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
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...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English English |
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Wiley-Blackwell
2008
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| Online Access: | http://psasir.upm.edu.my/id/eprint/5809/ http://psasir.upm.edu.my/id/eprint/5809/1/Discrimination%20of%20Chiral%20Guests%20by%20Chiral%20Channels.pdf |
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| author | Mohamed I. M., Tahir Nicholas, H. Rees Stephen, J. Heyes Andrew, R. Cowley Keith, Prout |
| author_facet | Mohamed I. M., Tahir Nicholas, H. Rees Stephen, J. Heyes Andrew, R. Cowley Keith, Prout |
| author_sort | Mohamed I. M., Tahir |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-15T07:23:37Z |
| format | Article |
| id | upm-5809 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-15T07:23:37Z |
| publishDate | 2008 |
| publisher | Wiley-Blackwell |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-58092015-10-23T07:57:00Z http://psasir.upm.edu.my/id/eprint/5809/ 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 Mohamed I. M., Tahir Nicholas, H. Rees Stephen, J. Heyes Andrew, R. Cowley Keith, Prout 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. Wiley-Blackwell 2008 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/5809/1/Discrimination%20of%20Chiral%20Guests%20by%20Chiral%20Channels.pdf 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 http://dx.doi.org/10.1002/chir.20561 10.1002/chir.20561 English |
| spellingShingle | Mohamed I. M., Tahir Nicholas, H. Rees Stephen, J. Heyes Andrew, R. Cowley Keith, Prout 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| url | http://psasir.upm.edu.my/id/eprint/5809/ http://psasir.upm.edu.my/id/eprint/5809/ http://psasir.upm.edu.my/id/eprint/5809/ http://psasir.upm.edu.my/id/eprint/5809/1/Discrimination%20of%20Chiral%20Guests%20by%20Chiral%20Channels.pdf |