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Molecules 2014, 19(7), 9893-9906; doi:10.3390/molecules19079893

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

1
Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania
2
Present address: Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilėnų pl. 19, 50254 Kaunas, Lithuania
*
Author to whom correspondence should be addressed.
Received: 4 May 2014 / Revised: 3 June 2014 / Accepted: 5 June 2014 / Published: 8 July 2014
(This article belongs to the Special Issue Dynamic Stereochemistry)
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Abstract

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. View Full-Text
Keywords: circular dichroism; conformational analysis; TD-DFT calculations; transannular interactions; homoconjugation circular dichroism; conformational analysis; TD-DFT calculations; transannular interactions; homoconjugation
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Bagdžiūnas, G.; Butkus, E.; Stončius, S. Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids. Molecules 2014, 19, 9893-9906.

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