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Vibrational Circular Dichroism Discrimination of Diastereomeric Cedranol Acetates
Author(s) -
GordilloRomán Bárbara,
CamachoRuiz Jorge,
Bucio María A.,
JosephNathan Pedro
Publication year - 2013
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.22238
Subject(s) - diastereomer , chemistry , vibrational circular dichroism , circular dichroism , spectral line , infrared spectroscopy , density functional theory , absolute configuration , spectroscopy , analytical chemistry (journal) , stereochemistry , crystallography , computational chemistry , organic chemistry , physics , quantum mechanics , astronomy
The reliability of vibrational circular dichroism (VCD) spectroscopy to discriminate four diastereomeric cedranol acetates 1 , 2 , 3 , 4 by means of their absolute configuration is examined. The usage of Compare VOA software to quantify comparisons of the measured infrared (IR) and VCD spectra with the corresponding simulated spectra at the B3LYP/DGDZVP and B3PW91/DGDZVP levels of theory for each diastereomer enabled the B3PW91 functional to be qualified as superior to the B3LYP functional for vibrational calculations of 1 , 2 , 3 , 4 . Analogously, a set of quantitative VCD spectra cross‐comparisons of 1 , 2 , 3 , 4 unambiguously distinguished the diastereomers using B3PW91 and failed using B3LYP. Remarkably, quantitative IR spectra cross‐comparisons of 1 , 2 , 3 , 4 using B3PW91 or B3LYP functionals demonstrated that the achiral spectroscopic IR technique is not able to distinguish cedranol acetate diastereomers. VCD comparisons using anisotropy g ‐factor values of bands in the 1550–950 cm ‐1 region of the spectra were of aid to facilitate visual spectra matching for each diastereomer. Chirality 25:939‐951, 2013 . © 2013 Wiley Periodicals, Inc.