Journal of Materials Science Research and Reviews

6(1): 10-20, 2020; Article no.JMSRR.59725

Antimicrobial Activities of Co(II) and Sb(III)

Complexes of a Schiff Base Derived from
S-benzyldithiocarbazate (SBDTC) and
Cinnamaldehyde
Md. Kudrat-E-Zahan1, Md. Faruk Hossen1, Rausan Zamir1 and Md. Ali Asraf1*
1
Department of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh.

Authors’ contributions

This work was carried out in collaboration among all authors. Author MKEZ designed the study,
performed the statistical analysis, wrote the protocol and wrote the first draft of the manuscript.
Authors MFH and RZ managed the analyses of the study. Author MAA managed the literature
searches. All authors read and approved the final manuscript.

Article Information

Editor(s):
(1) Dr. Suraya Hani Bt Adnan, Universiti Tun Hussein Onn Malaysia, Malaysia.
Reviewers:
(1) Rajesh Kumar, India.
(2) Jairo Antonio Cubillos Lobo, Universidad Pedagógica y Tecnológica de Colombia, Colombia.
Complete Peer review History: http://www.sdiarticle4.com/review-history/59725

Received 25 May 2020

Original Research Article Accepted 03 August 2020
Published 08 August 2020

ABSTRACT

A bidentate Schiff base ligand having nitrogen sulphur donor atoms was derived from the
condensation of S-benzyldithiocarbazate (SBDTC) with cinnamaldehyde. The ligand was then
chelated with Co(II) and Sb(III). Molecular structures of the Schiff base ligand and its complexes
were established through elemental analysis, conductivity and magnetic susceptibility
measurements as well as spectroscopic data (FT-IR, UV-Vis and ESI-MS). The geometrical
structures are tetrahedral and octahedral for the cobalt complex and antimony complex
respectively. The biological activities of the ligand and its complexes were investigated against the
gram-positive and gram-negative bacteria and the fungus strain. The metal complexes were shown
to possess more.

Keywords: Schiff base; metal complex; antibacterial activity; antifungal activity.

_____________________________________________________________________________________________________

*Corresponding author: Email: asraf.chem@ru.ac.bd;

