Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra.
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.
Furo
Takahiro
T
Department of Molecular Chemistry, Graduate School of Engineering, Osaka University, Suita, Japan.
Mori
Tadashi
T
Origane
Yumi
Y
Wada
Takehiko
T
Izumi
Hiroshi
H
Inoue
Yoshihisa
Y