Spectral characterization and antibacterial activities of benzyloxybenzaldehydethiosemicarbazone*3,4- Dihydroxybenzaldehydeisonicotinoylhydrazone and their transitional metal complexes

Article abstract of DOI:10.1155/2011/579892

The synthesis and spectral characterization of benzyloxybenzaldehydethiosemicarbazone (BBTSC) and the study of antibacterial activity of ligands BBTSC, 3,4-dihydroxybenzaldehydeisoni-cotinoylhydrazone (3,4-DHBINH) and their transition metal complexes was

Full text of DOI:10.1155/2011/579892

ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
2011, 8(4), 1848-1858
http://www.e-journals.net
Spectral Characterization and Antibacterial Activities
of Benzyloxybenzaldehydethiosemicarbazone,
3,4- Dihydroxybenzaldehydeisonicotinoylhydrazone
and their Transitional Metal Complexes
LAKSHMI NARAYANA SUVARAPU§*, A VARADA REDDY#,
G. SATHEESH KUMAR and SUNG OK BAEK§
§School of Environmental Engineering, Yeungnam University
Gyeongsan-Si, Republic of Korea - 712 749
#Analytical Division, Department of Chemistry
S.V. University, Tirupati-517 501 India
Recombinant Gene Product (RGP),
International Centre for Genetic Engineering and Biotechnology (ICGEB),
New Delhi – 110067
lakshminarayana_chem@rediffmail.com
Received 12 March 2011; Accepted 14 April 2011
Abstract: The synthesis and spectral characterization of benzyloxy-
benzaldehydethiosemicarbazone (BBTSC) and the study of antibacterial activity of
ligands BBTSC, 3,4-dihydroxybenzaldehydeisoni-cotinoylhydrazone (3,4-DHBINH)
and their transition metal complexes was studied. The composition of the metal
complexes was also evaluated by using Job’s method, molar-ratio method and
Asmus’ method. The antibacterial activities of BBTSC, 3,4-DHBINH and their
complexes i.e., Cu(II)-BBTSC, Pd(II)-BBTSC, Cr(VI)- 3,4-DHBINH, Ti(IV)- 3,4-
DHBINH and Pd(II)-3,4-DHBINH were studied against two gram positive bacteria
and two gram negative bacteria. Antibacterial activities were evaluated by agar cup
well method with the help of Luria Bertoni plates.
Keywords: BBTSC, 3,4-DHBINH, Antibacterial activity,Transitional metal complexes
Introduction
Thiosemicarbazones form a class of mixed hard-soft oxygen/nitrogen-sulphur chelating ligands
that show a variety of coordination modes in metal complexes. The thiosemicarbazones can act
as a monodentate ligand that binds to the metal ion through the sulphur atom1 or as a
bidentate ligand that coordinates to the metal ion through the sulphur atom and one of the
nitrogen atoms of the hydrazine moiety to form four or a five membered chelate rings2,3.

