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Data Jurnal
Data Jurnal
Data Jurnal
Green approach to synthesize, - Penggerusan FTIR: Absorption band for 1,10- - UV-Vis: The ternary schiff base Distorted square pyramidal
spectral investigation and biological - The amino acids (tyrosine, phenanthroline saw at 1514 cm-1 copper(II) complexes showed geometry
applications of potentially active isoleucine), KOH and 2,4- and for thiourea at 3145 cm-1. absorption bands within the vary
ternary schiff base copper(II) dihydroxy benzaldehyde of Further the bands observed around 226–254 nm relates to p-p* shift of
complexes (Dinesh Karthik et al., equimolar quantity (4 mmol) were 540– 514 cm-1 can be ascribed to t phenyl group. The assimilation
2020) taken in a mortar and grinded for (Cu–N) linkage in addition to band saw within the vary of 360–
ten minutes with a pestle at room around 487–443 cm-1 v(Cu–O) 407 nm are due to n-p* shift due to
temperature. The white or light- linkage respectively. –CH = N- group. UV–Visible spec-
weight yellow colour paste is tra of all Cu(II) complexes showed
created that change to a strong UV-Vis: The ternary schiff base weak intensity combination band
powder on nonstop granulating copper(II) complexes showed next to 602, 608, 611 and 624 nm
for 20–30 min. absorption bands within the vary are owing to d-d shift.
- 226–254 nm relates to π → π* shift
of phenyl group. The assimilation - FTIR: Infra-red spectra of copper(II)
band saw within the vary of 360– complex obtained from template
407 nm are due to n- π * shift due to method showed a strong
–CH = N- group [16]. UV–Visible absorption band at 1616–1597 cm-
spectra of all Cu(II) complexes 1 individually attributable to the
showed weak intensity combination corresponding azomethine
band next to 602, 608, 611 and 624 nitrogen bonding eith copper metal
nm are owing to d-d shift. From atom. A wide band in the area
the electronic spectrum info, all 3483– 3203 cm-1 is because of
Cu(II) complexes have distorted phenolic OH group . An absorption
square pyramidal geometry. band saw in 1328–1377 cm-1 range
is transferable to the symmetric
stretch of –COOH cluster.
Asymmetric stretch (vasCOO-) was
seen in the range of 1539–1587
cm-1. Difference in asymmetric and
symmetric stretching frequencies
[Dt =(vasCOO- - vsCOO-)] were seen
as high when compare to free
COO– (177 cm-1). Likewise the
phenolic C-O vibrations are 1246–
1220 cm?1 recommend the
coordination of ligand with copper.
Carboxylic acid proton andhy-
droxyl proton is deprotonated by a
strong base KOH. Of the two – OH
groups present in the 2,4-dihydroxy
benzaldehyde, the –OH group
which is ortho to aldehyde is more
acidic. Hence it is easily
deprotonated and the oxygen
involves in the coordination of the
Cu–O linkage. Absorption band for
1,10-phenanthroline saw at 1514
cm-1 and for thiourea at 3145
cm?1. Further the bands observed
around 540 – 514 cm?1 can be
ascribed to t (Cu–N) linkage in
addition to around 487–443 cm-1 t
(Cu–O) linkage respectively 3.5.
Synthesis, Spectral Characterisation LIGAN 1 LIGAN 1 LIGAN 1: 2-methoxy-6-((p-
and MIC Evaluation of Schiff Base - O-vanillin (0.002 mol, 2.1342 g) - Bentuk: solid/serbuk tolylimino)methyl) phenol
Ligands Derived from o-Vanillin and p-toluidine (0.002 mol, 3.0430 - Warna: oranye LIGAN 2: 2-((2-hydroxy-3-
(Govindaraj & Rasikamary, 2018) g) dissolved separately in ethanol - % Yield: 80% methoxybenzylidene) amino)benzoic
and were mixed in RB flask - MPA: 91oC acid
- Direfluks selama 3 jam lebih di - FTIR: 1585 cm-1 corresponds to ν LIGAN 3: 3-methoxy-4-((3-
atas waterbath (>C=N-) hydroxyphenylimino) methyl) phenol
- Didinginkan hingga senyawa - UV-vis: two absorption maxima at
berwarna oranye terpisah lalu 321.22 nm (35587 cm-1) and
difiltrasi 281.25 (31153 cm-1) which may be
- Dicuci dengan sedikit alkohol dan assigned to π-π* and n-σ*
akuades lalu dikeringkan transition respectively.
