New “one-pot” Pd(II) and Zn(II) complexes of Schiff bases, derivatives of 1-amino-1-deoxy-d-sorbitol: Spectroscopic studies and biological and catalytic activities

Article abstract of DOI:10.1002/aoc.5485

New Pd(II) and Zn(II) Schiff base complexes, derivatives of various salicylaldehydes and 1-amino-1-deoxy-d-sorbitol, synthesized in one step, have been investigated using TG, NMR, UV–Vis, and IR spectroscopy. Zinc(II) complexes show antifungal activity against Candida albicans and Aspergillus niger, while palladium(II) complexes show catalytic activity in Heck reaction of styrene and bromobenzene.

Full text of DOI:10.1002/aoc.5485

Received: 4 November 2019
DOI: 10.1002/aoc.5485
Revised: 17 December 2019
Accepted: 17 December 2019
C O M M U N I C A T I O N
New “one-pot” Pd(II) and Zn(II) complexes of Schiff bases,
derivatives of 1-amino-1-deoxy-D-sorbitol: Spectroscopic
studies and biological and catalytic activities
A. Szady-Chełmieniecka1 | A. Rzuchowska1 | A. Markowska-Szczupak2
|
W. Schilf3 | Z. Rozwadowski1
1Department of Inorganic and Analytical
New Pd(II) and Zn(II) Schiff base complexes, derivatives of various
salicylaldehydes and 1-amino-1-deoxy-D-sorbitol, synthesized in one step, have
been investigated using TG, NMR, UV–Vis, and IR spectroscopy. Zinc(II) com-
plexes show antifungal activity against Candida albicans and Aspergillus niger,
while palladium(II) complexes show catalytic activity in Heck reaction of sty-
rene and bromobenzene.
Chemistry, Faculty of Chemical
Technology and Engineering,, West
Pomeranian University of Technology,
Szczecin, al. Piastów 42, 71-065 Szczecin,
Poland
2Department of Chemical and Process
Engineering, Faculty of Chemical
Technology and Engineering, West
Pomeranian University of Technology,
Szczecin, Szczecin, al. Piastów 42, 71-065
Szczecin, Poland
K E Y W O R D S
amino sugars, Pd(II) complexes, Schiff bases, Zn(II) complexes
3Institute of Organic Chemistry, Polish
Academy of Sciences, ul. Kasprzaka 44,
01-224 Warsaw, Poland
Correspondence
Z. Rozwadowski, Department of Inorganic
and Analytical Chemistry, Faculty of
Chemical Technology and Engineering,
West Pomeranian University of
Technology, Szczecin, al. Piastów
42, 71-065 Szczecin, Poland.
Email: zroz@zut.edu.pl
1 | INTRODUCTION
amino sugars, amino acids, and chitosan.[7,13–20] Identify-
ing new enantiomerically pure systems is one of the
Hugo Schiff, when published his paper “Eine neue Reihe
organischer Base” in 1864, did not know that com-
pounds named after his name will be so famous.[1] Schiff
base ligands are widely used in the synthesis of new
metal complexes. They are also extensively studied
because of their interesting binding ability and their
chemical and biological activities. Imines are formed as
intermediate products in biologically important reac-
tions.[2,3] Complexes of Schiff bases play an important
role in the detection of various ions,[4,5] exhibit biological
properties,[6–10] and are widely used as catalysts.[4,11,12]
Recently, several studies focused on Schiff bases and their
complexes, derivatives of natural products, for example,
major goals of organic chemistry. Although the number
of papers published on Schiff bases is increasing every
year, they still have a huge potential and are promising
ligands of metal complexes. Recently, Harohally et al.
reported antiaflatoxigenic and antimicrobial activities of
Schiff bases, derivatives of several substituted
salicylaldehydes and cinnamaldehyde and D-glucamine.