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L. N. SUVARAPU et al.
The coordination capacity of thiosemicarbazones can be increased due to the presence of
aldehydes or ketones containing additional functional group(s) in position(s) suitable for
chelation4. Besides their interesting coordination chemistry, thiosemicarbazones have
attracted considerable interest because of their potentially beneficial biological activities
such as antiviral5, antitumour6, antimalarial7, antifungal8 and antibacterial9. The biological
activity of thiosemicarbazones and metal-thiosemicarbazones has been receiving
considerable attention recently10-12
.
A good number of reports are available on the biological activity of transition metal
complexes of thiosemicarbazones13-15. The mechanism of biological activity of thiosemi-
carbazones is due to their ability to inhibit the biosynthesis of DNA, possibly by blocking the
enzyme ribonucleotide diphosphate reductase; binding to the nitrogen bases of DNA, hindering or
blocking base replication; creation of lesions in DNA stands by oxidative rupture16. In some cases
the activity is associated with a metal atom. Several palladium(II) and platinum(II)
thiosemicarbazone complexes having potential antitumor activity have been recently reported17-20
Collins et al21 have reported the correlation between structure and antibacterial
activity in series of 2-acetylpyridinethiosemicarbazone. In many cases, by
.
a
coordination to different transition metal ions that can be found in biological systems, it
is possible to obtain complexes that are more efficient drugs than the corresponding free
ligands22-24. Some important thiosemicarbazones with antibacterial activity reported
earlier are discussed here under.
Kovala-Demertzi et al25 have reported the anti-tumor activity of 2-acetylpyridine-4N-
ethylthiosemicarbazone and its platinum(II) and palladium(II) complexes. Elena
Bermejo et al26 have reported the biological activities of complexes of zinc(II), cadmium(II),
mercury(II), palladium(II) and platinum(II) with 2-acetylpyridine- 4-methylthiosemi-carbazone
and its metal complexes assayed in vitro for antifungal activity against the pathogens
Aspergillus niger and Paecilomyces variotii. Among the above mentioned transition metal
complexes only zinc(II) complex shows some activity at a concentration of 600 µg mL-1.
The minimum inhibition zone for zinc(II) complex is found as 9.5 mm.
Dimitra Kovala-Demertzi et al27 have reported the antibacterial and antifungal activities
of nickel(II) and palladium(II) complexes of 2-acetyl-pyridinethiosemi-carbazone.
Antibacterial activities are evaluated against gram positive bacteria Staphylococcus aureus
and gram negative bacteria Escherichia coli. Antifungal activity is evaluated against candida
albicans.
Sulekh Chandre et al28 have reported the antimicrobial activities of copper(II) and
nickel(II) complexes with benzil bisthiosemicarbazone against the gram positive bacteria
(Bacillus macerans) and gram negative bacteria (Pseudomonas striata). The authors
reported that the metal chelates exhibit more inhibitory effects than the parent ligand.
Antibactrial activity of hydrazones and their complexes
Interest in the study of hydrazones has been growing because of their antimicrobial,
antituberculosis and antitumor activities29-30. Hydrazones play an important role in inorganic
chemistry, as they easily form stable complexes with most of the transition metal ions. The
development of the field of bioinorganic chemistry has increased the interest in hydrazone
complexes, since it has been recognized that many of these complexes may serve as models
for biological important species31. Coordination compounds derived from aroylhydrazones
have been reported to act as enzyme inhibitors and are useful due to their pharmacological
applications32-35
.

Spectral Characterization and Antibacterial Activities
1850
Hydrazones possessing an azometine –NHN=CH-proton constitute an important class of
compounds for new drug development. Therefore, many researchers have synthesized these
compounds as target structures and evaluated their biological activities.
Hydrazones and their metal complexes are biologically very active compounds. For
example Ragavendran et al36 have reported anticonvulsant activity of 4-aminobutyri-
cacidhydrazone, Abdel-Aal et al37 have reported antiviral activity of N-arylaminoacetyl-
hydrazones against Herper simplex virus-1 and Hepatitis-A virus(HAV), Walcourt et al38
have reported antimalarial activity of 2-hydroxy-1-naphthaldehyde -isonicotinoyl-
hydrazone and Savini et al39 have reported antitumor activity of 3- and 5-methylthio-
phene-2-carboxaldehyde α-(N)-heterocyclichydrazone derivatives. Recently critical reviews
have been published by various authors on antibacterial activity of hydrazones40-42
.
A thorough literary survey has revealed that a good number of thiosemicarbazone and
hydrazone complexes are evaluated for antibacterial activity against various bacteria. But
potentiality of these complexes is not fully utilized. Hence, the newly synthesized copper(II)
and palladium(II) complexes of benzyloxybenzaldehydethiosemicarbazone (BBTSC) and
vanadium(V), chromium(VI), titanium(IV) and palladium(II) complexes of 3,4-dihydroxy-
benzaldehydeisoni-cotinoylhydrazone(3,4-DHBINH) are tried to evaluate antibacterial
activity.
Experimental
Klebsiella pneumoniae, Staphylococcus aureus, Escherichia coli and Pseudomonas
o
aeruginosa were grown at 37 C and maintained on LB plates (Luria-Bertani broth, with
2.0% agar) for 18-20 h.
Assay of antibacterial activity by Agar cup well method
Preparation of overnight bacterial culture
The LB broth (Hi media) medium was inoculated with selected bacterial culture under sterile
conditions and incubated at 37 oC for 18-20 h. This developed inoculum was used for further assay.
Preparation of LB plates
The LB agar medium was prepared and poured in petri plates and allowed to solidification.
Inoculation of bacterial culture on LB medium by spread plate method
The overnight bacterial culture having 0.1; O.D (spectrophotometric value at 600 nm) of 0.1 mL
was spread inoculated on LB agar plate and left undisturbed for 3 min.
Preparation of agar cup wells and addition of metal solution
Using a sterile cork borer, wells were created on LB agar plate and the chelated metal stock
solution (Conc 2.0 mg mL-1) 30 micro L was added and kept for incubation at 37 oC for 20-24 h.
Synthesis of benzyloxybenzaldehydethiosemicarbazone (BBTSC)
Benzyloxybenzaldehydethiosemicarbazone was synthesized by refluxing a methanolic
solution containing 2.0 g of benzyloxybenzaldehyde (M.Wt. 212 g) and 1.0 g of
thiosemicarbazide (M.Wt. 91.13 g) for about 1 h 30 min. in a round bottom flask. The light
yellow colored product obtained was separated by filtration and dried. The product was
recrystalized from methanol. The purity of the reagent was checked by ascertaining the
melting point and elemental analysis.

