Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

Fatma Aydin,N Burcu Arslan

doi:10.3390/m1316

Abstract

Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental analysis and FT-IR, 1H, and 13C-NMR spectroscopic methods. The crystal structure of the title compound 1 was determined by an X-ray single-crystal technique and an intramolecular C=O…H-N hydrogen bond and intermolecular C=S…H-N and C=S…H-C hydrogen interactions, which were observed for the crystal structure. The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted. Cyclic voltammetric (CV) experiments for the compounds were performed with the glassy carbon electrode. The reduction in potential values of the different functional groups such as nitro and cyano in title compounds were investigated using CV curves.

Highlights

N-(aroyl/acyl)-N 0 -substituted-(aryl/alkyl)-thiourea derivatives are known to exhibit a wide variety of biological activities such as antibacterial and antifungal properties and regulating activities for plant protection in agriculture [1,2,3]
Some aroylthioureas were used in the synthesis of benzoylaminoimidazolone and aminoimidazolone derivatives [11], bicyclic 2-aminothiazolyl compounds [12] and some tetrazoles and guanidines [13]
The molecular conformation is stable by an intramolecular N-H...O hydrogen bond and intermolecular

Summary

Introduction

N-(aroyl/acyl)-N 0 -substituted-(aryl/alkyl)-thiourea derivatives are known to exhibit a wide variety of biological activities such as antibacterial and antifungal properties and regulating activities for plant protection in agriculture [1,2,3]. Some of them have been used as ligands in the extraction, separation, and determination of heavy metals such as Fe and Zn ions [4,5] These types of ligands have been used as a chemosensor for anions such as F− , CN− , OAc− , etc., and as a potentiometric sensor for heavy metals in analytical applications [6,7]. The synthesis of biologically important heterocyclic scaffolds, such as thiohydantoins has been used some arylthiourea derivatives [10]. Some aroylthioureas were used in the synthesis of benzoylaminoimidazolone and aminoimidazolone derivatives [11], bicyclic 2-aminothiazolyl compounds [12] and some tetrazoles and guanidines [13]

Methods

Results

Conclusion