A DFT analysis of the molecular structures and vibrational spectra of 4,4′-sulfonyldiphenol

We have studied the structural properties and vibrational spectra of Bisphenol S (4,4′-sulfonyldi-phenol) with the help of Density Functional Calculations using a 6-311G** basis set. In addition we recorded experimental spectra in our laboratory. With the help of the GaussView program we could provide a complete assignment of the vibrational lines to the calculated normal modes of the molecule. The calculated and experimental vibrational spectra agree rather well with each other and we found the properties of Bisphenol S to be rather similar to the sulfa drug dapsone studied earlier. Interestingly, the electron donating power of an OH aubstituent at a phenyl ring seems to be less effective than that of an NH ₂ (in dapsone) substituent, because in Bisphenol S the relative intensity of the ring breathing line in the Raman spectrum appears to be much larger than in dapsone. We reach this conclusion about the electron donating powers of susbtituents, because in an early study on chlorine substituted anilines we have found that the larger the electron density in the ring becomes, the more the relative intensity of that line diminishes.