The presence of amino sugar moiety enhanced the biolog-
ical activity of compounds studied in comparison with
the control samples.[14] Cytotoxicity of copper(II),
nickel(II), and zinc(II) complexes of biopolymeric Schiff
bases, derivatives of salicylaldehydes and chitosan, were
tested with HeLa cells.[16] All complexes presented cell
Appl Organometal Chem. 2020;e5485.
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https://doi.org/10.1002/aoc.5485

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SZADY-CHEŁMIENIECKA ET AL.
viability higher than 50%, and zinc(II) complex was the
most soluble species in the series of studied complexes.
Palladium(II) complexes, derivatives of substituted
salicylaldehydes, showed a remarkable antimicrobial
activity against Bacillus subtilis, while palladium com-
plexes that are the derivative of 2-hydroxynaph-
thaldehyde showed an important antioxidant activity
and can be used as a sensor for detecting cholesterol
(limit of detection [LOD] value of 4.6μM).[20] Such
reports were the starting point to our studies. To the best
of our knowledge, most studies on complexes of amino
sugar Schiff bases deal sugars deal with compounds con-
taining moiety other than D-glucamine and rather in
ring form.[13,15] Only a few studies deal with compounds
containing sugar chain moiety,[14,18–23] and therefore D-
glucamine as a reactant in the synthesis of Schiff bases
is an unexplored chiral raw material. Our primary aim
was a convenient “one-pot” synthesis of new optically
active zinc(II) and palladium(II) complexes, derivatives
of natural products such as D-glucamine; their spectro-
scopic characterization; and preliminary tests for biologi-
cal and catalytic activities. Herein, we discuss the
influence of the formation of zinc(II) and palladium(II)
complexes on the chemical shifts in the NMR spectra in
solution and in solid state, and report the catalytic activ-
ity of palladium(II) complexes in the reaction between
bromobenzene and styrene, and the antifungal activities
of new complexes against Candida albicans, Aspergillus
niger, and Penicillium chrysogenum, as well as the
antibacterial activities against Escherichia coli and Staph-
ylococcus epidermidis. One-step synthesis allows us to
obtain optically pure and stable active zinc(II) and
palladium(II) complexes of Schiff bases, derivatives of
1-amino-1-deoxy-D-sorbitol, according to the rules of
“green chemistry.”
FIGURE 1 Studied complexes of N-(R-salicylidene)-1-amino-
1-deoxy-D-sorbitols (1–9)
results and specific rotation, is presented in the
supporting information.
2.2 | Measurements
The 1H and 13C NMR spectra were recorded using
BRUKER DPX-400 and DRX-500 spectrometers at room
1
temperature in DMSO-d6 solution. H and 13C chemical
shifts were referred to internal Tetramethylsilane (TMS),
and 15N chemical shifts were referred to external nitro-
methane as standards. The 1H and 13C signals were
assigned based on the analysis of 2D NMR spectra
(HMBC and HMQC). Typical concentration of the sam-
ples was 0.1 M. The CP MAS spectra were recorded using
a Bruker Avance 500 spectrometer using 4 mm MAS
H/BB probehead. Cross-polarization sequence was run
using ramped proton pulse and continuous wave
(CW) heteroatom irradiation. In both carbon and nitro-
gen solid state measurements, glycine was used as a pri-
mary standard. Then, the chemical shifts were
recalculated to TMS (13C) and nitromethane (15N) scales.
The diffuse reflectance FT-IR spectra were measured
using Bruker Alpha equipped with a platinum ATR sin-
gle reflection diamond-sampling module (Bruker Optics).
Thermogravimetric analysis was performed using TG
209 F1 Libra from NETZSCH. Samples of ca. 5 mg were
heated from 25 to 1000ꢀC with a heating rate of
10ꢀC/min in air.
2 | EXPERIMENTAL
2.1 | Materials
All salicylaldehydes and 1-amino-1-deoxy-D-sorbitol were
supplied by Sigma-Aldrich and EtOH by Chempur (PL).
