A vibrational circular dichroism approach to the determination of the absolute configuration of flexible and transparent molecules: fluorenoneketals of 1,n-diols

Abstract

The infrared absorption (IR) and vibrational circular dichroism (VCD) spectra for five ketal molecules, three of which obtained from 1,2-diols and two from 1,3-diols, were recorded in the mid-IR region. The spectra have been satisfactorily reproduced by DFT calculations, even with not too large wavefunction basis sets, especially due to the low number of conformers to be considered. The mobility of some moieties provides a recognizable signature. A characteristic couplet of VCD bands attributed to normal modes involving the methine and a phenyl ring bonded to the stereogenic carbon atom is evidenced for two ketals of the series as a signature of the absolute configuration; due comparison with existing literature is made. A relation is discussed of the present VCD data with the literature VCD data of simple alcohols and diols.