Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate

Abstract

The dissymmetric compound C 21 H 17 N 3 O 2 S.0.5H 2 O obtained by a reaction of 1,2-diaminobenzene, potassium thiocyanate and benzoyl chloride in 1/1/2 ratio is characterized by elemental analyses, IR, and NMR spectroscopies. The structure is elucidated by X-ray diffraction technic. The compound crystallizes in the monoclinic system with a space group of I2. The asymmetric unit contains one hemihydrate organic molecule. The title thiourea derivative, features an almost planar, C 2 N 2 S (S1/N1/N2/C7/C8) moiety, with a maximum deviation from the least-squares plane of 0.0422 (3) Å. This moiety is flanked by a disubstituted and a monosubstituted phenyl rings. The dihedral angles between the thiourea and the monosubstituted phenyl ring and the thiourea and the central disubstituted phenyl ring are respectively 10.418 (7)° and 60.292 (2)°, indicating twist in the molecule. On the other arm, a phenyl ring supported by an amide function, which is linked to the central ring through the nitrogen atom, is present. The dihedral angle between this phenyl group and the central disubstituted phenyl is 76.862 (7)° showing that their mean planes are not coplanar. Intramolecular S(thiono)-H…O(water) hydrogen bonds which close in S(6) and S(7) rings consolidate the conformation. Intermolecular N(amido)-H…O(carbonyl) which form layers parallel to the ac plane stabilized the structure.

Synthesis, Anti-breast Cancer Activity, and Molecular Docking Studies of Thiourea Benzamide Derivatives and Their Complexes with Copper Ion

“…11 The signals with the range 121.73-150.79 ppm are attributed to the aromatic carbons, and the signal at 21.19 ppm in L4 spectra is attributed to the aliphatic carbons (CH3). 22 The infrared spectra for prepared compounds showed medium and strong intensity bands at a range of 3442-3107 cm -1 assigned to the (N-H) group's stretching vibration. This indicates the formation of ligands, and one or two bands at the range between 3097-3016 cm -1 were observed due to symmetrical and asymmetrical stretching vibration of (C-H) aromatic for both ligands and complexes.…”

“…1 HNMR spectra of ligands (Figure 1) showed singlet, doublet, and multiplet signals at the range of 7.25-8.80 ppm which can be attributed to aromatic protons. 22 The appearance of a singlet signal in the spectra confirmed the presence of the amide group (-NH) at 9.20, 9.28, 9.20, 9.22, and 9.24 ppm for L1, L2, L3, L4, and L5 respectively, while the (-NH) group's proton signal showed up as a singlet at 12.90, 12.76, 12.84, 12.27, and 12.40 ppm. 23 The spectra of ligand L4 showed a singlet signal at 2.38 due to (-CH3) protons.…”

Synthesis and crystal structures of two related Co and Mn complexes: a celebration of collaboration between the universities of Dakar and Southampton

“…This activity enabled considerable knowledge transfer to LCCO and subsequently, more than 70 further sample analyses have been successfully completed. Many novel and interesting structures have been characterized and have resulted in eleven joint publications in a range of journals, between 2018 and 2023 (Gaye et al, 2018(Gaye et al, , 2020Gaye, Fall et al, 2023;Gaye, Sarr et al, 2023;Gaye, Ndoye et al, 2021;Gaye, Kebe et al, 2021;Sokhna et al, 2023); Diallo et al, 2022;Diop et al, 2019;Faye et al, 2020;Sarr et al, 2018;Sylla-Gueye et al, 2020). Recent samples originated from more than a dozen current doctoral students from within the LCCO itself, the wider Department of Chemistry or from two additional joint projects with the University of Bambey, Senegal and Gaston Berger University of Saint-Louis, Senegal.…”