The Malaysian Journal of Analytical Sciences Vol 15 No 1 (2011): 37 – 45

 

 

 

SPECTROSCOPIC AND STRUCTURAL STUDY OF A SERIES OF PIVALOYLTHIOUREA DERIVATIVES

 

Siti Aishah Zakaria1, Siti Hajar Muharam1, Mohd Sukeri Mohd Yusof1,3*, Wan Mohd Khairul1,

Maisara Abdul Kadir1 & Bohari M. Yamin2

 

1Department of Chemical Sciences, Faculty of Science and Technology,

Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu.

2School of Chemical Sciences and Food Technology, Faculty of Science and Technology,

Universiti Kebangsaan Malaysia, 43650 Bangi, Selangor.

3Institue of Marine Biotechnology,

Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu.

 

*Corresponding author: mohdsukeri@umt.edu.my

 

 

Abstract

A series of pivaloylthiourea derivatives, N-(2-nitrophenyl)-N˘-(pivaloyl)thiourea (I), N-(3-nitrophenyl)-N˘-(pivaloyl)thiourea (II) and N-(4-nitrophenyl)-N˘-(pivaloyl)thiourea (III) were synthesised and characterised by typical spectroscopic methods and single crystal X-ray diffraction. The IR spectra show the important  stretching bands for ν(N-H), ν(C=O), ν(C-N) and ν(C=S) at around 3300 cm-1, 1600 cm-1, 1300 cm-1 and 700 cm-1, respectively. There are two vital chromophores, C=O and C=S were observed in the UV spectra with maximum absorption at 230 nm and 290 nm, respectively. The crystal structures of (II) and (III) have been determined by single crystal X-ray diffraction analysis. Both of the molecules adopt cis-trans configuration with respect to the position of the phenyl and pivaloyl groups relative to the thiono S atom, across their C-N bonds. There is an intramolecular hydrogen bond, N-H...O in both molecules that lead to the formation of a pseudo-six-membered ring. In the crystal lattice, the molecules are linked by intermolecular hydrogen bonds N-HS, C-HS and N-HO forming dimer (II) and 3-dimensional network (III). 1H NMR spectra show chemical shift at δH 12.70 – 12.88 ppm and δH 10.84 – 10.94 ppm were assigned for both NH proton. Whereas, the chemical shift for 13C NMR analysis for C=O and C=S presence at δC 179-180 ppm.

 

Keywords: Thiourea derivatives, Pivaloylthiourea, Crystal structure.

 

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