Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands

Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands

This thesis report four new chelating hydrazone ligands containing ONO- and ONN-donor atoms and their organotin(IV) complexes. Research works have been focused on the synthesis, spectroscopic characterization, structural elucidation and biological activities studies of these hydrazone ligands and t...

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Main Author: Irene, Foo Ping Ping
Format: Thesis
Language:English
Published: 2009
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://ir.unimas.my/id/eprint/30304/1/Irene.pdf
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id my-unimas-ir.30304
record_format uketd_dc
institution Universiti Malaysia Sarawak
collection UNIMAS Institutional Repository
language English
topic Q Science (General)
QD Chemistry
spellingShingle Q Science (General)
QD Chemistry
Irene, Foo Ping Ping
Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands
description This thesis report four new chelating hydrazone ligands containing ONO- and ONN-donor atoms and their organotin(IV) complexes. Research works have been focused on the synthesis, spectroscopic characterization, structural elucidation and biological activities studies of these hydrazone ligands and their organotin(IV) complexes. The four new chelating hydrazone ligands used were: pyruvic acid-4-hydroxybenzhydrazone [H3PAB] (1), methyl pyruvate-4-hydroxybenzhydrazone [H2MPB] (2), pyruvic acid-2- pyridylhydrazone [HPAP] (13) and benzoylacetone isonicotinylhydrazone [H2BAS] (20). New organotin(IV) complexes have also been derived from tly; se four mentioned hydrazone ligands with R,,, SfCl2_m [R = Me, nBu, tBu or Ph; m = I or 2] in the presence of base in absolute methanol using Schlenk vacuum line technique under dry N2-atmosphere. The analytical and physico-chemical techniques such as elemental analyses, UV-Visible, IR, and 'H NMR studies have been used for the characterization of hydrazone ligands (1-2, 13, 20) and their organotin(IV) complexes (3-12, 14-19, 21-26). Among them, molecular structures of [nBu2Sn(HPAB)] (4), [nBuSnC12(PAP)] (18) and [Me2Sn(BAS)] (21) have also been characterized by single crystal X-ray diffraction methods. Molar conductance values showed that all the organotin(IV) complexes (3-12, 14-19, 21-26) are non-electrolytes. New hydrazone ligands, [H3PAB] (1) and [H2MPB] (2) are reacted with organotin(IV) chloride(s) to torn [R2Sn(HPAB)] [R = Me (3), nBu (4), tBu (5) and Ph (6)], [RSnCI(HPAB)] [R = Me (7) and Ph (8)], [R2SnCI(HMPB)] [R = Me (9), nBu (10) and Ph (11)] and [MeSnC12(HMPB)] (12). The X-ray single crystal analysis data of [nBu2Sn(HPAB)] (4) confirmed that compound (4) is five-coordinated in a distorted trigonal-bipyramidal geometry configuration. [nBu2Sn(HPAB)] (4) is orthorhombic with space group C2/c. The ligand [H3PAB] (1) acts as a dinegative tridentate ligand coordinating via the carboxylic-O, imine-N and enolic-O atoms in the formation of [nBu2Sn(HPAB)] (4). From the elemental analyses and spectroscopic studies of ligand [H2MPB] (2) and its organotin(IV) complexes (9-12), [H2MPB] (2) is proposed to coordinate as a dinegative tridentate entity towards the central tin atom, coordinating through the carboxylate-O, the imine-N and enolic-O atoms to form organotin(IV) complexes (9-12). Another hydrazone ligand, [HPAP] (13) and its organotin(IV) complexes, [R2SnC1(PAP)] [R = Me (14), nBu (15) and Ph (16)] and [RSnC12(PAP)] [R = Me f 17), nBu (18) and Ph (19)] are also prepared and characterized. Single