Palladium(II) and zinc(II) complexes of the
glucamine Schiff bases (2–3, 5–6, 8–9) (Figure 1) were
prepared by “one-step” reaction. A mixture of 1-amino-
1-deoxy-D-sorbitol, aldehyde, and zinc(II) acetate
dihydrate or palladium(II) acetate in the ratio 2:2:1 in
absolute EtOH solution was refluxed for 2 h giving a solid
pale yellow (zinc[II] complexes) or yellow (palla-
dium[II] complexes) precipitate. Complete assignment of
the NMR signals in DMSO-d6 solution, IR bands, UV–Vis
bands, and DTA–TG data, as well as elemental analyses’
UV–Vis absorption spectra were measured using a
Jasco 670 spectrometer in a 10 mm quartz cell. The con-
centrations of DMSO (spectral grade, Chempur, PL) solu-
tions for all compounds studied were in the range 10−4
10−5M.
–
Elemental analyses (EA) were performed using an
Elementar Vario III analyzer. GC–MS spectra were
recorded using HP 6890 with HP 5973 mass detector and
HP 19091S-433 capillary column. Conditions: initial oven
temperature, 50ꢀC; final temperature, 300ꢀC; rate,
10ꢀC/min; run time, 43 min; injection volume, 2.0 μL.

SZADY-CHEŁMIENIECKA ET AL.
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The specific rotation of the studied compounds was
investigated using Polarymetr Autopol IV from Rudolph
Research Analytical in DMSO solution (~0.001 g/cm3).
The conditions of Heck reaction were: a mixture of
1 mmol styrene (0.115 cm3), 1.25 mmol bromobenzene
(0.3 cm3), 2.5 mmol base, and 0.05 mol% of the respective
palladium catalyst, as well as 5 cm3 DMF, was placed in
a round bottom flask equipped with a magnetic stirrer
and heated in range from 100 to 130ꢀC for 6 h. The yield
of the reaction was established based on GC–MS or NMR
spectra. The separation of signals assigned to reactants
and products in 1H NMR spectra allowed to establish the
conversion of styrene. The proposed method was based
3 | RESULTS AND DISCUSSION
Owing to the very low solubility of the obtained com-
pounds in common organic solvents, it was not possible
to obtain a crystal suitable for X-ray spectroscopy. The
structure of new complexes was confirmed by elemental
analysis and NMR, FT-IR, UV–Vis spectroscopy, and
DTA–TG.
Based on elemental analyses and synthesis route, a
stoichiometry ratio of 2:1 (ligand/metal) was proposed
for both types of complexes (Figure 1). Elemental analysis
and DTA–TG (supporting information) revealed the pres-
ence of two water molecules in zinc(II) complex only for
compound 5.
1
on the integration of selected signals in H NMR spectra
without any special treatment of the reaction mixture
and addition of deuterated solvents (external lock only).
The differences between results calculated using GC–MS
and NMR were only 1–2%.
3.1 | NMR spectroscopy
3.1.1 | Ligands
The antimicrobial tests were performed with the
gram-negative bacteria E. coli strain K12 (ATCC 25922),
gram-positive bacteria S. epidermidis (ATCC 49461),
candidiasis-causing yeast—C. albicans (isolated from
patients with immunodeficiency disorders), and mold
fungi A. niger and P. chrysogenum (isolated from air). All
fungi originated from IIChTEE collection. The antimicro-
bial activity of Schiff bases was preliminarily investigated
using disk diffusion method. Plate count agar
(BioMaxima S.A., PL) for E. coli, brain heart infusion agar
(BioMaxima S.A., PL) for S. epidermidis, sabouraud dex-
trose agar (BTL Sp. Z.o.o., PL) for C. albicans, and malt
extract agar (Merck, PL) were used. The 24-h microbial
cultures in liquid media were centrifuged at about
1000 rpm for 10 min. Then, the entire sediment was
transferred to a sterile bottle containing 0.85% sodium
chloride buffer. Microbial culture was appropriately
diluted to obtain an inoculation level 0.5 in MacFarland
Standards (BioMerieux, France) corresponding to cell
density of approximately 1.5 × 108 CFU/mL. Next, sterile
plastic petri dishes (Ø = 9.0 cm) with appropriate media
were inoculated with 0.25 mL microorganism suspen-
sions. The sterile paper disks (Whatman No. 1, diameter
6.0 mm) impregnated with the obtained Schiff bases
(concentration 10 mg/mL in DMSO, 10 μL/disk) were
placed at different locations on the surface of the culture
plates and incubated at 37ꢀC for 24 h for bacteria and
25ꢀC for 72 h for fungi. The zone of inhibition around
the paper disks was measured. Sensitivity to the tested
agents was classified by the diameter of the inhibition
halos as: not sensitive (−) for diameters 6 mm; sensitive
(+) for diameters 7–15 mm; very sensitive (++) for diam-
eters 16–25 mm, and super sensitive for diameters
>25 mm (+++). Two disks per plate were used, and each
plate was set up in triplicate.
