OPTICAL-ACTIVITY ARISING FROM C-13 SUBSTITUTION - VIBRATIONAL CIRCULAR-DICHROISM STUDY OF (2S,3S)-CYCLOPROPANE-1-(C-13),(H-2)-2,3-(H2)-H-2

被引:34
作者
FREEDMAN, TB
CIANCIOSI, SJ
RAGUNATHAN, N
BALDWIN, JE
NAFIE, LA
机构
[1] Department of Chemistry, Syracuse University, Syracuse
关键词
D O I
10.1021/ja00022a016
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Vibrational circular dichroism (VCD) spectra of the novel chiral compound (2S,3S)-cyclopropane-1-C-13,H-2-2,3-H-2(2) (1) are reported. This quadruply labeled cyclopropane is chiral due to substitution of C-13 at carbon 1 of anti-cyclopropane-1,2,3-H-2(3) (2). In C2Cl4 solution, a conservative (+,-,+) VCD pattern is observed in both the CH and CD stretching regions. From normal-coordinate analysis, these VCD bands are found to arise from chiral perturbation which mixes the A' and A" symmetry modes of 2. Excellent quantitative agreement with the experimental VCD spectra is obtained by applying a generalized coupled-oscillator model to the motions of the two pairs of chirally oriented trans CH or CD oscillators.
引用
收藏
页码:8298 / 8305
页数:8
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