Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR
A novel and efficient method for distinguishing between chiral diols and diphenols has been established through the use of 19F NMR spectroscopy. Central to this system's efficacy is a chiral amine, strategically modified with a CF3 group. This amine reacts in-situ with 2-formylphenylboronic aci...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2024-11-01
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| Series: | Magnetic Resonance Letters |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772516224000196 |
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| author | Yilin Zeng Wenjing Bao Guangxing Gu Yanchuan Zhao |
| author_facet | Yilin Zeng Wenjing Bao Guangxing Gu Yanchuan Zhao |
| author_sort | Yilin Zeng |
| collection | DOAJ |
| description | A novel and efficient method for distinguishing between chiral diols and diphenols has been established through the use of 19F NMR spectroscopy. Central to this system's efficacy is a chiral amine, strategically modified with a CF3 group. This amine reacts in-situ with 2-formylphenylboronic acid to create a chiral 19F-labeled probe. This probe demonstrates discriminatory capabilities by interacting with hydroxy-containing analytes to form boronic esters. These esters produce distinct 19F NMR signals that vary according to their stereoconfiguration, facilitating accurate chiral differentiation. The method's resolution capacity was demonstrated by successfully identifying 12 distinct chiral analytes (six pairs of enantiomers) in complex mixtures, highlighting its extensive potential in diverse chiral analysis applications. |
| format | Article |
| id | doaj-art-964687bd19aa45758edc197b26b43e25 |
| institution | Kabale University |
| issn | 2772-5162 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Magnetic Resonance Letters |
| spelling | doaj-art-964687bd19aa45758edc197b26b43e252024-11-29T06:25:33ZengKeAi Communications Co. Ltd.Magnetic Resonance Letters2772-51622024-11-0144200112Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMRYilin Zeng0Wenjing Bao1Guangxing Gu2Yanchuan Zhao3College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, China; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, ChinaKey Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, ChinaKey Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, ChinaCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, China; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, China; Instrumental Analysis Center, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China; Corresponding author. College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, China.A novel and efficient method for distinguishing between chiral diols and diphenols has been established through the use of 19F NMR spectroscopy. Central to this system's efficacy is a chiral amine, strategically modified with a CF3 group. This amine reacts in-situ with 2-formylphenylboronic acid to create a chiral 19F-labeled probe. This probe demonstrates discriminatory capabilities by interacting with hydroxy-containing analytes to form boronic esters. These esters produce distinct 19F NMR signals that vary according to their stereoconfiguration, facilitating accurate chiral differentiation. The method's resolution capacity was demonstrated by successfully identifying 12 distinct chiral analytes (six pairs of enantiomers) in complex mixtures, highlighting its extensive potential in diverse chiral analysis applications.http://www.sciencedirect.com/science/article/pii/S277251622400019619F NMRMulti-component analysisChiral discriminationEnantiocomposition |
| spellingShingle | Yilin Zeng Wenjing Bao Guangxing Gu Yanchuan Zhao Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR Magnetic Resonance Letters 19F NMR Multi-component analysis Chiral discrimination Enantiocomposition |
| title | Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR |
| title_full | Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR |
| title_fullStr | Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR |
| title_full_unstemmed | Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR |
| title_short | Enantiodifferentiation of chiral diols and diphenols via recognition-enabled chromatographic 19F NMR |
| title_sort | enantiodifferentiation of chiral diols and diphenols via recognition enabled chromatographic 19f nmr |
| topic | 19F NMR Multi-component analysis Chiral discrimination Enantiocomposition |
| url | http://www.sciencedirect.com/science/article/pii/S2772516224000196 |
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