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Refined model of optical activity of cis ‐dihydrodiol metabolites: Role of 1,3‐diene conformation in the electronic circular dichroism spectra
Author(s) -
Kwit Marcin,
Gawronski Jacek
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20974
Subject(s) - chemistry , chromophore , circular dichroism , chirality (physics) , cotton effect , diene , sign (mathematics) , molecular electronic transition , wavelength , asymmetric carbon , crystallography , spectral line , stereochemistry , photochemistry , optically active , molecule , organic chemistry , chiral symmetry , mathematical analysis , mathematics , physics , natural rubber , optoelectronics , quantum mechanics , astronomy , nambu–jona lasinio model , quark
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 CC 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. Chirality, 2011. © 2011 Wiley‐Liss, Inc.