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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Main Authors:	Gintautas Bagdžiūnas, Eugenijus Butkus, Sigitas Stončius
Format:	Article
Language:	English
Published:	MDPI AG 2014-07-01
Series:	Molecules
Subjects:	circular dichroism conformational analysis TD-DFT calculations transannular interactions homoconjugation
Online Access:	http://www.mdpi.com/1420-3049/19/7/9893

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spelling	doaj-1e84cbf282d94e76b62d4a12df594cc42020-11-24T23:19:33ZengMDPI AGMolecules1420-30492014-07-011979893990610.3390/molecules19079893molecules19079893Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic AcidsGintautas Bagdžiūnas0Eugenijus Butkus1Sigitas Stončius2Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, LithuaniaDepartment of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, LithuaniaDepartment of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, LithuaniaThe 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.http://www.mdpi.com/1420-3049/19/7/9893circular dichroismconformational analysisTD-DFT calculationstransannular interactionshomoconjugation
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Gintautas Bagdžiūnas Eugenijus Butkus Sigitas Stončius
spellingShingle	Gintautas Bagdžiūnas Eugenijus Butkus Sigitas Stončius Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids Molecules circular dichroism conformational analysis TD-DFT calculations transannular interactions homoconjugation
author_facet	Gintautas Bagdžiūnas Eugenijus Butkus Sigitas Stončius
author_sort	Gintautas Bagdžiūnas
title	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_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_sort	homoconjugation vs. exciton coupling in chiral α,β-unsaturated bicyclo[3.3.1]nonane dinitrile and carboxylic acids
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2014-07-01
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.
topic	circular dichroism conformational analysis TD-DFT calculations transannular interactions homoconjugation
url	http://www.mdpi.com/1420-3049/19/7/9893
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Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids

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