- HNMR: δ 8.9 ppm suggesting the
LIGAN 2 presence of –CH=N-
- O-vanillin (0.01 mole, 1.52 g) and
2-aminobenzoic acid (0.01 moles, LIGAN 2
1.367 g) were dissolved separately - Bentuk: solid/serbuk
in ethanol. - Warna: Brick merah
- The o-vanillin solution was added - % Yield: 79%
drop wise. - MPA: 99Oc
- Lalu distirrer selama 1 jam. - FTIR: 1602 cm-1 is assigned to the
- Pelarut diuapkan lalu didingankan overlap of ν (C=O) and ν (>C=N-)
pada suhu ruang hingga senyawa stretching frequencies.
berwarna merah terpisah.
- Dicuci dengan sedikit metanol lalu - UV-Vis: three bands at 276 nm
dikeringkan. (36232 cm-1) suggesting the
presence of π-π* transition, 315
LIGAN 3 nm (31746 cm-1) and 356 nm
- O-vanillin (0.002 mole) and 3- (28090 cm-1).
aminophenol (0.002 mole) - HNMR: at δ 8.85 ppm is assigned to
dissolved separately in ethanol are (-CH=N-)
mixed in RB flask and heated.
- Di refluks selama 4 jam di atas
waterbath. LIGAN 3
- Campuran didinginkan hingga - Bentuk: solid/serbuk
senyawa berwarna terpisahkan. - Warna: dark oranye
- Difiltrasi lalu dibilas dengan sedikit - % Yield: 84%
metanol dan dikeringkan. - MPA: 140Oc
- Progress diamati dengan TLC - FTIR: 1603 cm-1 corresponds to ν
- (>C=N-) and ν (>C=O) (phenolic)
displayed at 1460 cm-1. The broad
band ranges from 3403- 3474 cm-1
which is the characteristic
frequency of hydrogen bonded ν
(O-H).
- UV-Vis: at 210.38 nm, 228.48 nm,
310.22 nm at the frequency of
47431 cm-1, 43767 cm-1 and
32235 cm-1 could be assigned to π-
π* and n-σ* transitions are due
aromatic part of ligands of
azomethine linkage in the Schiff
Bases.
- HNMR: at δ8.8 ppm a single peak
CH=N- linkage.
Synthesis, XRD and spectroscopic - Reflux [Cu(L)]: Yield: 69%. Anal. Calc. (%) for The IR Spectra of ligand and its Square planar
characterization of - The ethanol solvent is cheap, (C26H22CuN6O5) (562 g mol1): C, metal complexes were obtained
pharmacologically active Cu(II) and available, and less toxic than other 55.56; H 3.95; N, 14.95. Found: C, on a Perkin-Elmer Series 2000
Zn(II) complexes (Gull & Hashmi, solvents. Ethanol dissolves the 54.10; H 3.88; N, 13.90. FT-IR (KBr), apparatus in the range
2017) ligand at boiling temperature and cm1: ʋ(NeH) 3342, ʋ(C]N) 1610, 4000-200 cm-1. The infrared spectra
due to its miscibility with water, it ʋ(C]O) 1710, v(NO) 1610, ʋ(MeN) of the synthesised primary
is suitable for the synthesis of the 446. 1H NMR (d-CDCl3): 9.0 (s, NH); Schiff base ligand (Fig. S1) shows the
complex. To the solution of N–N′ 3.92 (s, eNH2); 7.10e8.0 (m, Ar-H) absorption band at 1625 cm1
-(1,2-diphenylethane-1,2- ppm. UV/Vis (DMSO, lmax (nm): 642, corresponds to the imine (>C=N)
diylidene)bis(3- 508. MS (m/z): 561 [M]+. group [21] and a strong band at
Nitrobenzohydrazide) (1 mmol, 1710 cm1 corresponding to the
540 mg) in ethanol (100 mL), >C=O group which confirms the
CuSO4·5H2O (1 mmol, 250 mg) complete condensation of the two
dissolved in distilled water (10 mL) reacting moieties. In addition to
was added. The above reaction these peaks an absorption bands
mixture was stirred and heated observed in the region of
under reflux for six hours. After
completion of the reaction, the 3340-3330 cm-1 and 1500-1630 cm-1
formed precipitate was fltered of are assigned to the –NH group and –
and rinsed with ethanol and dried, NO group present in the ligand.
