Source:http://linkedlifedata.com/resource/pubmed/id/12569468
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
3
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| pubmed:dateCreated |
2003-2-5
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| pubmed:abstractText |
Ab initio MO calculations were carried out to examine the conformational energies of various benzylic compounds C(6)H(5)CH(2)XR (X=O, CH(2), CO, S, SO, SO(2); R=CH(3), C(2)H(5), iC(3)H(7), tC(4)H(9)) at the MP2/6-311G(d,p)//MP2/6-31G(d) level. Rotamers with R/Ph in gauche relationship are generally more stable than the R/Ph anti rotamers. In these stable geometries, the interatomic distance in the interaction of alpha- or beta-CH in the alkyl group and the ipso-carbon atom of the phenyl ring is short. The computational results are consistent with experimental data from supersonic molecular jet spectroscopy on 3-n-propyltoluene and NMR and crystallographic data on structurally related ketones, sulfoxides, and sulfones. In view of this, the alkyl/phenyl-congested conformation of these compounds has been suggested to be a general phenomenon, rather than an exception. The attractive CH/pi interaction has been suggested to be a dominant factor in determining the conformation of simple aralkyl compounds.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Feb
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| pubmed:issn |
0947-6539
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
3
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| pubmed:volume |
9
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
756-62
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| pubmed:dateRevised |
2009-8-4
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| pubmed:year |
2003
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| pubmed:articleTitle |
Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations.
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| pubmed:affiliation |
Department of Chemistry, Graduate School of Science Hiroshima University, Kagamiyama, Higashi Hiroshima 739-8526, Japan.
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| pubmed:publicationType |
Journal Article
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