crystal X-ray data showed that [nBuSnCI2(PAP)] (18) has six coordination number in a distorted octahedral configuration. [HPAP] (13) acted as mononegative tridentate ligand which coordinated via carboxylic-O, imine-N and pyridyl-N atoms. The X-ray crystal structure proved that [nBuSnC12(PAP)] (18) is tetragonal with space group I4i/a. Reaction of [HZBAS] (20) with organotin(IV) chloride(s) produced [R2Sn(BAS)] [R = Me (21), nBu (22) and Ph (23)] and [RSnCI(BAS)] [R = Me (24), nBu (25) and Ph (26)]. X-ray crystallographic analysis revealed that [Me2Sn(BAS)] (21) is penta-coordinated and adopts a distorted trigonal-bipyramidal configuration via 0, N, 0-donor atoms from the [H2BAS] (20) which acted as dinegative tridentate ligand. The crystal structure of [Me2Sn(BAS)] (21) is monoclinic with space group P2(1)/n. he preliminary toxicity test revealed that all the organotin(IV) complexes (3-12, 14-19, 21-26) are more toxic against Artemia salina than the free hydrazone ligands [H2BAS] (1), [H2MPB] (2), [HPAP] (13) and [H2BAS] (20). In general, di-n-butyltin(IV) complexes (4, 10 and 15) were the most toxic with the lowest LC50 values for the hydrazone ligands [H3PAB] (1), [H2MPB] (2) and [HPAP] (13). The LC50 values for complex (4, 10 and 15) were 11.40, 26.07 and 13.24 μg/mL, respectively. However, in the series of ligand [H2BAS] (20), diphenyltin(IV) complex [Ph2Sn(BAS)] (23) was the most toxic with LC50 values of 15.31 μg/mL. The evaluation of antibacterial activities of ligand [H3PAB] (1) and its organotin(IV) complexes (3-8) showed that the complexes (3-8) are more active than the free hydrazone ligand [H3PAB] (1).
format Thesis
qualification_level Master's degree
author Irene, Foo Ping Ping
author_facet Irene, Foo Ping Ping
author_sort Irene, Foo Ping Ping
title Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands
title_short Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands
title_full Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands
title_fullStr Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands
title_full_unstemmed Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands
title_sort synthesis, characterization and biological activity of organotin (iv) complexes with hydrazine ligands
granting_institution Universiti Malaysia Sarawak (UNIMAS)
granting_department Faculty of Resource Science and Teknology
publishDate 2009
url http://ir.unimas.my/id/eprint/30304/1/Irene.pdf
_version_ 1783728381054943232
spelling my-unimas-ir.303042023-05-11T06:26:47Z Synthesis, characterization and Biological activity of organotin (IV) complexes with hydrazine ligands 2009 Irene, Foo Ping Ping Q Science (General) QD Chemistry This thesis report four new chelating hydrazone ligands containing ONO- and ONN-donor atoms and their organotin(IV) complexes. Research works have been focused on the synthesis, spectroscopic characterization, structural elucidation and biological activities studies of these hydrazone ligands and their organotin(IV) complexes. The four new chelating hydrazone ligands used were: pyruvic acid-4-hydroxybenzhydrazone [H3PAB] (1), methyl pyruvate-4-hydroxybenzhydrazone [H2MPB] (2), pyruvic acid-2- pyridylhydrazone [HPAP] (13) and benzoylacetone isonicotinylhydrazone [H2BAS] (20). New organotin(IV) complexes have also been derived from tly; se four mentioned hydrazone ligands with R,,, SfCl2_m [R = Me, nBu, tBu or Ph; m = I or 2] in the presence of base in absolute methanol using Schlenk vacuum line technique under dry N2-atmosphere. The analytical and physico-chemical techniques such as elemental