Synthesis, X-Ray, spectroscopic characterization (FT-IR, NMR, UV–Vis) and quantum chemical calculations of some substituted benzoylthiourea derivatives

Hamza M. Abosadiya, El Hassane Anouar, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

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 1a-4a are elucidated by FT-IR, UV–Vis, 1H and 13C NMR spectroscopic techniques. The four benzoylthiourea derivatives were obtained in crystalline forms by recrystallization in DMSO. X-ray chemical crystallographic study shows that 1a 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 1a-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.

Original languageEnglish
Pages (from-to)48-56
Number of pages9
JournalJournal of Molecular Structure
Volume1194
DOIs
Publication statusPublished - 15 Oct 2019

Fingerprint

Thiourea
Nuclear magnetic resonance
Derivatives
Discrete Fourier transforms
X rays
Bearings (structural)
Phenylthiourea
Crystals
Condensation reactions
Pulse code modulation
Dimethyl Sulfoxide
Molecular structure
Crystallization
Crystalline materials
Molecules

Keywords

  • DFT
  • N-(4-methoxybenzoyl)-N`-(3-hydroxyphenyl)thiourea
  • NMR
  • TD-DFT
  • Thiourea derivatives
  • X-ray

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Synthesis, X-Ray, spectroscopic characterization (FT-IR, NMR, UV–Vis) and quantum chemical calculations of some substituted benzoylthiourea derivatives. / Abosadiya, Hamza M.; Anouar, El Hassane; Mohd. Yamin, Bohari.

In: Journal of Molecular Structure, Vol. 1194, 15.10.2019, p. 48-56.

Research output: Contribution to journalArticle

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AB - 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 1a-4a are elucidated by FT-IR, UV–Vis, 1H and 13C NMR spectroscopic techniques. The four benzoylthiourea derivatives were obtained in crystalline forms by recrystallization in DMSO. X-ray chemical crystallographic study shows that 1a 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 1a-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.

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