Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
2009-1-30
pubmed:abstractText
Upon heating to 80 degrees C, 11-cis-retinal yields a mixture of all-trans-retinal and 13-cis-retinal. This isomerization has been studied by means of density functional theory methods, and the computational results suggest a close competition between two mechanisms of very different nature. A classical internal rotation around the C11-C12 cis double bond, via a diradical transition state, accounts for the formation of the all-trans isomer. An intricate sequence of pericyclic reactions, namely a reversible [1,7]-H sigmatropic shift and a reversible 6-pi-oxa-electrocyclic reaction, is responsible for the formation of 13-cis-retinal. Experiments using 11-cis-retinal labeled with deuterium at C19 confirmed the mechanistic proposal and also revealed an unprecedented outcome on the product composition of isotopologues.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
6
pubmed:volume
74
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1007-13
pubmed:meshHeading
pubmed:year
2009
pubmed:articleTitle
Complex thermal behavior of 11-cis-retinal, the ligand of the visual pigments.
pubmed:affiliation
Departamento de Quimica Organica, Facultade de Quimica, Universidade de Vigo, Lagoas Marcosende, E-36310, Vigo, Spain.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't