Publication: Synthesis, X-Ray, spectroscopic characterization (FT-IR, NMR, UV-Vis) and quantum chemical calculations of some substituted benzoylthiourea derivatives
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Date
2019
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Publisher
Elsevier Science BV
Abstract
A new series of substituted benzoylthiourea derivatives namely N-(4-methoxybenzoyl)-N'-(3-hydroxyphenyl)thiourea (1a), N-(3-methoxybenzoyl)-N'-(3-hydroxyphenyl) thiourea (2a), N-(3-nitrobenzoyl)-N'-(3-hydroxyphenyl)thiourea (3a) and N-(4-phenylbenzoyl)-N'-(3-hydroxy phenyl) thiourea (4a) bearing phenolic groups were efficiently synthesized from the condensation reaction of benzoylisothiocyanate with 3-aminophenol. The molecular structures of la-4a are elucidated by FT-IR, UV-Vis, H-1 and C-13 NMR spectroscopic techniques. The four benzoylthiourea derivatives were obtained in crystalline forms by recrystallization in DMSO. X-ray chemical crystallographic study shows that la crystallizes in triclinic crystal system, while 2a-4a crystalize in monoclinic crystal system. The synthesized benzoylthiourea molecules adopt trans cis configuration with respect to the positions of carbonoylbenzoyl and 3-hydroxyphenyl groups respectively, against the thiono C=S bonds across their C -N bonds. The corresponding predicted z-matrix coordinates and spectral data of la-4a were obtained using DFT and TD-DFT methods. The quantum chemical calculation have been carried out using three hybrid functionals B3LYP, B3P86 and PBE0 combined with 6-31++G(d,p) basis set. The solvent effects were taken into account implicitly using IEF-PCM model. The experimental Z-matrix coordinates and the spectral data of the tilted compounds are relatively well reproduced with good correlations coefficients. (C) 2019 Elsevier B.V. All rights reserved.
Description
Journal of Molecular Structure
Volume 1194, 15 October 2019, Pages 48-56
Keywords
Thiourea derivatives, N-(4-methoxybenzoyl)-N '-(3-hydroxyphenyl)thiourea, X-ray, NMR, DFT, TD-DFT