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Assessment of configurational and conformational properties of naringenin by vibrational circular dichroism
Author(s) -
Abbate Sergio,
Burgi Luigi Filippo,
Castiglioni Ettore,
Lebon France,
Longhi Giovanna,
Toscano Eleonora,
Caccamese Salvatore
Publication year - 2009
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.20616
Subject(s) - vibrational circular dichroism , chemistry , conformational isomerism , enantiomer , circular dichroism , computational chemistry , chirality (physics) , moiety , absolute configuration , crystallography , stereochemistry , molecule , organic chemistry , chiral symmetry , nambu–jona lasinio model , physics , quantum mechanics , quark
The electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra of both enantiomers of naringenin (4′,5,7‐trihydroxyflavanone) in acetonitrile solution have been measured. The enantiomers were obtained by chiral HPLC separation of the racemic sample. DFT calculations have been performed for relevant conformers and subsequent evaluations of VCD spectra are compared with VCD experiments: safe assignment of the absolute configuration is provided, based in particular on the VCD data. The relevance of the rotational conformers of the hydroxyl groups and of the mobility of phenol moiety is studied: based on this, we provide a first interpretation of the observed intense and broad couplet at 1325/1350 cm −1 . Four conformers contribute to this pattern with different sign and amplitude as shown by DFT calculations. Time dependent DFT calculations have been performed and compared with ECD experimental data, under the same assumption of conformational properties and mobilities investigated by VCD. Chirality, 2009. © 2008 Wiley‐Liss, Inc.