作为研究晶体和溶液中分子相互作用的对象的磺胺类药物：升华、溶解度、溶剂化作用、分布和晶体结构。

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

作者信息

Perlovich German L, Strakhova Nadezda N, Kazachenko Vladimir P, Volkova Tatyana V, Tkachev Valery V, Schaper Klaus-Jurgen, Raevsky Oleg A

机构信息

Department of Computer-Aided Molecular Design, Institute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Russia.

出版信息

Int J Pharm. 2008 Feb 12;349(1-2):300-13. doi: 10.1016/j.ijpharm.2007.07.034. Epub 2007 Aug 2.

DOI:10.1016/j.ijpharm.2007.07.034

PMID:17913412

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: delta Gsub298=74.0 kJ mol(-1), delta Hsub298=134.1+/-1.2 kJ mol(-1), delta Ssub298=202+/-3 J mol(-1)K(-1); V: delta Gsub298=61.7 kJ mol(-1), delta Hsub298=141.1+/-0.7 kJ mol(-1), delta Ssub298=266+/-2 J mol(-1)K(-1); VI: delta Gsub298=85.8 kJ mol(-1), delta Hsub298=167.5+/-3.6 kJ mol(-1), delta Ssub298=274+/-8 J mol(-1)K(-1); VII: delta Gsub298=75.7 kJ mol(-1), delta Hsub298=155.4+/-1.6 kJ mol(-1), delta Ssub298=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.

摘要

通过X射线衍射法解析了4-氨基-N-(4-氯苯基)-苯磺酰胺(IV)、4-氨基-N-(2,3-二氯苯基)-苯磺酰胺(V)、4-氨基-N-(3,4-二氯苯基)-苯磺酰胺(VI)和4-氨基-N-(2,5-二氯苯基)-苯磺酰胺(VII)的晶体结构。计算了饱和蒸气压的温度依赖性和升华过程的热力学函数(IV: ΔGsub298 = 74.0 kJ mol⁻¹, ΔHsub298 = 134.1±1.2 kJ mol⁻¹, ΔSsub298 = 202±3 J mol⁻¹K⁻¹; V: ΔGsub298 = 61.7 kJ mol⁻¹, ΔHsub298 = 141.1±0.7 kJ mol⁻¹, ΔSsub298 = 266±2 J mol⁻¹K⁻¹; VI: ΔGsub298 = 85.8 kJ mol⁻¹, Δ ΔHsub298 = 167.5±3.6 kJ mol⁻¹, ΔSsub298 = 274±8 J mol⁻¹K⁻¹; VII: ΔGsub298 = 75.7 kJ mol⁻¹, ΔHsub298 = 155.4±1.6 kJ mol⁻¹, ΔSsub298 = 268±4 J mol⁻¹K⁻¹)。获得了这些化合物熔融和蒸发过程的热化学参数。测量了它们在水中、正辛醇中的溶解度随温度的变化。推导了溶解度和溶剂化过程的热力学函数。用图解法分析了分子从水到正辛醇的转移过程，并确定了主要驱动力。