1851
L. N. SUVARAPU et al.
Elemental analysis
The calculated data for C15H15 N3SO, (C, 63.15; H, 5.26; N, 14.73; S, 11.22%) is in good
agreement with the experimentally found data (C, 61.27; H, 5.37; N, 14.05; S, 9.90%) to the
above proposed molecular formula for BBTSC. The synthesis of BBTSC is presented in
Scheme 1.
S
O
-
H2N
H2O
S
O
N
H
NH2
+
N
O
N
H
NH2
Thiosemicarbazide
Benzyloxybenzaldehyde
Benzyloxybenzaldehydethiosemicarbazone
Scheme 1. Synthesis of BBTSC
Preparation of 3,4-dihydroxybenzaldehydeisonicotinoylhydrazone43
Equimolar quantities of 3,4-dihydroxybenzaldehyde (dissolved in alcohol) and
isonicotinichydrazide (dissolved in water) were taken in a 500 mL round bottom flask
and refluxed for 2-3 h. The contents were cooled and then filtered. The product (Scheme 2)
obtained was washed with aqueous methanol and finally recrystallized from rectified
spirit. The purity of the reagent was checked by TLC and melting point analysis
(m.p. 491-492 K).
N
HO
OH
H2N
HO
NH
-
H2O
+
N
O
NH
O
HO
Isonicotinichydrazide
3,4
-Dihy
droxy
benz
aldehy
O
N
de
3,4- Dihydroxybenzaldehydeisonicotinoylhydrazone
Scheme 2. Formation of 3, 4-DHBINH
Results and Discussion
Characterization of BBTSC
The synthesized reagent BBTSC was characterized by melting point determination,
1
elemental analysis, IR (Figure 1), H NMR (Figure 2), 13C NMR (Figure 3) and Mass
spectra (Figure 4).
Characterization of 3,4-DHBINH
It is evident from I.R. spectrum (Figure 5) that, C=N group is present in the compound
because the peak appears at 1600 cm-1. C=O(Stretching) amide peak appears at 1656.9 cm-1.
-OH group peak appears at 3484.6 cm-1, -NH peak appears at 3245 cm-1. From the above
data it is confirmed the formation of 3,4-dihydroxybenzaldehydeisonicotinoylhydrazone. A
0.1 mol L-1 stock solution was prepared by dissolving 2.57 g of 3,4–DHBINH in 40%
aqueous dimethyl formamide(DMF).
Antibacterial activity
In the present investigation, we studied the antibacterial activity of ligands BBTSC and
3,4-DHBINH and their complexes i.e., Cu(II)-BBTSC, Pd(II)-BBTSC, V(V)-3,4-DHBINH,

Spectral Characterization and Antibacterial Activities
1852
Cr(VI)-3,4-DHBINH, Ti(IV)-3,4-DHBINH and Pd(II)-3,4-DHBINH against two gram
positive bacteria (Klebsiella pneumoniae and Staphylococcus aureus)and two gram negative
bacteria (Escherichia coli and Pseudomonas aeruginosa). The results are reported Table 1
and Table 2.
Wavenumbers cm-1
Figure 1. Infrared spectrum of BBTSC
0
7
6
1
11
8
4
3
10
9
5
2
Figure 2. 1H NMR spectrum of BBTSC

1853
L. N. SUVARAPU et al.
Figure 3. 13C NMR spectrum of BBTSC
Figure 4. Mass spectrum of BBTSC
Figure 5. IR SPECTRUM of 3, 4-dihydroxybenzaldehydeisonicotinoylhydrazone

