Linked Life Data

20468030

Source:http://linkedlifedata.com/resource/pubmed/id/20468030

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
25
pubmed:dateCreated
2010-6-30
pubmed:abstractText
Four novel 1,8-disubstituted naphthalene derivatives 4-7 that contain chalcogen atoms occupying the peri positions have been prepared and fully characterised by using X-ray crystallography, multinuclear NMR spectroscopy, IR spectroscopy and MS. Molecular distortion due to noncovalent substituent interactions was studied as a function of the bulk of the interacting chalcogen atoms and the size and nature of the alkyl group attached to them. X-ray data for 4-7 was compared to the series of known 1,8-bis(phenylchalcogeno)naphthalenes 1-3, which were themselves prepared from novel synthetic routes. A general increase in the E...E' distance was observed for molecules containing bulkier atoms at the peri positions. The decreased S...S distance from phenyl-1 and ethyl-4 analogues is ascribed to a weaker chalcogen lone pair-lone pair repulsion acting in the ethyl analogue due to the presence of two equatorial S(naphthyl) ring conformations. Two novel peri-substituted naphthalene sulfoxides of 1, Nap(O=SPh)(SPh) 8 and Nap(O=SPh)(2) 9, which contain different valence states of sulfur, were prepared and fully characterised by using X-ray crystallography and multinuclear NMR spectroscopy, IR spectroscopy and MS. Molecular structures were analysed by using naphthalene ring torsions, peri-atom displacement, splay angle magnitude, S...S interactions, aromatic ring orientations and quasi-linear O=S...S arrangements. The axial S(naphthyl) rings in 8 and 9 are unfavourable for S...S contacts due to stronger chalcogen lone pair-lone pair repulsion. Although quasi-linear O=S...S alignments suggest attractive interaction is conceivable, analysis of the B3LYP wavefunctions affords no evidence for direct bonding interactions between the S atoms.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jul
pubmed:issn
1521-3765
pubmed:author
pubmed:issnType
Electronic
pubmed:day
5
pubmed:volume
16
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
7503-16
pubmed:meshHeading
pubmed:year
2010
pubmed:articleTitle
Synthetic and structural studies of 1,8-chalcogen naphthalene derivatives.
pubmed:affiliation
School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST UK.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't