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

Abstract

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: Δ G sub 298 = 74.0 kJ mo l − 1 , Δ H sub 298 = 134.1 ± 1.2 kJ mo l − 1 , Δ S sub 298 = 202 ± 3 J mo l − 1 K − 1 ; V: Δ G sub 298 = 61.7 kJ mo l − 1 , Δ H sub 298 = 141.1 ± 0.7 kJ mo l − 1 , Δ S sub 298 = 266 ± 2 J mo l − 1 K − 1 ; VI: Δ G sub 298 = 85.8 kJ mo l − 1 , Δ H sub 298 = 167.5 ± 3.6 kJ mo l − 1 , Δ S sub 298 = 274 ± 8 J mo l − 1 K − 1 ; VII: Δ G sub 298 = 75.7 kJ mo l − 1 , Δ H sub 298 = 155.4 ± 1.6 kJ mo l − 1 , Δ S sub 298 = 268 ± 4 J mo l − 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.