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Synthesis of Novel Macrocyclic From Schiff Bases Based on acetylacetone and terephtaldialdehide

تحضير مركبات حلقية ضخمة جديدة من أسس شيف أساسها أسيتيل اسيتون و تير فتال ثنائي ألدهيد

1938   0   11   0 ( 0 )
 Publication date 2010
and research's language is العربية
 Created by Shamra Editor




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macrocyclic hydrazone Schiff base was synthesized by reaction of succinicdihydrazide, Adipicdihydrazide with acetylacetone, adipicdihydrazide with terephtaldialdehide and sebacicdihydrazide with terephtaldialdehide.



References used
Avaji, P. G. Vinod Kumar, C. H. and Shivananda, K. N., 2009. Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone C. Eur. J. Med. Chem, V.xxx, pp.1-8
Popov, L. D. Tupolova, Yu. P. and Lukov, V. V., 2008. Transition metal complexes based on 2, 4-dihydroxyisophthalic anhydride and its functionalized derivative Russian J, V.78, pp. 2094- 2099
Pavan, F. P. Maia, P. S. Leite, S. R. A. and Deflon, V. M., 2010. Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: Anti – Mycobacterium tuberculosis activity and cytotoxicity. A. A. Eur J Med Chem, V. 45, pp. 1898-1905
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Imines based on different and secondary amines were synthesized by reaction of acetylacetone with 2-amino-5-nitro phenol, adamantine amine, 1.7- diamino heptane and o-aminophenol. 2.4-bis (2-hydroxy-4-nitro-1-imino phenyl) pentane, 2.4-bis (2-imin o admantyl) pentane, 2.4-bis(2hydrox y-1- iminophenyl) pentane and 1.5.13.18-tetraaza- 2.4.14.16- tetramethylcyclotetracosan- 1.4.13.16-tetraene have been characterized by EA, IR, 1HNMR and 13C-NMR.
This work was focused on the synthesis of tetradentate Schiff bases which were prepared by condensation of salicylaldehyde with 1,4-diaminobenzene and 1,3-diaminobenzene. The Schiff base ligands were checked by different spectral technique (GC-MS, 1H-NMR, IR). The influences of shaking time on the extraction of Cu (II) using solvent extraction technique was studied. Then the Kinitic parameters were calculated from schemes which give best line through drawing log (a-x) vs time or 1/(a-x) vs time or [Cu2+] vs time, whereas (a-x) represents Cu(II) concentration in water phase and from it (n) reaction order, (K) reaction rate constant (t1/2) reaction half between prepared ligand and Cu (II) were calculated.
Separation with solvent extraction of Cu(II), Hg(II), and Cr(III) from aqueous solution using the ligend (HL) as a new extractant has been studied. The new acyclic Schiff Base (HL) was synthesized by reaction of 5-bromosalicylaldehyde with 2-(2-Am inoethyl)pyridine. The structure of the new compound (HL) was confirmed by using FT-IR spectra, 1H-NMR and 13CNMR spectra and mass spectra (MS). The effect of chloroform and dichloromethan as organic solvents in the metal extractions was investigated at 20oC by using UV-visible Spectrometry. The influence of pH, ligand concentration, shaking time and ratio of aqueous-to-organic phases on extraction yield was tested at 20oC. The extractability of the tested metal ions were evaluated.
A new acyclic Schiff Base(II), containing nitrogen-oxygen donor atoms was synthesized by reaction of 1,2-Bis (5-bromo-2-formyl-phenoxy) ethane with 2- (2-Aminoethyl)pyridine and characterized. The liquid-liquid extraction of transition metals such as Cu+2, Cr+3 and Uranyl-picrate (UO2)+2 from aqueous phase to the organic phase was carried out using the novel ligand. The effect of chloroform and nitrobenzene as organic solvents on the metal extractions was investigated at 20oC by using Atomic Absorption and UV-visible Spectrophotometry. The influence of pH, ligand concentration, ionic strength, shaking time and ratio of aqueous-to-organic phases on extraction yield was tested at 20oC. The extractability of the tested metal ions were valuated.
In this research we have synthesized a new macrocyclic Schiff base (II) containing nitrogen- oxygen donor atoms which was designed and synthesized by reaction of: 1,4– bis (6',6'- methoxy -3- formyl phenyl)-1,4- dioxa butane (I). Identification of this macrocyclic schiff base: (II) 1,16- Diaza–[3,6;11,14-di (6',6'- methoxy phenyl)]-7,10,19,22 - tetraoxa cyclo tetra icozane-15,1dien was determined by (LC-MS) and spectroscopy (IR). The liquid- liquid extraction of metal such as Zn2+, Pb2+ and Ni2+ from aqueous phase to organic phase which doesn't in water. The effect of chloroform and dichloromethane as organic solvents over the metal extractions was investigated at 25± 0.10C by using atomic absorption Spectrometer and extraction percentage was calculated.
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