Sulfonamides as a subject to study molecular interactions in crystals and solutions: Sublimation, solubility, solvation, distribution and crystal structure

Crystal structures of 4-amino-N-(4-chlorophenyl)-benzene-sulfonamide (IV), 4-amino-N-(2,3-dichlorophenyl)-benzene-sulfonamide (V), 4-amino-N-(3,4-dichlorophenyl)-benzene-sulfonamide (VI) and 4-amino-N-(2,5-dichlorophenyl)-benzene-sulfonamide (VII) were solved by X-ray diffraction method. Temperature dependencies of saturated vapour pressure and thermodynamic functions of sublimation process were calculated (IV: ΔGsub298=74.0 kJ mol−1, ΔHsub298=134.1±1.2 kJ mol−1, ΔSsub298=202±3 J mol−1 K−1; V: ΔGsub298=61.7 kJ mol−1, ΔHsub298=141.1±0.7 kJ mol−1, ΔSsub298=266±2 J mol−1 K−1; VI: ΔGsub298=85.8 kJ mol−1, ΔHsub298=167.5±3.6 kJ mol−1, ΔSsub298=274±8 J mol−1 K−1; VII: ΔGsub298=75.7 kJ mol−1, ΔHsub298=155.4±1.6 kJ mol−1, ΔSsub298=268±4 J mol−1 K−1). Thermochemical parameters of fusion and evaporation processes for the compounds were obtained. Temperature dependencies of the solubility in water, n-octanol were measured. The thermodynamic functions of solubility and solvation processes were deduced. The transfer processes of the molecules from water to n-octanol were analysed by diagram method and main driven forces were established.