Synthesis, crystal and molecular structure of two biologically active aromatic sulfonamides and their hydrochloride salts

4-Sulfamoyl-N-(3-morpholinopropyl) benzamide (P10), N-(3-morpholinopropyl)benzene-1,4-disulfonamide (P20) and their hydrochloride salts (P11 and P22) were prepared. The X-ray molecular structure of these compounds was determined. The gas-phase structure of these drugs was computed using Becke3LYP/6-31G(d) and Becke3LYP/6-311 + G(d,p) model chemistries. The conformational behavior of these systems in water was examined using the solvation CPCM model. In the solid state, gas phase and in solution the conformations of the basic compounds P10 and P20 possess a characteristic L-shaped structure stabilized via an intramolecular hydrogen bonding system of the N-H center dot center dot center dot N type. This hydrogen bond is not present in P11 and P22. A network of intermolecular hydrogen bonds mediated by the Cl atoms and crystal-packing forces in P11 and P22 stabilize a more extended structure in the solid state. (C) 2010 Elsevier B.V. All rights reserved.