and after that, recrystallized using While as in case of metal complexes
ethanol. (Fig. S2) the strong band at 1625
cm1 is shifted to lower frequency
numbers by 15-5 cm-1 leading to the
confirmation of coordination
through the imino (>C=N) group to
the metal atom in complexes. Also
there is an occurrence of new bands
in the region 460-420 cm-1 which has
been attributed to M-N bonds
respectively [22]. The IR spectral
bands of metal complexes are
summarized in Table 2.
- Refluks - The final solid was dried in oven at
- 80◦C for 3 h (yield = 3.8 g, 86.95%).
Synthesis, characterization, Refluks - C28H24CuN6O12S
and nonlinear optical properties To the solution of N–N′-(1,2- - Colour: dark green
of copper (II) ligand Schif diphenylethane-1,2-diylidene)bis(3- - Yield: 0.61 g, 83%
base complexes derived Nitrobenzohydrazide) (1 mmol, 540 - m.p.: 184–186 °C
from 3‐Nitrobenzohydrazide mg) in ethanol (100 mL), - IR (KBr, cm−1): 3205, 3079, 3057,
and benzyl (Tahmasbi et al., 2023) CuSO4·5H2O (1 mmol, 250 mg) 1682, 1525, 1348, 1263, 1150,
dissolved in distilled water (10 mL) 1067, 754, 716, 689
was added. Te above reaction
mixture was stirred and heated
under refux for six hours.
Synthesis, Spectroscopic Synthesis of Metal(II) Complexes. To - FTIR metal kompleks: C=N (1606), The absorption at 14265 cm−1 with - Square planar [Cu(CDTMP)2] (L15)
Characterization, and Biological a solution of (0.70 g, 2 mmol) 4-((4 C-O (1300), N=N (1482), M-N (584), high molar intensity (1100 L mol−1 [Cu(4-((4-klorofenil)dianzenil)-2-
Activities ofMetal Complexes of 4- chlorophenyl)diazenyl)-2- M-O (590) cm −1) of copper(II) complex (𝐋𝟏𝟓) is ((p-tolilimino)metil)fenol)]
((4-Chlorophenyl)diazenyl)-2-((p- ((ptolylimino)methyl)phenol - Mp complex: 298-300 tentatively assigned to 2B1g → 2A1g
tolylimino)methyl)phenol (Anitha et (CDTMP) in 20 mL ethanol was - m/z ion: 759 transition suggesting square planar
al., 2013) added 1 mmol of metal salt geometry. An additional band
(CuCl2⋅2H2O). The solution was appears at 22573 and 25706 cm−1
stirred for 1 h at room temperature, which may be due to intraligand
and the coloured complexes charge transfer (INCT) in the UV
precipitated upon concentration was region, and the molar extinction
filtered, washed with ethanol, and coefficient (1800, 1845 L mol−1 cm −1)
dried under vacuum. The of charge transfer transitions is
oxovanadium complex was higher than the d-d transition. The
synthesized from the ligand and magnetic moment value 2.01 B.M.
oxovanadium sulfate by adopting falls within the range normally
the above method under reflux for 3 observed for square planar Cu(II)
h and concentrating the solution complexes
through rotoevaporation. The yield
obtained was 60–70%.