Spectral Characterization and Antibacterial Activities
1854
From the data in Tables 1 and 2, it is clear that the free ligands BBTSC and
3,4-DHBINH is inactive against the tested bacteria. BBTSC, on complexation with
Pd(II) and 3,4-DHBINH with Ti(IV) and Pd(II) there is a notable antibacterial activity.
From the results, it is conclusive that the Pd(II) complex with 3,4-DHBINH is effective
against S. aureus and E.coli than the Ti(IV) complex of 3,4-DHBINH. At the same time
the Ti(IV) complex of 3,4-DHBINH is effective against K. pneumoniae and
P. aeruginosa than the Pd(II) complex of 3,4-DHBINH. In case of Pd(II)-BBTSC
complex it is effective about S. aureus than the remaining tested bacterial stains. The
minimum inhibition concentration (MIC) of these complexes found to be 1000 µg mL-1.
From our observations, we conclude that the antibacterial activities are strongly
dependant on the central metal ions.
Table 1. Antibacterial activity of BBTSC and its complexes
Concentration,
µg mL-1
1000
Minimum inhibition zone, mma
S.No. Compound
K.pneumoniae S.aureus E.coli P.aeruginosa
-
-
-
-
-
-
-
1
2
3
BBTSC
-
-
2000
-
-
-
Cu(II)-
BBTSC
1000
-
-
-
-
2000
7.5
10.0
10.0
12.5
5.0
7.5
8.0
10.0
Pd(II)-
BBTSC
1000
2000
a
The results are average of two replicates
Table 2. Antibacterial activity of 3,4-DHBINH and its complexes
Concentration,
µg mL-1
1000
Minimum inhibition zone, mma
K.pneumoniae S.aureus E.coli P.aeruginosa
S.No.
1
Compound
3,4-DHBINH
-
-
-
-
-
-
-
-
-
-
-
2000
2
3
4
5
V(V)-3,4-
DHBINH
-
1000
-
-
-
-
2000
Cr(VI)-3,4-
DHBINH
-
-
-
-
1000
-
-
-
-
2000
Ti(IV)-3,4-
DHBINH
10.0
15.0
7.5
10.5
8.0
9.5
9.0
11.5
7.0
8.5
10.0
12.0
10.5
13.5
7.5
9.5
1000
2000
Pd(II)-3,4-
DHBINH
1000
2000
a
The results are average of two replicates
Absorption spectra of ligands and their metal complexes
Formation of complexes by ligands with the transition metal ions was also proved by the
absorption spectra of the complexes and ligands. It is further confirmed by composition
studies.
Absorption spectra of BBTSC and Pd(II)-BBTSC
The absorption spectrum of the Pd(II)-BBTSC complex was recorded against reagent as blank
and the absorption spectrum of BBTSC was recorded against solvent blank. The obtained

1855
L. N. SUVARAPU et al.
spectra have revealed that the Pd(II)-BBTSC complex and the reagent (BBTSC) have
maximum absorbances at 365 nm and 340 nm, respectively. The reagent has minimum
absorbance at the maximum absorbance of the complex and the reagent does not interfere
with the determination of palladium(II)44.
Absorption spectra of 3,4-DHBINH, Ti(IV)- 3,4-DHBINH and Pd(II)- 3,4-DHBINH
The absorption spectrum of Ti(IV)-3, 4-DHBINH complex was recorded against the reagent
blank. Similarly the absorption spectrum of the reagent (3,4-DHBINH) was recorded against
the solvent blank. From the absorption spectra it is cleared that the complex and reagent
have shown maximum absorptions at 370 nm and 340 nm, respectively. The reagent has
minimum absorbance at the maximum absorbance of the complex. The reagent absorbance
at the maximum absorbance of metal complex was further suppressed using suitable
concentration of reagent as blank and further absorbance measurements were made at
370 nm. The absorption spectra in the 300-600 nm range for 3,4-DHBINH and
Pd(II)-3,4-DHBINH complex45 were recorded. The formation of the 380 nm band in the
spectra must be connected with the chelate formation between Pd(II)- 3,4-DHBINH.
Composition of the metal complexes
Composition of Pd(II)-BBTSC complex
Job’s method of continuous variation, molar-ratio method and Asmus’ methods were
employed to elucidate the composition of the complexes.
Job’s method of continuous variation
Equimolar solutions (0.5×10-4 M) of palladium(II) and BBTSC were prepared. The metal
and reagent solutions were mixed in different proportions, keeping the total volume of the
mixture constant at 2.0 mL. In each case, 3.0 mL of sodium acetate-acetic acid buffer
(pH 5.0) was added to the mixture and the aqueous phase was shaken thoroughly with
10.0 mL of cyclohexanol. The organic phase was collected into a 25.0 mL standard flask and
made up to the mark with cyclohexanol. The absorbances of all the organic phases were
recorded at 365 nm against their reagent blanks. A plot was drawn between absorbance and
VM / VL+VM (where VL and VM are the volumes of the reagent and the metal, respectively).
From the graph, it was observed that one mole of palladium(II) reacts with one mole of
ligand and the composition of metal to ligand complex as 1:1.
Molar ratio method
In molar ratio method, different aliquots containing 1.0 mL of 0.5×10-4 M palladium(II), 3.0 mL
of sodium acetate-acetic acid buffer (pH 5.0) and varying concentrations (0.125×10-4-
2.5×10-4 M) of BBTSC were used to determine the metal to ligand ratio. The absorbances of the
extracted organic phases were recorded at 365 nm against their respective reagent blanks. A plot
was drawn between the absorbance and the concentration of the reagent. From the obtained
curve it was confirmed that one mole of palladium(II) complexes with one mole of BBTSC.
The composition of the metal to ligand was further confirmed by Asmus’ method also.
Composition of the Ti(IV)-3,4-DHBINH complex
Job’s method of continuous variation
Equimolar solutions (1.0×10−4 M) of titanium(IV) and 3,4-DHBINH were prepared. The metal and
reagent solutions were mixed in different proportions, keeping the total volume of metal and ligand
constant at 1.2 mL. In each case, 4.0 mL of sodium acetate-acetic acid buffer (pH 3.5) was

