Integrated intensities of hydroxy stretching vibration bands in some bicyclic systems containing a hydroxy group β to o-benzeno, etheno, epoxy, or epithio functions

Abstract

For the title class of compounds, OH stretching vibration bands, ν_OH, and integrated, intensities, A_OH, were measured for dilute carbon tetrachloride solutions. When A_OH values were compared for f-structures which are incapable of intramolecular hydrogen bonding and b-structures in which intramolecular bonding takes place, the result was remarkable in that the A_OH values of free ν_OH bands in f-structures were greater than those for the hydrogen-bonded ν_OH bands in the b-structures. The CO and C–O stretching vibration bands, ν_CO and ν_C–O, for the corresponding acetates were also measured. The ν_CO bands for the f-structures shifted to higher wavenumbers than those for b-structures, but the ν_C–O bands are shifted to lower wavenumbers. These results were ascribed to the through-space interaction between π- or n-electrons and the sp³-hybridized carbon atom bearing hydroxy and acetoxy groups which affects on polarization of these groups.