The Malaysian Journal of Analytical Sciences Vol 15 No 1 (2011): 70 -80

 

 

 

STRUCTURAL AND SPECTROSCOPIC STUDIES OF NOVEL METHYLBENZOYLTHIOUREA DERIVATIVES

 

Rabia’tun Hidayah Jusoh¹, Wan M. Khairul ¹, M. Sukeri M. Yusof^1*, Maisara Abdul Kadir¹,  Bohari M.Yamin²

 

¹Department of Chemical Sciences,

Faculty of Science and Technology,

Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia.

²School of Chemical Sciences and Food Technology,

Faculty of Science and Technology,

Universiti Kebangsaan Malaysia, 43650 Bangi, Selangor, Malaysia.

 

 *Corresponding author: mohdsukeri@umt.edu.my

 

 

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, n(N-H), n(C=O), n(C-N) and n(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.

 

Keywords: Methylbenzoylthiourea, carbonylthiourea, thiourea, spectroscopic studies

 

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