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

• Published in: International journal of pharmaceutics Vol. 349; no. 1; pp. 300 - 313
• Main Authors: Perlovich, German L., Strakhova, Nadezda N., Kazachenko, Vladimir P., Volkova, Tatyana V., Tkachev, Valery V., Schaper, Klaus-Jurgen, Raevsky, Oleg A.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 12.02.2008; Elsevier
• Subjects: 4-Amino- N-(2,3-dichlorophenyl)-benzene-sulfonamide; 4-Amino- N-(2,5-dichlorophenyl)-benzene-sulfonamide; 4-Amino- N-(3,4-dichlorophenyl)-benzene-sulfonamide; 4-Amino- N-(4-chlorophenyl)-benzene-sulfonamide; Algorithms; Calorimetry, Differential Scanning; Crystal structure; Crystallization; Hydrogen Bonding; Models, Molecular; Molecular Conformation; Pharmaceutical Solutions; Solubility; Solvation; Solvents; Sublimation thermodynamics; Sulfonamides - chemistry; Temperature; Thermodynamics; Transfer process; X-Ray Diffraction; Transfer process; 4-Amino- N-(3,4-dichlorophenyl)-benzene-sulfonamide; Solvation; Sublimation thermodynamics; Solubility; 4-Amino- N-(4-chlorophenyl)-benzene-sulfonamide; 4-Amino- N-(2,5-dichlorophenyl)-benzene-sulfonamide; 4-Amino- N-(2,3-dichlorophenyl)-benzene-sulfonamide; Crystal structure
• ISSN: 0378-5173; 1873-3476
• DOI: 10.1016/j.ijpharm.2007.07.034

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.