 Zahan et al.; JMSRR, 6(1): 10-20, 2020; Article no.JMSRR.59725
1. INTRODUCTION
Dithiocarbazic acid was first prepared by Curtius
in 1895 [1]. Later, a great number of S-alkyl/aryl-
esters, the Schiff bases of such compounds and
their corresponding metal complexes and
basically, NS-coordinated metal complexes have
been synthesized and examined for biological
applications such as antifungal, antibacterial,
antitumor, anticancer [2-8] antiamoebic [9,10]
and antiinhibitory cell migration activities [11] or
simply for the different coordination geometry
[12,13]. In addition, metal complexes derived
from dithiocarbazate esters and their Schiff
bases have also potential applications in the area
of electronic engineering as nano-materials [14],
non-linear optical materials (NLO) [15] and solar
cell components [16]. Very important classes of
mixed hard-soft nitrogen-sulfur donor ligands
may form from Dithiocarbazates [17]. These
types of ligands contain four potential donor
atoms of which two are sterically available at a
time to chelate metal ions. These ligands can
react with both transition and main group metals
due to the presence of hard nitrogen and soft
sulfur atoms [18] . Both NS (nitrogen-sulfur) and
SS (sulfur-sulfur) complexes are feasible in
principle. Free dithiocarbazaic acid and its S-
benzyl esters behave normally as NS donors
with formation of a five-membered chelate ring
[19], but SS coordination was also found making
a four-membered chelate ring [19].
Several reports on the antibacterial activities of
cobalt complexes have appeared in the literature,
wherein Co(II) complexes were the most studied,
apparently due to their aqueous stability,
availability and ease of synthesis [20]. Currently
many of antimony (III) complexes have been
clinically used because of their potential
biological activities and drug efficacies [21-26],
such as the treatment of a diversity of microbial
infections including leishmaniasis, parasitic
diseases, diarrhea, peptic ulcers, helicobacter
pylori, and so forth. Recently, the use of
antimony complexes in cancer chemotherapy
has become a topic of interest, and antimony(III)
compounds have been tested in vitro for their
cytotoxic effects on the proliferation of some
leukemia and solid tumor cells [27,28].
The major constituents of Cinnamomum cassia
(C. cassia) bark oils are cinnamaldehyde and
eugenol. Cinnamaldehyde is known as a
nontoxic food additive and extensively used as a
flavoring agent. It has also been established that
C. cassia bark-derived substances having
11
antimicrobial activities could be of real use as
new preventive agents [29,30]. Cinnamaldehyde
is an organic compound and very crucial to
inhibit the growth of bacterial species. Some of
the cinnamomum species have been tested in
terms of their chemical composition, applications
as antibacterial, anticancer and also in food
technology applications [29].
The present work represents the coordination
behavior of the Schiff base derived from S-
benzyldithiocarbazate (SBDTC) and
cinnamaldehyde with Co (II) and Sb(III) and
study of their antimicrobial activities.
2. MATERIALS AND METHODS
2.1 Reagents
CoCl2.6H2O, Sb(NO3)3, KOH, CS2, hydrazine
hydrate, cinnamaldehyde, benzyl chloride, DMF,
DMSO, CH3OH, and C2H5OH used in this works
were purchased from Sigma‐Aldrich and Merck
and used as received.
2.2 Instrumentation
Microanalysis (C, H, and N) for the ligand and
complexes were carried out on a Perkin‐Elmer
automatic equipment model 240B. The melting
points of synthesized compounds were obtained
on a digital melting point apparatus (METTLER
TOLEDO). Conductivity measurements were
-3 -
measured of freshly prepared 1.0×10 mol x dm
3
DMSO solutions of the synthesized compounds
using a Jenway 4071 digital conductivity meter at
room temperature. FT-IR spectra of the ligand
and its complexes were recorded using KBr disc
method on a Nicolet 170 SX FT-IR spectrometer.
UV-vis spectra were measured for 10−3 M
solutions in DMSO at 25°C using a Shimadzu
160 spectrophotometer. ESI-MS spectra were
recorded with an Agilent Technologies MSD SL
Trap mass spectrometer with ESI source coupled
with an 1100 Series HPLC system for the
confirmation of molecular formulas of
compounds. Magnetic moments were measured
using a magnetic susceptibility balance (Johnson
Matthey Catalytic System Division).
2.3 Preparation of S-benzyldithiocar-
bazate (SBDTC)
SBDTC was prepared following the reported
procedure [31]. Potassium hydroxide (0.05 mol)
was dissolved in ethanol 90% (50 mL). To this
solution, hydrazine hydrate (0.05 mol) was added
 Zahan et al.; JMSRR, 6(1): 10-20, 2020; Article no.JMSRR.59725
and the mixture was cooled in an ice-salt bath to
0°C. Carbon disulfide (0.05 mol) was added drop
wise with constant stirring over a period of one
hour. During this time, two layers were formed.
The light-brown lower layer was separated and
dissolved in 40% ethanol (50 mL), maintained at
5°C. The mixture was kept in ice-bath and to this
benzyl chloride (0.05 mol) was added drop wise
with vigorous stirring. The white product
(SBDTC) formed was filtered and washed with
ethanol. It was recrystallized from absolute
ethanol after drying. The recrystallized SBDTC
was dried and kept in a desiccator.
2.4 Preparation of the Cinnamaldehyde
Schiff Base of SBDTC, Benzyl 2-(3-
phenylallylidene) Hydrazinecarbodi-
