authors":["Song L","Sa R","Yang S","Bian G"],"additional_accession":[]},"is_claimable":false,"name":"Assigning the Absolute Configurations of Chiral Primary Amines Based on Experimental and DFT-Calculated <sup>19</sup>F Nuclear Magnetic Resonance.","description":"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 <sup>19</sup>F 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<sub>α-F <sup><i>R,S</i></sup> </sub> of (R)-FPA-(R)-amide/(S)-FPA-(R)-amide, if the experimental Δδ<sub>α-F <sup><i>R,S</i></sup> </sub> has the same symbol (positive or negative) as one of the theoretical Δδ<sub>α-F <sup><i>R,S</i></sup> </sub> , 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.","dates":{"release":"2019-01-01T00:00:00Z","publication":"2019","modification":"2025-04-04T10:15:02.911Z","creation":"2019-07-24T07:04:59Z"},"accession":"S-EPMC6536038","cross_references":{"pubmed":["31165055"],"doi":["10.3389/fchem.2019.00318"]}}