Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids

The chiroptical properties of enantiomerically pure bicyclo[3.3.1]nona-2,6-diene-2,6-dicarbonitrile and related acids were studied by circular dichroism spectroscopy and theoretical computations. A consideration of the molecular structure of the synthesized difunctional compounds revealed that chrom...

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Autores principales: Bagdžiūnas, Gintautas, Butkus, Eugenijus, Stončius, Sigitas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270784/
https://www.ncbi.nlm.nih.gov/pubmed/25006793
http://dx.doi.org/10.3390/molecules19079893
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author Bagdžiūnas, Gintautas
Butkus, Eugenijus
Stončius, Sigitas
author_facet Bagdžiūnas, Gintautas
Butkus, Eugenijus
Stončius, Sigitas
author_sort Bagdžiūnas, Gintautas
collection PubMed
description The chiroptical properties of enantiomerically pure bicyclo[3.3.1]nona-2,6-diene-2,6-dicarbonitrile and related acids were studied by circular dichroism spectroscopy and theoretical computations. A consideration of the molecular structure of the synthesized difunctional compounds revealed that chromophores are predisposed to transannular through-space interaction due to a favourable conformation of the bicyclic skeleton and a rather small interchromophoric distance. Evidence for non-exciton-type coupling between the two acrylonitrile and acrylate moieties in 3 and 4, respectively, was obtained by chiroptical spectroscopy and DFT calculations.
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spelling pubmed-62707842018-12-21 Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids Bagdžiūnas, Gintautas Butkus, Eugenijus Stončius, Sigitas Molecules Article The chiroptical properties of enantiomerically pure bicyclo[3.3.1]nona-2,6-diene-2,6-dicarbonitrile and related acids were studied by circular dichroism spectroscopy and theoretical computations. A consideration of the molecular structure of the synthesized difunctional compounds revealed that chromophores are predisposed to transannular through-space interaction due to a favourable conformation of the bicyclic skeleton and a rather small interchromophoric distance. Evidence for non-exciton-type coupling between the two acrylonitrile and acrylate moieties in 3 and 4, respectively, was obtained by chiroptical spectroscopy and DFT calculations. MDPI 2014-07-08 /pmc/articles/PMC6270784/ /pubmed/25006793 http://dx.doi.org/10.3390/molecules19079893 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bagdžiūnas, Gintautas
Butkus, Eugenijus
Stončius, Sigitas
Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
title Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
title_full Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
title_fullStr Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
title_full_unstemmed Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
title_short Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
title_sort homoconjugation vs. exciton coupling in chiral α,β-unsaturated bicyclo[3.3.1]nonane dinitrile and carboxylic acids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270784/
https://www.ncbi.nlm.nih.gov/pubmed/25006793
http://dx.doi.org/10.3390/molecules19079893
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AT stonciussigitas homoconjugationvsexcitoncouplinginchiralabunsaturatedbicyclo331nonanedinitrileandcarboxylicacids

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