thioate
Ethanolic solution (50 mL) of SBDTC (10 mmol)
was mixed with equimolar ethanolic solution (20
mL) of cinnamaldehyde. The mixture was
refluxed for 40 mins. The yellow precipitate which
formed was separated and dried in vacuo over
anhydrous CaCl2.
2.5 General Method for the Preparation of
Complexes with the Schiff Base,
Benzyl 2-(3-phenylallylidene)
Hydrazinecarbodithioate
Metal salt (0.5 mmol) was dissolved in absolute
ethanol (20 mL) and to this, Schiff base ligand (1
mmol) dissolved in hot absolute ethanol (70 mL)
was added. The mixture was then refluxed for 30
mins and then cooled. The precipitate formed
was filtered off and washed with ethanol and
dried in vacuo over anhydrous CaCl2.
The synthetic pathway of the metal complexes is
shown in equation (i) – (ii).
Scheme 1. Preparation of SBDTC
12
(i) CoCl2 .6H2O + NS → [Co(II)(NS)2]
(ii) Sb(NO3)3 + NS →
[Sb(III)(NS)2(NO3)(H2O)]
NS = Cinnamaldehyde Schiff base of
SBDTC, benzyl 2-(3-phenylallylidene)
hydrazinecarbodithioate
2.6 Metal Content Estimation
A known quantity of metal complex was put into
a conical flask whose weight was known. Then,
concentrated H2SO4 (500 L) was added. It was
fumed until dry and the process was repeated
three times. Concentrated HNO3 (500 L) and
HClO4 (500 L) were then added and the mixture
was further fumed until dry. The process of
adding acids and fuming to dry was continued
until there was no black materials. 100 mL
distilled water was added to dissolve the residue.
Finally, the weight of the metal was estimated
complexometrically and gravimetrically using
EDTA (Ethylenediamine tetraacetic acid) and
DMG (Dimethyl glyoxime) [32].
2.7 Antimicrobial Activity
Disc-agar diffusion method was used to check
the antimicrobial activity of the Schiff base ligand
and its metal complexes in DMF against two
Gram positive bacteria, Staphylococcus aureus
and Bacillus subtilis, two Gram negative bacteria,
Salmonella typhimurium and Escherichia coli and
two fungus strains Candida albicans and
Aspergillus fumigates. The antibiotic
chloramphenicol was used as reference in the
case of Gram-positive bacteria, cephalothin in
the case of Gram-negative bacteria and
cycloheximide in the case of fungi.
 Zahan et al.; JMSRR, 6(1): 10-20, 2020; Article no.JMSRR.59725
Scheme 2. Synthesis cinnamaldehyde Schiff base of SBDTC
3. RESULTS AND DISCUSSION
3.1 Synthesis
The Schiff base ligand was synthesized by 1:1
condensation of S-benzyldithiocarbazate
(SBDTC) and cinnamaldehyde in ethanol under
reflux, which on following reaction with metal
salts in 2:1 molar ratio, generated the metal
complexes. All the synthesized compounds are
air stable and non-hygroscopic.
3.2 Elemental Analysis
The microanalysis data (Table 2) indicates that
the complexes are mononuclear. These data
also exposed that the metal-to-ligand ratio for the
synthesized complexes were 1:2. The proposed
structure of the ligand and complexes were
consistent with elemental analysis data.
3.3 Molar Conductivity Measurements
The molar conductivity of the synthesized
compounds was determined at room temperature
at a concentration of 10-3 M in DMSO. The
conductance value exposed that the complexes
are non-electrolyte in nature (Table 1) [33].
3.4 FI-IR Data Analysis
Condensation of SBDTC with cinnamaldehyde
provided the isomeric Schiff base (Scheme 2)
with high yield in a neutral medium. The Schiff
base exists in tautomeric forms through the loss
of thiol protons as shown in Fig. 1. Schiff base
behaved as uninegatively charged bidented
ligand by coordinating through the thiol sulfur and
the azomethine nitrogen. The IR spectra of the
13
-1
Schiff base showed strong band at 3106 cm
due to the vibration of secondary amine group
[v(N-H)] of the free ligand. The thione form is
relatively unstable in the monomeric form and
tend to turn to the more stable thiol form by
enethiolization in solution (Fig. 1). The absence
of v(S-H) absorbance at approximately 2575 cm-1
indicated that in the solid state, the Schiff base
exists primarily in the thione form. The
disappearance of v(N-H) band in the FT-IR
spectra of the metal complexes suggested
deprotonation and consequent coordination
through the thiolate anions. The Schiff base also
showed strong band at 1623 cm-1 assigned to
the v(C=N) stretching. In the metal complexes,
this band shifted to lower frequencies due to the
lowering of the C=N bond order as a result of the
metal–nitrogen bond formation. The Schiff base
also displayed v(C=S) stretching at 1031 cm-1.
The v(C=S) mode observed in the free ligand
disappeared in the complexes, thus supporting
the above argument of thiolate bonding with
metal ions. Consequently, the v(C-S) mode was
observed in the spectra of the complexes
supporting thiolate coordination.
The Schiff base coordinated to the metal through
the thiolate sulphur and the azomethine nitrogen
atoms as evident from the FT-IR spectrum of the
-1
complexes showing bands at 384 and 385 cm
due to M-S bond stretching and bands at 461
-1
and 485 cm due to M-N bond stretching.
In the Sb(III) complex, the nitrate ion is O-
coordinated in monodentate fashion [34,35].The
three IR-active stretching modes expected for
nitrate group coordinated metal complex and
would be a low-frequency ν(O−N) band for the
coordinated oxygen and two (symmetric and
 Zahan et al.; JMSRR, 6(1): 10-20, 2020; Article no.JMSRR.59725

