Isosteric O/S exchange in carbonyl(thio)ureides: molecular interactions, structure, and bioactivity assays

The solid-state molecular structures of N-(butylcarbamothioyl)-4-methoxybenzamide (I) and N-(butylcarbamoyl)-4-methoxybenzamide (II) were used as examples for structural analyses of carbonylthioureides and carbonylureides. Both compounds crystallize in the monoclinic P21/c space group and form nearly identical hydrogen-bonded dimeric aggregates. A thorough examination of intermolecular interactions using X-ray diffraction data, Hirshfeld surface analysis, molecular electrostatic potential maps, NBO and QTAIM approaches, and spectroscopic techniques reveals that the larger size of the sulfur atom has a significant impact on the strength and nature of the interactions within the crystal lattice. Furthermore, the isosteric exchange was evaluated by testing the activity of both compounds as antibiofilm and anti-quorum sensing agents. Structural study of carbonyl(thio)ureides and a comprehensive analysis on the intermolecular interactions that stabilize the crystal packing. Sulfur, rather than oxygen, promotes Quorum Sensing inhibition by reducing cell viability in a developed biofilm.