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

AGUILAR, E. CONTRERAS; COGOLLO, E. ESPITIA; ECHEVERRÍA, G.A.; PIRO, O.E.; JIOS, J.L.; ULIC, S.E.; MOLINA, R.D.I.; ARENA, M.E.

NEW JOURNAL OF CHEMISTRY

ROYAL SOC CHEMISTRY

Año: 2023 vol. 47 p. 18341 - 18353

1144-0546

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.