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Title:	Synthesis, characterization, structural and biological studies of some subtituted phenylthioureas and pyrimidinethione derivatives
Authors:	Halima Farag Salem (P48963)
Supervisor:	Bohari M. Yamin, Prof. Dr.
Keywords:	Universiti Kebangsaan Malaysia -- Dissertations Thiourea-Synthesis Pyrimidines Dissertations, Academic -- Malaysia
Issue Date:	27-Sep-2012
Description:	Ten new phenylthioureas namely phenylthiourea (I), o-fluorophenylthiourea (II), m-fluorophenylthiourea(III), p-fluorophenylthiourea(IV), o-chlorophenylthiourea (V), m-chlorophenylthiourea(VI),o-bromophenylthiourea(VII) m-bromophenylthiourea(VIII), p-bromophenylthiourea(IX) and N-methyl-N'-phenylthiourea (X) have been synthesized from the reaction of thiocyanic acid with substituted aniline in acetonitrile as solvent. The compounds were characterized by microelemental analysis, infrared, nuclear magnetic resonance and ultra violet-visible spectroscopic techniques. A mechanism involving a nucleophilic attack of amine base to the carbon of the thiocyanic acid followed by electronic and hydrogen rearrangement to form the thiourea moiety is presented. X-ray investigation has shown that all the compounds crystallized in different crystal systems. Intermolecular hydrogen bonds play the important role for their stabilities in the solid state that led for the formation of two-dimensional network or one-dimensional chain. However, the same reaction, but in acetone gave cyclic 1-(X-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione derivatives where X= Cl, Br, F and NO2. The structures of the eight pyrimidinethione derivatives were supported by microelemental analysis, infrared, nuclear magnetic resonance and ultraviolet- visible spectroscopic techniques. The X-ray structures of all the pyrimidinethione derivatives were obtained. All the pyrimidinethione derivatives crystallized in monoclinic system with different space groups. The reaction of thiocyanic acid with p-chloroaniline did not give the analogous products, but instead p-chloroanilinium thiocyanate was formed. On the other hand, the reaction of 1, 2-diaminocyclohexane with thiocyanic acid gave 2-aminocyclohexan-1-aminium thiocyanate. The complexation of cobalt and copper with o-fluorophenylthiourea, p-fluorophenylthiourea and m-chlorophenylthiourea gave salt type complexes with the formula of [Cu (SO4) (C7H7FN2S)2.H2O], [Cu (C7H7F N2S)4]Cl2 and [Co (C7H7Cl N2S)6 ]Cl2 respectively. Antibacterial study of the substituted phenylthiourea against Gram positive (Bacillus subtilis, Staphylococcus aureus and Staphylococcus epidermidis) and Gram negative (Salmonella typhimurium, Pseudomonas aeruginosa, Enterobacter aerogenes, and Escherichia coli) bacteria indicate that the m-fluorophenylthiourea showed significant activity compared with the other phenylthioureas,Certification of Master's/Doctoral Thesis" is not available
Pages:	264
Call Number:	QD315.S235
Publisher:	UKM, Bangi
Appears in Collections:	Faculty of Science and Technology / Fakulti Sains dan Teknologi

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