Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G2G2, Canada.
Chirality. 2013 May;25(5):294-300. doi: 10.1002/chir.22147.
In the present work, we report a comprehensive vibrational circular dichroism (VCD) spectroscopic study of a chiral crown ether which features an axial chiral 3.3'-diphenyl-1,1'-binaphthyl group as chiral moiety. By comparing the experimental and calculated VCD spectra, we show that the presumably very flexible crown ether preferably adopts only one ring conformation. Conformational flexibility is observed in the 2,4-dinitrophenyl-diazophenol group, which was previously introduced for colorimetric detection of primary amines and amino alcohols (Cho et al., Chirality 2011;23:349-353). The VCD spectra of the host-guest complexes with phenyl glycinol (PG) and phenyl alaninol have been studied as well. Based on the spectra calculated, it is shown that the diastereomeric complexes in general can be differentiated using VCD spectroscopy. Furthermore, the experimental VCD spectra of the complexes of the host molecule with PG support the above finding.
在本工作中，我们报道了一种手性冠醚的全面振动圆二色性（VCD）光谱研究，该冠醚具有作为手性部分的轴向手性 3.3'-二苯基-1,1'-联萘基。通过比较实验和计算的 VCD 光谱，我们表明假定非常灵活的冠醚优选仅采用一种环构象。在 2,4-二硝基苯-diazo 苯酚基团中观察到构象灵活性，该基团先前被引入用于对伯胺和氨基醇的比色检测（Cho 等人，Chirality 2011; 23:349-353）。还研究了与苯甘氨醇（PG）和苯丙氨醇的主体-客体配合物的 VCD 光谱。基于计算的光谱，表明通常可以使用 VCD 光谱区分非对映异构体配合物。此外，主体分子与 PG 的配合物的实验 VCD 光谱支持上述发现。
