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

Fatou Faye,Simon Coles,Ibrahima Elhadji Thiam,Mohamed Gaye,James Orton,Rokhaya Sylla-Gueye

doi:10.11648/j.sjc.20200806.11

Abstract

The dissymmetric compound C21H17N3O2S.0.5H2O 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, C2N2S (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.

Highlights

Compounds derived from thiourea are molecules largely used in pharmaceutical industry for the preparation of heterocyclic derivatives
In the recent past we have started to study the coordination of some ligands derived from thiourea having a number of interesting properties. It is in this context that we have reported two thioureidos ligands whose two arms are bridged by ethane-1,2-diyl group [14] and 1,2-phenyl ring [15] respectively
We report the synthesis, the characterization and the X-ray structure of an asymmetric molecule in which a 1,2-phenyl ring bridges a thioureido group and an amido group yielding the compound (I)

Summary

Introduction

Compounds derived from thiourea are molecules largely used in pharmaceutical industry for the preparation of heterocyclic derivatives. Thiourea derivatives are reported as organic inhibitors for corrosion This property is due to the protonation of the sulfur atom in acidic medium [12, 13]. In the recent past we have started to study the coordination of some ligands derived from thiourea having a number of interesting properties. It is in this context that we have reported two thioureidos ligands whose two arms are bridged by ethane-1,2-diyl group [14] and 1,2-phenyl ring [15] respectively. We report the synthesis, the characterization and the X-ray structure of an asymmetric molecule in which a 1,2-phenyl ring bridges a thioureido group and an amido group yielding the compound (I)

Methods

Results

Conclusion