Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography
Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the...
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| Vydáno v: | Journal of organic chemistry Ročník 64; číslo 5; s. 1483 |
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| Hlavní autoři: | , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
| Vydáno: |
United States
05.03.1999
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| ISSN: | 1520-6904, 1520-6904 |
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| Abstract | Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the barriers to stereoinversion at sulfur were found to be around 80 kJ/mol and relatively insensitive to effects from substituents in the N-aryl group. Throughout the series the (+)-forms (436 nm) were found to be of (S)-configuration. |
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| AbstractList | Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the barriers to stereoinversion at sulfur were found to be around 80 kJ/mol and relatively insensitive to effects from substituents in the N-aryl group. Throughout the series the (+)-forms (436 nm) were found to be of (S)-configuration. Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the barriers to stereoinversion at sulfur were found to be around 80 kJ/mol and relatively insensitive to effects from substituents in the N-aryl group. Throughout the series the (+)-forms (436 nm) were found to be of (S)-configuration.Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the barriers to stereoinversion at sulfur were found to be around 80 kJ/mol and relatively insensitive to effects from substituents in the N-aryl group. Throughout the series the (+)-forms (436 nm) were found to be of (S)-configuration. |
| Author | Allenmark, Stig Oxelbark, Joakim |
| Author_xml | – sequence: 1 givenname: Joakim surname: Oxelbark fullname: Oxelbark, Joakim organization: Department of Chemistry, Göteborg University, SE-41296 Göteborg, Sweden – sequence: 2 givenname: Stig surname: Allenmark fullname: Allenmark, Stig |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/11674208$$D View this record in MEDLINE/PubMed |
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| Title | Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography |
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