title: Refined model of optical activity of cis-dihydrodiol metabolites: role of 1,3-diene conformation in the electronic circular dichroism spectra.
abstract: The effect of the secondary structural feature, that is, nonplanarity of carbon-carbon double bonds, on the rotatory strength of the long-wavelength π-π* electronic transition has been investigated for the series of monocyclic cis-dihydrodiol arene metabolites and model compounds. The contribution from nonplanar C=C bonds to the overall rotatory strength of the π-π* electronic transition is more significant than the contribution from twisted 1,3-diene chromophore. The effect of the substitution pattern in the cyclohexadiene skeleton may be decisive for the sign of the long-wavelength π-π* Cotton effect.
authors.affiliation: Department of Chemistry, A. Mickiewicz University, Poznan 60-780, Poland. Marcin.Kwit@amu.edu.pl
authors.forename: Marcin
authors.initials: M
authors.lastname: Kwit
authors.forename: Jacek
authors.initials: J
authors.lastname: Gawronski
mesh_terms: D002942:Circular Dichroism / Q000379:methods*; D003198:Computer Simulation; D004735:Energy Transfer; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism*; D009904:Optical Rotation
chemical_list: D009281:Naphthalenes; C507866:trans-1,2-dihydro-1,2-naphthalenediol