title: Vibrational circular dichroism and absolute configuration of chiral sulfoxides: tert-butyl methyl sulfoxide.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Southern California, Los Angeles 90089-0482, USA.
authors.forename: A
authors.initials: A
authors.lastname: Aamouche
authors.forename: F J
authors.initials: FJ
authors.lastname: Devlin
authors.forename: P J
authors.initials: PJ
authors.lastname: Stephens
authors.forename: J
authors.initials: J
authors.lastname: Drabowicz
authors.forename: B
authors.initials: B
authors.lastname: Bujnicki
authors.forename: M
authors.initials: M
authors.lastname: Mikołajczyk
mesh_terms: D002942:Circular Dichroism; D008968:Molecular Conformation; D013454:Sulfoxides / Q000737:chemistry*; D014732:Vibration
chemical_list: D013454:Sulfoxides