Abstract
Thiabendazole (TBZ) is a substance which has been receiving multiple important applications in several domains, from medicine and pharmaceutical sciences, to agriculture and food industry. Here, a comprehensive multi-technique investigation on the molecular and crystal properties of TBZ is reported. In addition, a new solvate of the compound is described and characterized structurally, vibrationally and thermochemically for the first time. Density functional theory (DFT) calculations were used to investigate the conformational space of thiabendazole (TBZ), revealing the existence of two conformers, the most stable planar trans form and a double-degenerated-by-symmetry gauche form, which is ~30 kJ mol−1 higher in energy than the trans conformer. The intramolecular interactions playing the major roles in determining the structure of the TBZ molecule and its conformational preferences were characterized. The UV-visible and infrared spectra of the isolated molecule (most stable trans conformer) were also calculated, and their assignment undertaken. The information obtained for the isolated molecule provided a strong basis for the understanding of the intermolecular interactions and properties of the crystalline compound. In particular, the infrared spectrum for the isolated molecule was compared with that of crystalline TBZ and the differences between the two spectra were interpreted in terms of the major intermolecular interactions existing in the solid state. The analysis of the infrared spectral data was complemented with vibrational results of up-to-date fully-periodic DFT calculations and Raman spectroscopic studies. The thermal behavior of TBZ was also investigated using differential scanning calorimetry (DSC) and thermogravimetry. Furthermore, a new TBZ–formic acid solvate [2-(1,3-thiazol-4-yl)benzimidazolium formate formic acid solvate] was synthesized and its crystal structure determined by X-ray diffraction. The Hirshfeld method was used to explore the intermolecular interactions in the crystal of the new TBZ solvate, comparing them with those present in the neat TBZ crystal. Raman spectroscopy and DSC studies were also carried out on the solvate to further characterize this species and investigate its temperature-induced desolvation.
Highlights
Thiabendazole (TBZ; C10H7N3S; IUPAC name: 4-(1H-1,3-benzodiazol-2-yl)-1,3-thiazole; Scheme1) is an organic chemical compound derived from benzimidazole and thiazole
Structural Details differences in the intramolecular interactions in the inter-rings region of the molecule lead to According to the B3LYP/6-311++G(2d,2p) calculations, TBZ exhibits two conformers, a planar larger angles associated with the H-C2-C3-C4-N3-H pseudo-ring in the gauche conformer, as welltoastwo in the longer C3-C4 bond length
The repulsive interactions between the atoms closely located to the C3-C4 inter-rings bond in the gauche conformer vs. the attractive ones in the trans conformer were found to be the intramolecular interactions playing the major roles in determining the differences in the geometries of the two thiabendazole conformers as well as their relative energy
Summary
Thiabendazole (TBZ; C10H7N3S; IUPAC name: 4-(1H-1,3-benzodiazol-2-yl)-1,3-thiazole; Scheme. 1) is an organic chemical compound derived from benzimidazole and thiazole Brown et al reported that the compound, prepared by the reaction of Thiabendazole 4-thiazolecarboxamide with o-phenylenediamine, a polyphosphoric acid catalyst, exhibited is an organic chemical compound derived from using benzimidazole and thiazole. It firstly gained broad spectrum anti-helminthic activity [1,2]. TBZ is rapidly absorbed upon ingestion, and the peak commercial importance when Brown et al reported that the compound, prepared by the reaction plasma concentration is reached within 1 to 2 hours after the oral administration of a suspension. If the recommended dose is not exceeded, the compound has no harmful effects on the body, plasma concentration is reached within 1 to 2 hours after the oral administration of a suspension
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