title: Homoconjugation vs. exciton coupling in chiral α,β-unsaturated bicyclo[3.3.1]nonane dinitrile and carboxylic acids.
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.
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania. gintautas.bagdziunas@ktu.lt.
authors.forename: Gintautas
authors.initials: G
authors.lastname: Bagdžiūnas
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania. eugenijus.butkus@chf.vu.lt.
authors.forename: Eugenijus
authors.initials: E
authors.lastname: Butkus
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania. sigitas.stoncius@chf.vu.lt.
authors.forename: Sigitas
authors.initials: S
authors.lastname: Stončius
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000473:Alkanes; D002264:Carboxylic Acids; C017573:nonane