Synthesis, experimental and ab initio theoretical vibrational circular dichroism, and absolute configurations of substituted oxiranes

Article abstract of DOI:10.1021/ja00043a033

Both enantiomers of trans-2,3-dimethyloxirane-d₀, trans-2,3-dimethyloxirane-d₂, and trans-2,3-dimethyloxirane-2,3-d₂ are synthesized. Vibrational circular dichroism (VCD) spectra for these compounds are obtained in the 1600-700-cm^-1 region. Ab initio theoretical calculations using the localized molecular orbital method (LMO-VCD) and the vibronic coupling theoretical method (VCT) are also obtained for these molecules. A comparison of the theoretical VCD predictions with the corresponding experimental observations demonstrates that the observed VCD features are satisfactorily reproduced by the theories, indicating that absolute configurations can be confidently determined using vibrational circular dichroism.