Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography
Publication type: Journal Article
Publication date: 1999-02-13
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
11674208
Organic Chemistry
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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GOST
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Oxelbark J., Allenmark S. Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography // Journal of Organic Chemistry. 1999. Vol. 64. No. 5. pp. 1483-1486.
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Oxelbark J., Allenmark S. Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography // Journal of Organic Chemistry. 1999. Vol. 64. No. 5. pp. 1483-1486.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo981885o
UR - https://doi.org/10.1021/jo981885o
TI - Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography
T2 - Journal of Organic Chemistry
AU - Oxelbark, Joakim
AU - Allenmark, Stig
PY - 1999
DA - 1999/02/13
PB - American Chemical Society (ACS)
SP - 1483-1486
IS - 5
VL - 64
PMID - 11674208
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{1999_Oxelbark,
author = {Joakim Oxelbark and Stig Allenmark},
title = {Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography},
journal = {Journal of Organic Chemistry},
year = {1999},
volume = {64},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jo981885o},
number = {5},
pages = {1483--1486},
doi = {10.1021/jo981885o}
}
Cite this
MLA
Copy
Oxelbark, Joakim, and Stig Allenmark. “Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography.” Journal of Organic Chemistry, vol. 64, no. 5, Feb. 1999, pp. 1483-1486. https://doi.org/10.1021/jo981885o.