Source:http://linkedlifedata.com/resource/pubmed/id/11686586
Switch to
| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
19
|
| pubmed:dateCreated |
2001-10-31
|
| pubmed:abstractText |
A [2]catenane and a [2]rotaxane have been prepared from a C2-symmetric, 2,9-diphenyl-1,10-phenanthroline-based (dpp-based) macrocycle incorporating a 1,5-dioxynaphthalene subunit by means of the transition metal templated technique. In the case of the catenane, this macrocycle is interlocked with a dpp-based macrocycle that is oriented through the location of a p-tolyl substituent in the 4-position of the phenanthroline subunit. In the case of the rotaxane, the C2-symmetric macrocycle is threaded onto an oriented, dumbbell-shaped molecule, based on the same 4-p-tolyl-1,10-phenanthroline subunit, which bears tetraarylmethane stoppers. Both species are chemically achiral molecules, yet they are composed entirely of asymmetric, mirror-image conformations. Conformational enantiomerization processes therefore take place exclusively by chiral pathways, conferring on these molecules the "rubber glove" property. However, while the molecular graph (constitutional formula) of the [2]rotaxane can be deformed into a planar and, hence, rigidly achiral representation, a feature shared by a few other compounds in the literature that have been characterized as "Euclidean rubber gloves", the molecular graph of the [2]catenane cannot be deformed in this way. It therefore has the unique property of being a chemically achiral "topological rubber glove".
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
|
| pubmed:month |
Oct
|
| pubmed:issn |
0947-6539
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:day |
1
|
| pubmed:volume |
7
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
4085-96
|
| pubmed:dateRevised |
2009-8-4
|
| pubmed:year |
2001
|
| pubmed:articleTitle |
A [2]catenane and a [2]rotaxane as prototypes of topological and Euclidean molecular "rubber gloves".
|
| pubmed:affiliation |
Laboratoire de Chimie Organo-Minérale, UMR 7513 du CNRS, Université Louis Pasteur, Institut Le Bel, Strasbourg, France. chambron@chimie.u-strasbg.fr
|
| pubmed:publicationType |
Journal Article
|