1
Complete assignment of H and 13C signals for the stud-
ied compounds 1–9 in solutions are presented in Table S2
(supporting information). The selected values of NMR
chemical shifts in solution and in solid state for impor-
tant positions are presented in Table 1. The values of
δOH and the position of the 15N signals of DMSO-d6 solu-
tion were similar to those observed for other amino sugar
Schiff bases, which indicated the presence of medium-
strength intramolecular hydrogen bond and proton trans-
fer equilibrium.[23–25] Large differences in CP MAS NMR
values between 15N and the solution of DMSO-d6 (up to
ca. 90 ppm) indicated the shift of the equilibrium strongly
toward the proton-transferred form in the solid state. The
studied ligands in the solid state existed mainly in NH
form. Such a behavior was observed for other Schiff
bases.[26,27] The differences between the chemical shifts
of 13C in solution and in solid state observed for other
atoms were much smaller.
3.1.2 | Zn(II) and Pd(II) complexes
The disappearance of the hydrogen-bonded OH signals
(ca. 14–15 ppm) indicated the coordination of the metal
ions in compounds 2–3, 5–6, and 8–9. Other positions in
1H NMR spectra (Table S1 and Table 1) were also
affected by the complex formation, in particular, H-10 in
palladium(II) complexes (up to ca. 1 ppm). In general,
the formation of palladium(II) complexes has stronger
influence on the position of signals in 1H NMR spectra in
comparison with the formation of the zinc(II) complexes.
Changes in 13C and 15N chemical shifts clearly indi-
cated the formation of zinc(II) and palladium(II)

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SZADY-CHEŁMIENIECKA ET AL.
TABLE 1 Selected 13C and 15N chemical shifts for compounds
studied (1–9) in solution (DMSO-d6) and in solid state (CP MAS) in
ppm
Compound
NMR
C-2
C-7
N
(1) (5-Br)
DMSO-d6
161.3
170.0
163.1
166.1
163.7
156.7
178.6
176.4
167.8
167.3
167.4
162.8
160.8
169.7
162.8
165.5
169.3
162.2
166.2
169.3
163.4
167.8
169.1
163.8
165.5
171.7
161.8
159.6
162.9
175.1
170.7
164.9
163.9
169.1
172.8
172.1
163.9
162.6
−94.7
(2)
−138.3
−175.5
−171.2
−132.5
−173.2
−194.8
−130.3
−172.8
−164.8
−147.3
−169.5
−177.5
−219.1
−147.5
−149.8
−181.0
−182.4
−202.8b
−149.3c
−154.0
−170.2d
−172.2
(3)
(4)a (3,5-diCl)
(5)
(6)
(7)(5-NO2)
(8)
(9)
(1) (5-Br)
(2)
CP MAS
(3)
(4) (3,5-diCl)
(5)
(6)
156.3
(7) (5-NO2)
(8)
180.1
174.1
173.6
167.9
167.7
FIGURE 2 Chemical shifts of compounds studied in DMSO-
d6. Influence of the Zn(II) and Pd(II) complex formation on (a) C-2
and (b) C-7
(9)
ca. −4 ppm for 5 up to ~4 ppm for 9. The large differences
between the values of δN chemical shifts for zinc(II) and
palladium(II) complexes in DMSO-d6 equal ca. 40 ppm
suggested that the nitrogen lone pair in palladium com-
plexes is strongly engaged in the metal ion coordination
than that in zinc complexes (Figure 3).
