Absolute configuration of an axially chiral sulfonate determined from its optical rotatory dispersion, electronic circular dichroism, and vibrational circular dichroism spectra

Cody L Covington; Vijay Raghavan; Jonathan P Smuts; Daniel W Armstrong; Prasad L Polavarapu

doi:10.1002/chir.22739

Absolute configuration of an axially chiral sulfonate determined from its optical rotatory dispersion, electronic circular dichroism, and vibrational circular dichroism spectra

Chirality. 2017 Nov;29(11):670-676. doi: 10.1002/chir.22739. Epub 2017 Aug 18.

Authors

Cody L Covington¹, Vijay Raghavan¹, Jonathan P Smuts², Daniel W Armstrong², Prasad L Polavarapu¹

Affiliations

¹ Department of Chemistry, Vanderbilt University, Nashville, Tennessee, USA.
² Department of Chemistry, University of Texas at Arlington, Arlington, Texas, USA.

PMID: 28833487
DOI: 10.1002/chir.22739

Abstract

The absolute configuration (AC) of an axially chiral sulfonate (aCSO), 3,5-dimethyl-2-(naphthalen-1-yl)-6-(naphthalen-1-yl)benzenesulfonate (labeled as aCSO5), was investigated using optical rotatory dispersion (ORD), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) spectroscopies. All three methods led to the same conclusion and the AC of aCSO5 is reliably determined to be (-)-(aR, aR), or conversely (+)-(aS, aS).

Keywords: FRULIC-n; chiral separation; chiroptical spectra; dissymmetry factor; quantum chemical prediction; similarity overlap.

MeSH terms

Circular Dichroism
Models, Molecular
Molecular Conformation
Naphthalenes / chemistry*
Optical Rotatory Dispersion
Stereoisomerism
Sulfonic Acids / chemistry*
Vibration*

Substances

Naphthalenes
Sulfonic Acids