Table 1. Analytical data and physical properties of the compounds

Compounds Color Melting point or Molar conductance

-1 2 -1
decomposition temperature (Ω cm mol )
( 5°C)
NS White 181 2.50
[Co(II)(NS)2] Reddish black 208 3.15
[Sb(III)(NS)2(NO3)(H2O)] Yellow 207 2.90

Table 2. Microanalysis data of the ligand and its complexes

Compound Found (Calculated) (%)

Metal C H N
NS - 65.21 (65.35) 5.09 (5.16) 8.88 (8.97)
[Co(II)(NS)2] 8.58 (8.64) 59.73 (59.89) 4.37 (4.43) 8.13 (8.22)
[Sb(III)(NS)2(NO3)(H2O)] 14.57 (14.76) 49.28 (49.52) 3.68 (3.91) 8.33 (8.49)

Fig. 1. Tautomeric forms (a) Thione form (b) Thiol form

-1
Table 3. Important infrared spectral bands of the ligand and the metal complexes (cm )

Compound (N-H) (C=S) (C=N) (C-S) (M-S) (M-N) (NO3)

NS 3106 1031 1623 - - - -
[Co(II)(NS)2] - - 1603 748 384 461 -
Sb(III)(NS)2(NO3)(H2O)] - - 1540 763 385 485 1475, 1384, 1157

asymmetric) modes for the uncoordinated NO2
fragment. Three bands at 1475, 1384, and 1157
cm−1 were found in the IR spectrum of the
antimony complex [34]. The broad band
appeared at 3436 cm-1 together with new band at
-1
685 cm in the spectra of the Sb(III)l complex
confirmed the presence of coordinated water
molecules [36].
3.5 Magnetic Moment and Electronic
Spectra
In order to obtain further structural information on
the metal complexes, the magnetic moments and
electronic spectra were measured and the results
tabulated in Table 4. The electronic spectra of
the ligand, L and all the complexes were
recorded in DMSO at ambient temperature (Fig.
5). UV-visible spectral data are given in Table 3.
The absorption band at 272 nm of the Schiff
base ligand is due to benzene → ∗ transition
[37]. Another band at 334 nm is attributed to the
→ ∗ transition of the non-bonding electron
located on azomethine nitrogen atom of the
ligand.
For the tetrahedral Co(II) complex two bands are
appeared at 480 and 378 nm corresponding to
4 4 4 4
A2(F) → T2 (F) and A2 (F) → T1(F) transitions,
respectively, in addition to a charge transfer at
266 nm. The magnetic moment of tetrahedral,
Co(II) complex lies in the range 4.2 to 4.7 B.M.
while for octahedral Co(II) complexes it falls
between 4.4 to 5.5 B.M. The observed value
in the present case is 4.36 B.M. The
electronic spectra and magnetic moment value
suggest a tetrahedral environment around Co(II)
ion.
In the UV-visible spectrum of the Sb (III)
complex, absorption peaks are observed around
4 4
264, 310, 426 nm regions due to T1g (F) → T1g
4 4 4 4
(P), T1g (F) → A2g (P), and T1g (F) → T2g (F),
transitions respectively. The electronic spectral
peak positions and diamagnetic nature indicates
an octahedral configuration for the complex.

