通过理论与实验振动圆二色光谱的比较确定供体-受体[2.2]对环芳烷的绝对构型
Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra.
作者信息
Furo Takahiro, Mori Tadashi, Origane Yumi, Wada Takehiko, Izumi Hiroshi, Inoue Yoshihisa
机构信息
Department of Molecular Chemistry, Graduate School of Engineering, Osaka University, Suita, Japan.
出版信息
Chirality. 2006 Feb;18(3):205-11. doi: 10.1002/chir.20233.
Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7-bis(methoxycarbonyl)-12,15-dimethoxy-[2.2]paracyclophanes (1 and 2), and density functional theory (DFT) calculations were performed at the B3LYP/6-31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)-enantiomers as (4S(p);12S(p))-1 and (4S(p);12R(p))-2, respectively.
通过振动圆二色性（VCD）光谱对非对映体4,7-双（甲氧基羰基）-12,15-二甲氧基-[2.2]对环芳烷（1和2）的绝对构型进行了归属，并在B3LYP/6-31G(d)水平上对1和2的所有可能构象进行了密度泛函理论（DFT）计算，以给出理论VCD光谱。对所获得的实验和理论VCD光谱进行比较，明确确定了右旋（+）-对映体的绝对构型分别为（4S(p);12S(p)）-1和（4S(p);12R(p)）-2。
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