SYNTHESIS, EXPERIMENTAL AND ABINITIO THEORETICAL VIBRATIONAL CIRCULAR-DICHROISM, AND ABSOLUTE-CONFIGURATIONS OF SUBSTITUTED OXIRANES

被引:23
作者
PICKARD, ST
SMITH, HE
POLAVARAPU, PL
BLACK, TM
RAUK, A
YANG, DY
机构
[1] VANDERBILT UNIV, DEPT CHEM, NASHVILLE, TN 37235 USA
[2] UNIV CALGARY, DEPT CHEM, CALGARY T2N 1N4, ALBERTA, CANADA
关键词
D O I
10.1021/ja00043a033
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Both enantiomers of trans-2,3-dimethyloxirane-d0, trans-2,3-dimethyloxirane-2-d1, 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.
引用
收藏
页码:6850 / 6857
页数:8
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