Linked Life Data

20237676

Source:http://linkedlifedata.com/resource/pubmed/id/20237676

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
7
pubmed:dateCreated
2010-3-18
pubmed:abstractText
The reactivity of aromatic dicarboxylic acids, in combination with an axially-chiral, suitable dibenzylic alcohol, derived from BINOL, has been exploited in one-pot esterification reactions for the direct formation of several rigid, homochiral macrocycles. Cyclic adducts possessing, respectively, average molecular D(2) and D(3) symmetries, have been characterized in pure forms, with isolated yields and selectivities which are substantially different from those rising from purely statistical arguments. NMR and CD spectroscopies detect the structural and shape variability in the scaffolds, reflected both in terms of large changes in chemical shifts of selected proton resonances, and in terms of the variation of the CD signature related to the dihedral angle defined by the binaphthyl units embedded in the rigid cyclic skeleton. The crystal structure of two homochiral D(2) macrocycles show the formation of ordered nanostructures in the solid state, with the naphthyl rings of the binaphthyl units packing intermolecularly in an eclipsed-like conformation to yield nonhelical tubular arrangements. The larger D(3) cyclic adducts are able to afford stable complexes with C(60) in toluene solution, with comparable binding strengths, yet whose stoichiometries are dependent on small variations in the spacing units and therefore in the shapes of the internal cavities of the cyclic structures.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Apr
pubmed:issn
1477-0539
pubmed:author
pubmed:issnType
Electronic
pubmed:day
7
pubmed:volume
8
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1640-9
pubmed:year
2010
pubmed:articleTitle
Structurally-variable, rigid and optically-active D2 and D3 macrocycles possessing recognition properties towards C60.
pubmed:affiliation
Department of Organic Chemistry, University of Pavia, Viale Taramelli, 10-27100-Pavia, Italy.
pubmed:publicationType
Journal Article