Source:http://linkedlifedata.com/resource/pubmed/id/12515456
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
1
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| pubmed:dateCreated |
2003-1-7
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| pubmed:abstractText |
The synthesis and conformational properties of 2,6-bis-[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbam oylpyridines, 2, have been described. Bisoxazoline 2a was prepared in five steps from 2-nitrobenzoyl chloride in an overall yield of 71%. In contrast to related structures such as 1, bisoxazoline 2a exhibits a highly biased P-type helical conformation in solution and in the solid state. In the crystal lattice, 2a further assembles into a left-handed helical superstructure aligned along the crystallographic c axis. The barrier to helical interconversion, as measured by line-shape analysis of the temperature-dependent (1)H NMR spectra of thiobenzyl derivative 2b, was determined to be quite low ((Delta)G(++) = 12.3 kcal/mol), indicating the presence of a highly dynamic helical chirality.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Jan
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| pubmed:issn |
0022-3263
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
10
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| pubmed:volume |
68
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
22-6
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| pubmed:dateRevised |
2003-11-4
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| pubmed:year |
2003
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| pubmed:articleTitle |
Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline.
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| pubmed:affiliation |
Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA.
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| pubmed:publicationType |
Journal Article
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