analyses, UV-Visible, IR, and 'H NMR studies have been used for the characterization of hydrazone ligands (1-2, 13, 20) and their organotin(IV) complexes (3-12, 14-19, 21-26). Among them, molecular structures of [nBu2Sn(HPAB)] (4), [nBuSnC12(PAP)] (18) and [Me2Sn(BAS)] (21) have also been characterized by single crystal X-ray diffraction methods. Molar conductance values showed that all the organotin(IV) complexes (3-12, 14-19, 21-26) are non-electrolytes. New hydrazone ligands, [H3PAB] (1) and [H2MPB] (2) are reacted with organotin(IV) chloride(s) to torn [R2Sn(HPAB)] [R = Me (3), nBu (4), tBu (5) and Ph (6)], [RSnCI(HPAB)] [R = Me (7) and Ph (8)], [R2SnCI(HMPB)] [R = Me (9), nBu (10) and Ph (11)] and [MeSnC12(HMPB)] (12). The X-ray single crystal analysis data of [nBu2Sn(HPAB)] (4) confirmed that compound (4) is five-coordinated in a distorted trigonal-bipyramidal geometry configuration. [nBu2Sn(HPAB)] (4) is orthorhombic with space group C2/c. The ligand [H3PAB] (1) acts as a dinegative tridentate ligand coordinating via the carboxylic-O, imine-N and enolic-O atoms in the formation of [nBu2Sn(HPAB)] (4). From the elemental analyses and spectroscopic studies of ligand [H2MPB] (2) and its organotin(IV) complexes (9-12), [H2MPB] (2) is proposed to coordinate as a dinegative tridentate entity towards the central tin atom, coordinating through the carboxylate-O, the imine-N and enolic-O atoms to form organotin(IV) complexes (9-12). Another hydrazone ligand, [HPAP] (13) and its organotin(IV) complexes, [R2SnC1(PAP)] [R = Me (14), nBu (15) and Ph (16)] and [RSnC12(PAP)] [R = Me f 17), nBu (18) and Ph (19)] are also prepared and characterized. Single crystal X-ray data showed that [nBuSnCI2(PAP)] (18) has six coordination number in a distorted octahedral configuration. [HPAP] (13) acted as mononegative tridentate ligand which coordinated via carboxylic-O, imine-N and pyridyl-N atoms. The X-ray crystal structure proved that [nBuSnC12(PAP)] (18) is tetragonal with space group I4i/a. Reaction of [HZBAS] (20) with organotin(IV) chloride(s) produced [R2Sn(BAS)] [R = Me (21), nBu (22) and Ph (23)] and [RSnCI(BAS)] [R = Me (24), nBu (25) and Ph (26)]. X-ray crystallographic analysis revealed that [Me2Sn(BAS)] (21) is penta-coordinated and adopts a distorted trigonal-bipyramidal configuration via 0, N, 0-donor atoms from the [H2BAS] (20) which acted as dinegative tridentate ligand. The crystal structure of [Me2Sn(BAS)] (21) is monoclinic with space group P2(1)/n. he preliminary toxicity test revealed that all the organotin(IV) complexes (3-12, 14-19, 21-26) are more toxic against Artemia salina than the free hydrazone ligands [H2BAS] (1), [H2MPB] (2), [HPAP] (13) and [H2BAS] (20). In general, di-n-butyltin(IV) complexes (4, 10 and 15) were the most toxic with the lowest LC50 values for the hydrazone ligands [H3PAB] (1), [H2MPB] (2) and [HPAP] (13). The LC50 values for complex (4, 10 and 15) were 11.40, 26.07 and 13.24 μg/mL, respectively. However, in the series of ligand [H2BAS] (20), diphenyltin(IV) complex [Ph2Sn(BAS)] (23) was the most toxic with LC50 values of 15.31 μg/mL. The evaluation of antibacterial activities of ligand [H3PAB] (1) and its organotin(IV) complexes (3-8) showed that the complexes (3-8) are more active than the free hydrazone ligand [H3PAB] (1). Universiti Malaysia Sarawak (UNIMAS) 2009 Thesis http://ir.unimas.my/id/eprint/30304/ http://ir.unimas.my/id/eprint/30304/1/Irene.pdf text en validuser masters Universiti Malaysia Sarawak (UNIMAS) Faculty of Resource Science and Teknology

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