aData from [23]
.
b−12.0 ppm (5-NO2).
b−12.2 ppm (5-NO2).
c−11.9 ppm (5-NO2).
complexes of the respective Schiff bases. The magnitude
and the direction of changes of chemical shifts were simi-
lar to those observed for other Schiff bases after the for-
mation of the metal coordination bonds.[28–32]
Comparison of the 13C and 15N chemical shifts of zinc(II)
and palladium(II) complexes in the solution reflected dif-
ferences in ionic radii among the respective metal
ions.[33] The formation of the complexes shifted the posi-
tions of the C-2, C-7, and nitrogen signals (Table 1).
Zinc(II) complexes deshielded C-7 carbons and shielded
nitrogen (except 2), while palladium(II) complexes
shielded C-2 and C-7 carbons (Figure 2). The differences
between δC-2 values for ligand and zinc(II) complexes
were from ca.−9 for 2 to ~3 ppm for 5, while those for
palladium(II) complexes were from ca. 11 ppm for 9 to
~2.0 ppm for 3. Smaller changes were observed for
methine carbon (C-7) in both types of complexes: from
In CP MAS spectra, differences between the δN chem-
ical shifts of zinc(II) and palladium(II) complexes, deriva-
tives of the same ligands, were also observed and found
to be ca. 20–30 ppm. The position of the 13C CP MAS sig-
nals for methine carbons C-7 and C-2 (Figure 5) also
reflected differences between coordination of the zinc(II)
and palladium(II) ions in complexes studied and were
close to 10 and 5 ppm, respectively (Table 1, Figure 4).
3.2 | UV–Vis and IR spectroscopy
UV–Vis measurements were performed for compounds
1–9. The UV–Vis bands of the studied N-(R-salicylidene)-
1-amino-1-deoxy-D-sorbitols and their zinc(II) and
palladium(II) complexes are presented in Table S3
(supporting information). For ligands, a low energy band

SZADY-CHEŁMIENIECKA ET AL.
5 of 8
TABLE 2 Selected FT-IR bands of studied Schiff bases (1–9)
Compound
v(OH)
3310 br
3427 br
3344 br
3450 br
3298 br
3295 br
3326 br
3289 br
3293 br
3410 br
3296 br
3447 br
3313 br
v(C=N)
v(Me-O)
v(Me-N)
(1) (5-Br)
1633s
–
–
(2)
1625s
462s
416s
(3)
1618s
1639s
1629s
1625s
1653s
464s
–
421s
–
(4) (3,5-diCl)
(5)
483s
489s
–
410s
418
–
(6)
7 (5-NO2)
FIGURE 3 Influence of Zn(II) and Pd(II) complex formation
on 15N NMR chemical shifts of compounds studied in DMSO-d6
(8)
(9)
1634s
1630s
462s
465s
415s
424s
br broad.
s sharp.
vibration toward lower frequencies due to the coordina-
tion of the metal ion to the nitrogen confirmed the for-
mation of the corresponding complexes.[6–8,29,30,34] Also
sharp bands in the range 1460–1200 cm−1 after the coor-
dination of the metal indicated a change of the structure
and complex formation. The position of the bands
assigned to the OH group changed only slightly due to
the presence of the several OH groups of sugar moiety.
