N,N-(2,3-Dimethylbut-2-ene-1,4-dienyl)dibenzenesulfonamide and N,N '-(2E)-2,3-Dimethylbut-2-ene-1,4-dienylbis(trifluoroacetamide): Special Features of Hydrogen Bonding in the Crystal and Solutions

摘要

The types of intermolecular self-associates of N,N-(2,3-dimethylbut-2-ene-1,4-diyl)dibenzenesulfonamide and N,N '-[(2E)-2,3-dimethylbut-2-ene-1,4-diyl]bis(trifluoroacetamide) formed in CCl4 solutions via hydrogen bonding have been studied by means of IR spectroscopy and quantum chemistry methods [B3LYP/6-311G(d,p)]. The obtained data have been compared to the X-ray diffraction analysis data. The benzenesulfonamide derivative forms strong hydrogen-bonded tetramers, which exist in the crystal as well as in solution, while the self-associates of the trifluoroacetamide derivative are linked by weaker H-bonds, which are readily broken in solution upon dilution.