Related Experiment Video
Updated: Jul 10, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
Determination of the absolute stereochemistry of chiral biphenanthryls in solution phase using chiroptical
Ana G Petrovic1, Sarah E Vick, Prasad L Polavarapu
1Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Abstract:
Although the exciton coupling model has been widely used in the literature to suggest the absolute configuration using electronic circular dichroism (ECD) spectra, chiral biphenanthryl systems are one group of molecules where the application of the exciton model yields ambiguous conclusions. The use of 2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol, known as VAPOL, as a chiral ligand for enantioselective catalysis necessitates the reliable determination of its absolute configuration. Based on the X-ray diffraction data of its phosphoric amide derivative, the configuration of VAPOL has been determined in the literature to be (+)-(aS). The experimental vibrational circular dichroism, ECD and optical rotatory dispersion spectra, and corresponding quantum mechanical predictions of VAPOL are used in this manuscript to independently determine its absolute configuration.
More Related Videos
Related Concept Videos
Prochirality
Properties of Enantiomers and Optical Activity
Molecules with Multiple Chiral Centers
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Stereoisomerism of Cyclic Compounds
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

