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 Yusof^1,3*, 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-H^…S, C-H^…S and N-H^…O forming dimer (II) and 3-dimensional network (III). ¹H NMR spectra show chemical shift at δ_H 12.70 – 12.88 ppm and δ_H 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 δ_C 179-180 ppm.

 

Keywords: Thiourea derivatives, Pivaloylthiourea, Crystal structure.

 

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