14
 Zahan et al.; JMSRR, 6(1): 10-20, 2020;; Article no.JMSRR.59725
no.

Fig. 2. FTIR spectrum of cinnamaldehyde schiff base of SBDTC (NS)

Fig. 3. FTIR spectrum of the complex of [Co(II)(NS)2]

Table 4. Electronic spectral data of the compounds

Compound eff (BM) Band Position (λ nm) Assignments

*
NS - 334 n →π
272 π → π*
4
[Co(II)(NS)2] 4.36 480 A2(F) →4T2 (F)
4 4
378 A2 (F) → T1(F)
266 CT
4 4
Sb(III)(NS)2(NO3)(H2O)] Dia 426 T1g (F) → T2g (F)
4
310 T1g (F) → 4A2g (P)
4 4
264 T1g (F) → T1g (P)

15
 Zahan et al.; JMSRR, 6(1): 10-20, 2020;; Article no.JMSRR.59725
no.

Fig. 4. FTIR spectrum of Sb(II)(NS)2(NO3)(H2O)]

Fig. 5. UV-visible
visible spectrum of the synthesized compounds

Fig. 6. ESI-MS
MS spectra of (a) ligand (NS); (b) [Co(II)(NS)2] and(c) Sb(II)(NS)2(NO3)(H2O)]

16
 Zahan et al.; JMSRR, 6(1): 10-20, 2020; Article no.JMSRR.59725

3.6 ESI-MS Spectral Studies
Es-ms has been increasingly used as a dominant
structural characterization method in coordination
chemistry. The spectra of the ligand and co(ii)
and sb(iii) complexes show molecular ion peaks
at m/z = 312.45, 681.20 and 824.62 amu
respectively. The m/z values, 312.45, 681.20 and
824.62 are equivalent to the molecular mass of
the ligand, co(ii) and sb(iii) complex respectively.
The molecular ion peaks are in good agreement
with the proposed molecular formulae indicated
from microanalysis.
3.7 Structures
On the basis of the different physicochemical and
spectral data presented and conferred above, the
structures of the Co(II) and Sb(III) complexes are
shown in Figs. 7 and 8.

SCH2C6H5

SCH2C6H5

Fig. 7. Tetrahedral structure of the Co(II) complex

Fig. 8. Octahedral structure of the Sb(III) complex

Table 5. Biological activity of the ligand and complexes expressed in mean of inhibition zone
diameter (mm)

Compound Gram-positive Gram-negative Bacteria Fungi

Bacteria
Staphyl- Bacillus Salmonella Salmonella Candida Candida
ococcus subtilis typhimurium typhimurium albicans albicans
aureus
NS 6 5 2 4 4 5
[Co(II)(NS)2] 23 25 20 19 15 21
Sb(II)(NS)2(NO3)(H2O)] 20 22 23 21 17 24
Reference 34 36 27 24 31 29

17
 Zahan et al.; JMSRR, 6(1): 10-20, 2020; Article no.JMSRR.59725

3.8 Antimicrobial Studies science, rajshahi university, bangladesh. The

authors are also thankful to department of
The biological activity of the Schiff base ligand chemistry, rajshahi university, bangladesh for
and its metal complexes were investigated providing laboratory facilities to conduct this
against the sensitive organisms Staphylococcus works.
aureus and Bacillus subtilis as Gram-positive
bacteria, Salmonella typhimurium and COMPETING INTERESTS
Escherichia coli as Gram-negative bacteria,
Candida albicans and Aspergillus fumigatus as Authors have declared that no competing
fungus strains. It was observed that the biological interests exist.
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