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Discrimination of Chiral Guests by Chiral Channels: Variable Temperature Studies by SXRD and Solid State 13C NMR of the Deoxycholic Acid Complexes of Camphorquinone and Endo-3-Bromocamphor


Citation

Mohamed I. M., Tahir and Nicholas, H. Rees and Stephen, J. Heyes and Andrew, R. Cowley and Keith, Prout (2008) Discrimination of Chiral Guests by Chiral Channels: Variable Temperature Studies by SXRD and Solid State 13C NMR of the Deoxycholic Acid Complexes of Camphorquinone and Endo-3-Bromocamphor. Chirality, 20 (7). pp. 863-870. ISSN 0899-0042

Abstract

3a,12a-Dihydroxy-5b-cholan-24-oic acid (deoxycholic acid DCA) is able to discriminate between the R- and S-enantiomers of camphorquinone and endo-(1)-3-bromocamphor and select only the S-enantiomers from a racemic mixture. DCA forms novel well ordered 1:1 adducts with (1S)-(1)-camphorquinone and (1S)-endo-(-)-3-bromocamphor, both of which have been characterized by single crystal X-ray diffraction SXRD). When DCA is cocrystallized with (RS)-camphorquinone and (RS)-endo-3-bromocamphor,1:1 adducts of the S-enantiomers are produced together with crystals of the free racemic guest. In contrast, in the absence of (1S)-(1)-camphorquinone, DCA forms a 2:1 adduct with (1R)-(2)-camphorquinone. In this 2:1 adduct the guest is disordered at ambient temperature and undergoes a phase change in the region 160–130 K similar to that observed for the ferrocene adduct, but with only partial ordering of the guest. The SXRD structure of the low temperature form and the variable temperature 13C CP/MAS NMR are reported. Cocrystallizing DCA with (1R)-endo-(1)-3-bromocamphor gives the free guest and a glassy solid.


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Official URL or Download Paper: http://dx.doi.org/10.1002/chir.20561

Additional Metadata

Item Type: Article
Divisions: Faculty of Science
DOI Number: https://doi.org/10.1002/chir.20561
Publisher: Wiley-Blackwell
Keywords: molecular complexes, chiral discrimination, chiral selection
Depositing User: Najwani Amir Sariffudin
Date Deposited: 29 Apr 2010 10:13
Last Modified: 23 Oct 2015 07:57
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.1002/chir.20561
URI: http://psasir.upm.edu.my/id/eprint/5809
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