The robust, readily available cobalt(iii) trication [Co(NH2CHPhCHPhNH2)3]3+ is a progenitor of broadly applicable chirality and prochirality sensing agentsElectronic supplementary information (ESI) available: CCDC 1812259. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01510d

The robust, readily available cobalt(iii) trication [Co(NH2CHPhCHPhNH2)3]3+ is a progenitor of... When NMR spectra of chiral racemic organic molecules containing a Lewis basic functional group are recorded in the presence of air and water stable salts of the cobalt(iii) trication [Co((S,S)-NH2CHPhCHPhNH2)3]3+ (23+), separate signals are usually observed for the enantiomers (28 diverse examples, >12 functional groups). Several chiral molecules can be simultaneously analyzed, and enantiotopic groups in prochiral molecules differentiated (16 examples). Particularly effective are the mixed bis(halide)/tetraarylborate salts -23+ 2XBArf (X = Cl, I; BArf = B(3,5-C6H3(CF3)2)4), which are applied in CD2Cl2 or CDCl3 at 1100 mol% (avg 34 and 14 mol%). Job plots establish 1:1 binding for -23+ 2ClBArf and 1-phenylethyl acetate (4) or 1-phenylethanol (10), and ca. 1:2 binding with DMSO (CD2Cl2). Selected binding constants are determined, which range from 7.602.73 M1 for the enantiomers of 10 to 28.122.6 M1 for the enantiomers of 4. The NH moieties of the C2 faces of the trication are believed to hydrogen bond to the Lewis basic functional groups, as seen in the crystal structure of a hexakis(DMSO) solvate of -23+ 3I. These salts rank with the most broadly applicable chirality sensing agents discovered to date. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Science Royal Society of Chemistry

The robust, readily available cobalt(iii) trication [Co(NH2CHPhCHPhNH2)3]3+ is a progenitor of broadly applicable chirality and prochirality sensing agentsElectronic supplementary information (ESI) available: CCDC 1812259. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01510d

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Publisher
The Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
2041-6520
D.O.I.
10.1039/c8sc01510d
Publisher site
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Abstract

When NMR spectra of chiral racemic organic molecules containing a Lewis basic functional group are recorded in the presence of air and water stable salts of the cobalt(iii) trication [Co((S,S)-NH2CHPhCHPhNH2)3]3+ (23+), separate signals are usually observed for the enantiomers (28 diverse examples, >12 functional groups). Several chiral molecules can be simultaneously analyzed, and enantiotopic groups in prochiral molecules differentiated (16 examples). Particularly effective are the mixed bis(halide)/tetraarylborate salts -23+ 2XBArf (X = Cl, I; BArf = B(3,5-C6H3(CF3)2)4), which are applied in CD2Cl2 or CDCl3 at 1100 mol% (avg 34 and 14 mol%). Job plots establish 1:1 binding for -23+ 2ClBArf and 1-phenylethyl acetate (4) or 1-phenylethanol (10), and ca. 1:2 binding with DMSO (CD2Cl2). Selected binding constants are determined, which range from 7.602.73 M1 for the enantiomers of 10 to 28.122.6 M1 for the enantiomers of 4. The NH moieties of the C2 faces of the trication are believed to hydrogen bond to the Lewis basic functional groups, as seen in the crystal structure of a hexakis(DMSO) solvate of -23+ 3I. These salts rank with the most broadly applicable chirality sensing agents discovered to date.

Journal

Chemical ScienceRoyal Society of Chemistry

Published: May 21, 2018

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