Struktur Dan Kajian Spektroskopi Terbitan Metilbenzoilthiourea

Translated title of the contribution: Structural and spectroscopic studies of novel methylbenzoylthiourea derivatives

Rabia'tun Hidayah Jusoh, Wan M. Khairul, M. Sukeri M Yusof, Maisara Abdul Kadir, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Three new compounds, N-(2-methybenzoyl)-N'-(3-methyl-2-pyridyl)thiourea (I), N-(3-methylbenzoyl)-N'-(6-methyl-2-pyridyl)thiourea (II) are isomers and N-(2-methylbenzoyl)-N'-(6-methylpyridine-2-yl)thione (III) have been successfully synthesised and characterised by typical spectroscopic techniques, IR, UV-Visible, 1H and 13C Nuclear Magnetic Resonance (NMR) and CHNS analysis. The molecular structures were confirmed by single crystal X-ray diffractometer analysis. The Infrared spectra of these compounds showed four significant stretching vibrations, v(N-H), v(C=O), v(C-N) and v(C=S) at 3187-3375 cm-1, 1683-1713 cm-1, 1326-1384 cm-1 and 666-785 cm-1, respectively. The UV-Visible spectra of all compounds show three bands obtained in the range of 205-287 nm, which may be due to n→π* and π→π* transitions. In 13C NMR spectra, the signal of carbon carbonyl for (I) and (II) can be observed at ca. δc 170 ppm. Whilst, chemical shift of the carbon thione groups for (I) and (II) appeared at ca. 180 ppm. Molecule (I), (II) and (III) crystallise in the monoclinic crystal system with space group P21/n. Molecule (I) adopts trans-cis configuration in comparison with II which adopts cis-trans configuration of the pyridine and methylbenzoyl groups with respect to the thione S atom across the thiourea C-N bonds. However, (III) is planar due to cyclisation forming two five-membered rings. All molecules are stabilised by intra-molecular hydrogen bonds, N-H...O, C-H...N, N-H...N and C-H...O lead to the formation of pseudo seven-membered rings (I) and pseudo six-membered (II & III) rings. In the crystal lattice, molecule (I) are linked by the N-H...O, C-H...S and N-H...S (II) inter-molecular hydrogen bonds, whilst for (III), there are no inter-molecular hydrogen bond was observed.

Original languageUndefined/Unknown
Pages (from-to)70-80
Number of pages11
JournalMalaysian Journal of Analytical Sciences
Volume15
Issue number1
Publication statusPublished - 2011

Fingerprint

Thiones
Thiourea
Derivatives
Hydrogen bonds
Molecules
Carbon
Nuclear magnetic resonance
Cyclization
Diffractometers
Chemical shift
Crystal lattices
Isomers
Molecular structure
Stretching
Single crystals
Infrared radiation
X rays
Atoms
Crystals

Keywords

  • Carbonylthiourea
  • Methylbenzoylthiourea
  • Spectroscopic studies
  • Thiourea

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

Jusoh, R. H., Khairul, W. M., Yusof, M. S. M., Kadir, M. A., & Mohd. Yamin, B. (2011). Struktur Dan Kajian Spektroskopi Terbitan Metilbenzoilthiourea. Malaysian Journal of Analytical Sciences, 15(1), 70-80.

Struktur Dan Kajian Spektroskopi Terbitan Metilbenzoilthiourea. / Jusoh, Rabia'tun Hidayah; Khairul, Wan M.; Yusof, M. Sukeri M; Kadir, Maisara Abdul; Mohd. Yamin, Bohari.

In: Malaysian Journal of Analytical Sciences, Vol. 15, No. 1, 2011, p. 70-80.

Research output: Contribution to journalArticle

Jusoh, RH, Khairul, WM, Yusof, MSM, Kadir, MA & Mohd. Yamin, B 2011, 'Struktur Dan Kajian Spektroskopi Terbitan Metilbenzoilthiourea', Malaysian Journal of Analytical Sciences, vol. 15, no. 1, pp. 70-80.
Jusoh RH, Khairul WM, Yusof MSM, Kadir MA, Mohd. Yamin B. Struktur Dan Kajian Spektroskopi Terbitan Metilbenzoilthiourea. Malaysian Journal of Analytical Sciences. 2011;15(1):70-80.
Jusoh, Rabia'tun Hidayah ; Khairul, Wan M. ; Yusof, M. Sukeri M ; Kadir, Maisara Abdul ; Mohd. Yamin, Bohari. / Struktur Dan Kajian Spektroskopi Terbitan Metilbenzoilthiourea. In: Malaysian Journal of Analytical Sciences. 2011 ; Vol. 15, No. 1. pp. 70-80.
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abstract = "Three new compounds, N-(2-methybenzoyl)-N'-(3-methyl-2-pyridyl)thiourea (I), N-(3-methylbenzoyl)-N'-(6-methyl-2-pyridyl)thiourea (II) are isomers and N-(2-methylbenzoyl)-N'-(6-methylpyridine-2-yl)thione (III) have been successfully synthesised and characterised by typical spectroscopic techniques, IR, UV-Visible, 1H and 13C Nuclear Magnetic Resonance (NMR) and CHNS analysis. The molecular structures were confirmed by single crystal X-ray diffractometer analysis. The Infrared spectra of these compounds showed four significant stretching vibrations, v(N-H), v(C=O), v(C-N) and v(C=S) at 3187-3375 cm-1, 1683-1713 cm-1, 1326-1384 cm-1 and 666-785 cm-1, respectively. The UV-Visible spectra of all compounds show three bands obtained in the range of 205-287 nm, which may be due to n→π* and π→π* transitions. In 13C NMR spectra, the signal of carbon carbonyl for (I) and (II) can be observed at ca. δc 170 ppm. Whilst, chemical shift of the carbon thione groups for (I) and (II) appeared at ca. 180 ppm. Molecule (I), (II) and (III) crystallise in the monoclinic crystal system with space group P21/n. Molecule (I) adopts trans-cis configuration in comparison with II which adopts cis-trans configuration of the pyridine and methylbenzoyl groups with respect to the thione S atom across the thiourea C-N bonds. However, (III) is planar due to cyclisation forming two five-membered rings. All molecules are stabilised by intra-molecular hydrogen bonds, N-H...O, C-H...N, N-H...N and C-H...O lead to the formation of pseudo seven-membered rings (I) and pseudo six-membered (II & III) rings. In the crystal lattice, molecule (I) are linked by the N-H...O, C-H...S and N-H...S (II) inter-molecular hydrogen bonds, whilst for (III), there are no inter-molecular hydrogen bond was observed.",
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