Spectral Characterization and Antibacterial Activities
1856
added to the mixture and the total volume of the solution was made up to 10.0 mL with
double distilled water. The absorbances of all the solutions were recorded at 370 nm against
their reagent blanks. A plot was drawn between absorbance and VM / VL+VM (where VL and
VM are the volumes of the reagent and the metal, respectively). From the graph, it was
observed that one mole of titanaium(IV) reacts with two moles of ligand shows the
composition of metal to ligand complex as 1:2.
Molar ratio method
In molar ratio method, different aliquots containing 1.0 mL of 1.0×10-4M titanium(IV),
4.0 mL of sodium acetate-acetic acid buffer (pH 3.5) and varying concentrations (0.25×10-4-
3.0×10-4 M) of 3,4-DHBINH were used to determine the metal to ligand ratio. The
absorbances of the solutions were recorded at 370 nm against their respective reagent
blanks. A plot was drawn between the absorbance and the concentration of the reagent.
From the obtained curve it was confirmed that one mole of titanium(IV) complexes with two
moles of 3,4-DHBINH.
Composition of the Pd(II)-3,4-DHBINH complex
Job’s method of continuous variation
Equimolar solutions (1.0×10−4 M) of palladium(II) and 3,4–DHBINH was prepared. The
metal and reagent solutions were mixed in different proportions, keeping the total volume of
metal and ligand constant at 1.0 mL. In each case, 4.0 mL of sodium acetate-acetic acid
buffer (pH 3.0) was added to the mixture and the total volume of the solution was made up
to 10.0 mL with double distilled water. The absorbance of all the solutions was recorded at
380 nm against their reagent blanks. A plot was drawn between absorbance and VM / VL+VM
(where VL and VM are the volumes of the reagent and the metal, respectively). From the
graph, it was observed that one mole of palladium(II) reacts with one mole of ligand shows
the composition of metal to ligand complex as 1:1.
Molar ratio method
In molar ratio method, different aliquots containing 1.0 mL of 1.0×10-4 M palladium(II),
4.0 mL of sodium acetate-acetic acid buffer (pH 3.0) and varying concentrations (0.25×10-4-
2.75×10-4 M) of 3,4-DHBINH were used to determine the metal to ligand ratio. The
absorbances of the solutions were recorded at 380 nm against their respective reagent
blanks. A plot was drawn between the absorbance and the concentration of the reagent.
From the obtained curve it was confirmed that one mole of palladium(II) complexes with
one mole of 3,4-DHBINH.
Conclusion
We confirmed the formation of BBTSC and 3,4-DHBINH with the help of various spectral
techniques. The composition of the metal complexes was also evaluated by various methods.
From the anti bacterial activity results, we concluded that the ligands BBTSC and
3,4-DHBINH were inactive against the tested bacteria strains. Out of six complexes the
three complexes i.e., Pd(II)-BBTSC, Ti(IV)-3,4-DHBINH and Pd(II)-3,4-DHBINH are
effective against the two gram positive bacteria (Klebsiella pneumoniae and Staphylococcus
aureus) and two gram negative bacteria (Escherichia coli and Pseudomonas aeruginosa).
The minimum inhibition zone of the complexes is increased with the increase in
concentration. From our results we conclude that the antibacterial activities of the
transitional metal complexes are strongly dependant of the central metal ions.

1857
L. N. SUVARAPU et al.
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