The discrete role of chlorine substitutions in the conformation and supramolecular architecture of arylsulfonamides.

Two arylsulfonamide derivatives, N-(4-acetylphenyl)benzenesulfonamide, C(14)H(13)NO(3)S, and N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide, C(14)H(11)Cl(2)NO(3)S, differing by the absence or presence of two chloro substituents on one of the phenyl rings, were synthesized and characterized in order to establish structural relationships and the role of chloro substitution on the molecular conformation and crystal assembly. Both arylsulfonamides form inversion-related dimers through C-H···π and π-π interactions. These dimers pack in a similar way in the two structures.

Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic avenaciolide analogue.

Background: Avenaciolide, a natural product isolated from Aspergillus avenaceus H. Smith, possesses several interesting biological properties, such as antifungal and antibacterial activities and inhibition of glutamate transport in mitochondria. In a study aiming to discover new compounds with antifungal activity, a bis-gamma-lactone analogous to avenaciolide was prepared and characterized by elemental analysis, mass spectrometry, and infrared and NMR spectroscopy.