FIGURE 4 Influence of the Zn(II) and Pd(II) complex
formation on C-2 chemical shifts in CP MAS NMR spectra of
compounds studied
3.3 | Specific rotation
All studied compounds were optically active, and there-
fore their optical properties are also important. The spe-
cific rotation of compounds studied in DMSO is
summarized in Table S4 (supporting information). Spe-
cific rotation was stable over time. The values of [α] were
in the range from −14.15o for compound 1 to −270.3o for
compound 8. The coordination of palladium(II) has more
impact on chirality center in comparison with that of
zinc(II). For all palladium(II) complexes, [α] values were
above −250o (much more than for ligands), while for
zinc(II) complexes, [α] values were rather close to the
values measured for pure ligands (Figure 5).
at ~400 nm assigned to the NH form and high energy
bands at ~300 nm and ca. 260 nm assigned to the OH
form were observed.[23] Coordination of the zinc(II) and
palladium(II) caused the disappearance of the band at
~400 nm and bathochromic shift of the one of the high
energy bands to ~390 nm, typical of complex
formation.[6,8,29,30]
FT-IR spectra of the ligands showed sharp bands at
ca. 1630 cm−1 and ca. 1600 cm−1 (Table 2 and supporting
information) in the region typical for v(C=N) vibration
coupled with v(C=C) vibrations.[6–8,23,29,30,34] Broad
absorption bands at ca. 3500–3300 cm−1 were assigned to
the intramolecularly bonded HX group and OH groups of
sugar moiety. A comparison of the spectra of compounds
studied showed that complex formation strongly
influenced the position of several bands and the appear-
ance of new ones. In particular, new bands at ca. 420–410
cm−1 and ca. 480–460 cm−1 assigned to v(Me-O) and
v(Me-N), respectively, and the shift of the v(C=N)
3.4 | Biological activity
One of the reasons for the synthesis of new Schiff base
complexes, derivatives of amino sugar, was their poten-
tial for biological activity.[6–10,14,17,28] According to Silva
et al.,[35] Schiff bases are promising candidates for the

6 of 8
SZADY-CHEŁMIENIECKA ET AL.
C. albicans was more sensitive to all tested substances.
The best overall antimicrobial activity presented
complex 8.
3.5 | Catalytic activity
Palladium complexes of Schiff bases are widely used as
catalysts in Heck reaction.[37] We also performed some
preliminary tests of the catalytic activity of the new
complexes (Figure 1). The results of the catalytic activity
in the reaction between styrene and bromobenzene are
presented in Table 4. For each complex, the reaction
condition was repeated three times, and the average
values are presented in Table 4. However, variation in
the yields was observed. All palladium(II) complexes
were active catalysts in the reaction between styrene
and bromobenzene at temperatures above 120ꢀC. The
yields of trans-stilbene as a main product were in the
range ~15–78%—with the highest being observed for the
derivative of 5-nitrosalicylaldehyde and the lowest for
halogen derivatives. Higher temperatures increased the
yield of Heck reaction. For complex 3, the conversion of
styrene increased from 35% at 120ꢀC to 74% at 130ꢀC.
The type of base used [K2CO3 or N(Et)3] had some
influence on the yield of the reaction. Usually N(Et)3
allowed for a shorter reaction time; however, at higher
temperatures N(Et)3 decomposed. We also observed
some variation of the yield (up to 8%) due to the hetero-
geneous nature of the reaction and the intensity of
mixing when K2CO3 was used. In general, only traces
(ca. 2–5%) of the byproduct cis-stilbene was found in the
reaction mixture. Low conversion was due to the higher
yield of the byproduct (cis-stilbene). The yield of cis-
FIGURE 5 Comparison of the specific rotation between
ligands (L) and zinc(II), and palladium(II) complexes
design of new antifungal agents. They can form hydrogen
bonds through the imine group, inhibit the activity for
metabolic pathways of enzymes, or disrupt the outer
membranes and impair the transport of nutrients.[36] For
all compounds studied, preliminary antibacterial and
antifungal tests were performed against selected strains
of microorganisms (Table 3). The obtained results indi-
cated that the antimicrobial activity of the tested Schiff
bases depends on the type of microorganism and the
chemical composition of the compounds. Unexpectedly,
the presence of the chain form of sugar moiety in com-
plexes studied had rather little antibacterial properties
against gram-negative E. coli and gram-positive
S. epidermidis (Table 3). Zinc(II) complexes 5 and
8 inhibited the growth of fungi of clinical interest, such
as A. Niger. Compounds 4, 5, and 7 effectively inhibited
the growth of P. chrysogenum. Interestingly, yeast
TABLE 3 Antimicrobial activity of compounds (1–9)
Microorganism sensitivitya
Compound
E. coli
S. epidermidis
C. albicans
P. chrysogenum
A. niger
(1) (5-Br)
+
+
−
−
+
+++b
−
−
(2)
+
−
−
+
(3)
−
−
−
(4) (3,5-diCl)
++
+
−
−
+
+++b
+++
++
−
n.t.
