Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR
The rapid detection and differentiation of chiral compounds is important to synthetic, medicinal, and biological chemistry. Palladium complexes with chiral pincer ligands are demonstrated to have utility in determining the chirality of various amines. The binding of enantiomeric amines induces disti...
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2018
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| Online Access: | http://hdl.handle.net/1721.1/115088 |
| _version_ | 1826201700127473664 |
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| author | Zhao, Yanchuan Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Zhao, Yanchuan Swager, Timothy M |
| author_sort | Zhao, Yanchuan |
| collection | MIT |
| description | The rapid detection and differentiation of chiral compounds is important to synthetic, medicinal, and biological chemistry. Palladium complexes with chiral pincer ligands are demonstrated to have utility in determining the chirality of various amines. The binding of enantiomeric amines induces distinct ¹⁹F NMR shifts of the fluorine atoms appended on the ligand that defines a chiral environment around palladium. It is further demonstrated that this method has the ability to evaluate the enantiomeric composition and discriminate between enantiomers with chiral centers several carbons away from the binding site. The wide detection window provided by optimized chiral chemosensors allows the simultaneous identification of as many as 12 chiral amines. The extraordinary discriminating ability of this method is demonstrated by the resolution of chiral aliphatic amines that are difficult to separate using chiral chromatography. |
| first_indexed | 2024-09-23T11:55:42Z |
| format | Article |
| id | mit-1721.1/115088 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T11:55:42Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1150882024-06-27T19:14:48Z Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR Zhao, Yanchuan Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry Swager, Timothy M Zhao, Yanchuan Swager, Timothy M The rapid detection and differentiation of chiral compounds is important to synthetic, medicinal, and biological chemistry. Palladium complexes with chiral pincer ligands are demonstrated to have utility in determining the chirality of various amines. The binding of enantiomeric amines induces distinct ¹⁹F NMR shifts of the fluorine atoms appended on the ligand that defines a chiral environment around palladium. It is further demonstrated that this method has the ability to evaluate the enantiomeric composition and discriminate between enantiomers with chiral centers several carbons away from the binding site. The wide detection window provided by optimized chiral chemosensors allows the simultaneous identification of as many as 12 chiral amines. The extraordinary discriminating ability of this method is demonstrated by the resolution of chiral aliphatic amines that are difficult to separate using chiral chromatography. National Institute of General Medical Sciences (U.S.) (Grant GM095843) 2018-04-30T15:19:22Z 2018-04-30T15:19:22Z 2015-03 2015-01 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/115088 Zhao, Yanchuan, and Timothy M. Swager. “Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR.” Journal of the American Chemical Society 137, 9 (February 2015): 3221–3224 © 2015 American Chemical Society en_US http://dx.doi.org/10.1021/jacs.5b00556 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Swager via Erja Kajosalo |
| spellingShingle | Zhao, Yanchuan Swager, Timothy M Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR |
| title | Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR |
| title_full | Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR |
| title_fullStr | Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR |
| title_full_unstemmed | Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR |
| title_short | Simultaneous Chirality Sensing of Multiple Amines by ¹⁹F NMR |
| title_sort | simultaneous chirality sensing of multiple amines by ¹⁹f nmr |
| url | http://hdl.handle.net/1721.1/115088 |
| work_keys_str_mv | AT zhaoyanchuan simultaneouschiralitysensingofmultipleaminesby19fnmr AT swagertimothym simultaneouschiralitysensingofmultipleaminesby19fnmr |