Investigation of molecular structure Refluks - % Yield BS: 80%
and solvent/temperature effect on Sintesis BS: The title compound was - MP BS: 164-166
tautomerism in (E)-4,6-dibromo-3- synthesized with condensation - FTIR
methoxy-2-[(p-tolylimino)methyl] reaction of 3,5-dibrom-2-hydroxy-6- - UV-Vis
phenol, a new thermochromic Schiff methoxybenzeldehyde (0.2 g, 0.65 - XRD
base, by using XRD, FT-IR, UV–vis, mmol) and p-toluidine (0.07 g, 0.65 - NMR
NMR and DFT methods (Kaştaş et al., mmol). The resulting solid after - DFT
2019) reflux for 1 h was filtered, washed
and dried. The suitable crystals of
the com
Schiff bases and schiff base metal Ramasamy et al (2010) studied the
complexes: from syntheses to antimicrobial activities of complexes
applications (Elom, 2016) of tridentate Schiff base ligands
containing pyrazolone moiety
and observed that metal complexes
of Vo(II), Cu(II), Fe(III) and Co(II) with
the ligand showed enhanced
antibacterial activity against
staphylococcus aureus, Escherichia
Coli, and antifungal activity against
C. albicans, Rhizopus Sp, Aspergillus
niger. Metal complexes of 2 –
thiophenicarboxaldehyde and 2-
aminobenzoic acid have been noted
(Roy et al.,2007) to posses antitumor
activities. Also Schiff bases derived
from gossypol and silver complexes
of Schiff bases have been noted to
show high antiviral activity (Anant
and Devjani,2011). It has been noted
that fluorination on aldehyde part of
Schiff bases enhances insect
acracicidal activity and Schiff bases
derived from sulphur thiadizole and
salicylaldehyde and their complexes
exhibit high toxicity against insects
(Anant and Devjani,2011).
Spectral, magnetic and thermal Among these species, a special Tetradentate ligand (H2L) having a [Cu2LCl2] : π → π*
characterization of new Ni(II), attention has been paid to the divergent ONNO donor atom set was
Cu(II), Zn(II) and Cd(II) complexes chemistry of Schiff bases containing synthesized by [1 + 2] condensation
with a bischelate Schiff base (Olar et supplementary donor atoms beside of 3,3’-dimethylbenzidine with o-
al., 2017) azomethine nitrogen in suitable vanillin in ethanol as reported.
positions in the molecule that allow Nickel(II), copper(II), zinc(II), and
a stabile chelate ring formation. cadmium(II) complexes with Schiff
Complexes with such ligand usually base were obtained from refluxing
can be obtained either by direct an ethanol solution of ligand and
synthesis or by template hydrated metal(II) (M: Ni, Cu, Zn, Cd)
condensation. chloride in a 1:2 molar ratio, in the
pres-
Some species derived from ence of triethylamine.
functionalised aromatic car-
bonyl [9–30] and/or aromatic For the anhydrous species the
amines derivatives behave as beginning temperature of
effective and stereospecific catalysts the thermal decomposition
for a variety of reactions that involve increases in order Cu(II)<Ni(II)
both inorganic and organic <Zn(II)<Cd(II). This behavior could be
compounds. Moreover, some correlated with the ionic radius
complexes display antimicrobial, increasing which leads to relaxation
cytotoxic, SOD-like behavior or of the steric impediments in a
antiviral activity. The activity was tetrahedral stereochemistry.
correlated with the ligand and
metallic ions specificity. The
complexes exhibit an enhanced
activity in comparison with the free
ligand. Thermal behavior was
studied, both in dry air and nitrogen,
for some complexes with ligands
derived from o-vanillin or 3,3‘-
dimethylbenzidine.