Preferential solvation of thiophene and furan-2-carboxaldehyde phenylhydrazone derivatives in DMSO-water and DMSO-n-octanol mixtures

Abstract

The preferential solvation of thiophene- and furan-2-carboxaldehyde phenylhydrazone derivatives in DMSO-water and DMSO-n-octanol mixtures has been studied using visible absorption spectroscopy with a previous characterization of the electronic transitions by Time-Dependent Density Functional Theory (TDDFT) and solvatochromic study in several solvents with different hydrogen-bond donor capacity. The results indicate that the phenylhydrazones are preferentially solvated by clusters of DMSO-water existing in the solvent mixture and the dielectric enrichment as preferential solvation mechanism was discarded. A relation between local DMSO concentration with nitro groups and the electronegativity of the heteroatom of the five-membered ring was found. For DMSO-1-octanol mixtures, the results showed no preferential solvation.