Vibrational circular dichroism and absolute configuration of chiral sulfoxides: tert-butyl methyl sulfoxide.
Mid-infrared vibrational unpolarised absorption and vibrational circular dichroism (VCD) spectra of CCl4 solutions of tert-butyl methyl sulfoxide (1) are reported. The spectra are compared to ab initio density functional theory (DFT) calculations carried out using two functionals, B3PW91 and B3LYP, and two basis sets, 6-31G* and TZ2P. The VCD spectra are calculated using Gauge-invariant atomic orbitals (GIAOs). The analysis of the VCD spectrum confirms the R(-)/S(+) absolute configuration of 1. The advantages and disadvantages of VCD spectroscopy in determining the absolute configurations of chiral sulfoxides are discussed.
Aamouche
A
A
Department of Chemistry, University of Southern California, Los Angeles 90089-0482, USA.
Devlin
F J
FJ
Stephens
P J
PJ
Drabowicz
J
J
Bujnicki
B
B
Mikołajczyk
M
M
D002942:Circular Dichroism; D008968:Molecular Conformation; D013454:Sulfoxides / Q000737:chemistry*; D014732:Vibration
D013454:Sulfoxides