Source:http://linkedlifedata.com/resource/pubmed/id/11112582
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
25
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| pubmed:dateCreated |
2000-12-26
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| pubmed:abstractText |
Achiral (8a) and chiral (8b) N-(2,4-dinitrobenzenesulfenyl)acridone derivatives were synthesized. Addition of the chiral solvating agent (S)- 2,2,2-trifluro-1-(anthryl)ethanol to 8a rendered the enantiotopic groups on the acridone ring diastereotopic and anisochronous, thus allowing the estimation of a lower limit for the rotational barrier about the S-N bond (18.7 kcal mol(-)(1)) by NMR spectroscopy. 8b and the previously reported chiral sulfenamide 5 (Raban, M.; Martin, V. A.; Craine, L. J. Org. Chem. 1990, 55, 4311) were resolved on a Chiracel OD HPLC column. This constitutes the first resolution of stereostable enantiomers of a compound in which the chirality is due only to the presence of the S-N chiral axis. The rotational barriers of both compounds are nearly equal (22.7-22. 8 kcal mol(-)(1) at 303.7 K) and are the largest determined to date for the rotation about the S-N bond in sulfenamides. The relatively high enantiomerization barrier for 8b is remarkable since the peri positions are unsubstituted.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Dec
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| pubmed:issn |
0022-3263
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
15
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| pubmed:volume |
65
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
8613-20
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| pubmed:dateRevised |
2003-10-31
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| pubmed:year |
2000
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| pubmed:articleTitle |
Resolution and rotational barriers of quinolinone and acridone sulfenamide derivatives: demonstration of the S-N chiral axis.
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| pubmed:affiliation |
Department of Chemistry, Ben Gurion University of the Negev, Beer-Sheva 84105, Israel.
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| pubmed:publicationType |
Journal Article
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