+
(5)
+
+
++
+
−
(6)
+
−
(7) (5-NO3)
+
+
−
+
++
+
n.t.
+
(8)
(9)
+++
+
−
−
n.t., not tested.
aNot sensitive (−), sensitive (+), very sensitive (++), super sensitive (+++).
bZone of inhibition larger than 40 mm.

SZADY-CHEŁMIENIECKA ET AL.
7 of 8
TABLE 4 Catalytic activity of palladium(II) complexes in Heck reaction
Compound
Base
Temp. (ꢀC)
130
Time (h.)
Conversion (%)
Yield of trans-stilbene (%)
Yield of cis-stilbene (%)
5-Br (3)
K2CO3
N(Et)3
N(Et)3
K2CO3
N(Et)3
N(Et)3
K2CO3
N(Et)3
6
6
3
6
3
6
6
3
51
74
35
64
28
29
79
69
45
72
30
61
16
16
76
68
6
2
130
120
5
3,5-diCl (6)
5-NO2 (9)
130
3
120
12
13
3
100
130
130
~1
stilbene increased up to ~13% when the conversion of
the styrene was 28%. For the studied palladium(II) com-
plexes, long-lasting activity in the reaction mixture was
also tested. After adding the initial amount of substrates
to the reaction mixture, the conversion decreased
ca. 20%. A further addition of the substrates lowered the
conversion by another 10%.
exhibited catalytic activity in Heck reaction between
bromobenzene and styrene.
ORCID
Z. Rozwadowski https://orcid.org/0000-0001-9504-9381
REFERENCES
[1] H. Schiff, Justus Liebigs Ann. Chem. 1864, 131-132, 118.
[2] M. Chan-Huot, S. Sharif, P. M. Tolstoy, M. D. Toney, H.-
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[3] P. Christen, D. E. Metzler, Transaminases, 1st ed., Wiley &
Sons, New York, NY, USA 1985 37.
3.6 | TG–DTA
The TG–DTA curves confirmed the presence of two mol-
ecules of water in complex 5. The TG curve showed the
initial dehydration process (mass change 3.65% at 83.2ꢀC
for this compound only (supporting information). All
complexes studied were stable up to ~217–270ꢀC. Above
this temperature range, the decomposition process, either
for zinc(II) or for palladium(II) complexes, started.[10,34]
The decomposition of the complexes was completed
approximately at 600–700ꢀC; an exception was observed
for compound 9, which decomposed at 320ꢀC. Residual
masses, in the range 4.22%–17.7%, at 900ꢀC, confirmed
the formation of the complexes and were similar to those
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4 | CONCLUSIONS
New “one-pot” synthesized palladium(II) and zinc(II)
complexes of amino sugar Schiff bases were characterized
using spectroscopic methods. All complexes had a stoi-
chiometry ratio of 2:1 (L/Me), but had different chirality
centers as indicated by the different values of specific
rotation. NMR data reflect the differences in ionic radii
among zinc(II) and palladium(II) the complexes. Zinc(II)
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SUPPORTING INFORMATION
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Organometal Chem. 2020;e5485. https://doi.org/10.
1002/aoc.5485