Polymer complexes. LXXVIII. Synthesis and characterization of supramolecular uranyl polymer complexes: Determination of the bond lengths of uranyl ion in polymer complexes

Article abstract of DOI:10.1002/aoc.5153

The UO₂(II) polymer complexes (1–5) of azo dye ligands 5(4`-derivatives phenylazo)-8-hydroxy-7-quinolinecarboxaldehyde (HL_x) were prepared and characterized by elemental analysis, ¹H NMR, IR spectra, thermal analysis and X-ray diffraction analysis (XRD). The molecular geometrical structures and quantum chemical of the ligands (HL_x) and their tautomeric forms (D and G) were calculated. Molecular docking between the HL_x ligands and their tautomeric form with two receptors of the breast cancer (1JNX) and the prostate cancer (2Q7K) was discussed. From the histogram of the HOMO–LUMO energy gap (ΔE) and the estimated free energy of binding of the receptors of prostate cancer (2Q7K) and breast cancer (1JNX) for the ligands (HL_x), it is observed that the ΔE values of the ligands (HL_x) increases in the order HL₂?3?4?1?5. The electronic structures and coordination were determined from a framework for the modeling of the formed polymer complexes. From the IR spectra of the polymer complexes, the symmetric stretching frequency υ₃ values of UO₂ ²⁺ were used for the determination of the force constant (F_U-O (in 10^?8?N/?)) and the bond length (R_U-O (?)) of the U–O bond by using Wilson, G. F. matrix method, McGlynn & Badger's formula and El-Sonbati equations. The plot of the bond distance r_U-O (r₁, r₂, r₃, and r_t) vs. υ₃ was showed straight lines with increase in the value of υ₃ and decrease in r_U-O.

Full text of DOI:10.1002/aoc.5153

Received: 21 May 2019
DOI: 10.1002/aoc.5153
Revised: 11 July 2019
Accepted: 13 July 2019
F U L L P A P E R
Polymer complexes. LXXVIII. Synthesis and
characterization of supramolecular uranyl polymer
complexes: Determination of the bond lengths of uranyl ion
in polymer complexes
M.A. Diab1
| S.G. Nozha2 | A.Z. El‐Sonbati1
| M.A. El‐Mogazy1 | Sh.M. Morgan3
1 Chemistry Department, Faculty of
Science, Damietta University, Damietta,
Egypt
2 Domyat Laboratory, Ministry of Health,
Damietta, Egypt
The UO2(II) polymer complexes (1–5) of azo dye ligands 5(4`‐derivatives
phenylazo)‐8‐hydroxy‐7‐quinolinecarboxaldehyde (HLx) were prepared and
1
characterized by elemental analysis, H NMR, IR spectra, thermal analysis
and X‐ray diffraction analysis (XRD). The molecular geometrical structures
and quantum chemical of the ligands (HLx) and their tautomeric forms
(D and G) were calculated. Molecular docking between the HLx ligands and
their tautomeric form with two receptors of the breast cancer (1JNX) and the
prostate cancer (2Q7K) was discussed. From the histogram of the HOMO–
LUMO energy gap (ΔE) and the estimated free energy of binding of the recep-
tors of prostate cancer (2Q7K) and breast cancer (1JNX) for the ligands (HLx),
it is observed that the ΔE values of the ligands (HLx) increases in the order
HL2 < HL3 < HL4 < HL1 < HL5. The electronic structures and coordination
were determined from a framework for the modeling of the formed polymer
complexes. From the IR spectra of the polymer complexes, the symmetric
3 Environmental Monitoring Laboratory,
Ministry of Health, Port Said, Egypt
Correspondence
Sh.M. Morgan, Environmental Monitoring
Laboratory, Ministry of Health, Port Said,
Egypt.
Email: shimaa_mohamad2010@yahoo.
com
2+
stretching frequency υ3 values of UO2 were used for the determination of
the force constant ( F U‐O (in 10−8 N/)) and the bond length (RU‐O ()) of the
U–O bond by using Wilson, G. F. matrix method, McGlynn & Badger's formula
and El‐Sonbati equations. The plot of the bond distance rU‐O (r1, r2, r3, and rt)
vs. υ3 was showed straight lines with increase in the value of υ3 and decrease in
rU‐O
.
KEYWORDS
molecular docking, molecular geometrical structures, polymer complexes, quantum chemical
parameters, thermal decomposition analyses
1 | INTRODUCTION
they have been used in chromatography and for the detec-
tion of metal ions, antioxidant and biological effect activi-
Literature surveys indicate that quinoline derivatives
possess diverse pharmacological activities, including anti‐
inflammatory, antiviral, antitumor activities antimicrobial
and, antibody titer against bovine respiratory syncytial
(BRS) virus in serum neutralizations test (SNT).[1–6] Also,
ties.[7–9] The chemistry of transition metal complexes of
8‐hydroxyquinoline has received much attention as their
rational design and synthesis in coordination chemistry,
also because of their potential applications as functional
materials and in bioinorganic chemistry.
Appl Organometal Chem. 2019;e5153.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
1 of 16
https://doi.org/10.1002/aoc.5153

2 of 16
DIAB ET AL.
Quinolines compounds are considered as the major
2 | EXPERIMENTAL
2.1 | Materials
class of heterocyclics that are found in many biologically
active natural products and synthetic molecules and
quinoline derivative compounds are known to be the best
chelating agents.[5,10] They form very stable chelate rings
with metal centers, and very stable complexes with a
number of metal ions. The deprotonated oxygen atom
and the ring nitrogen atom are involved in the metal
chelation.[5,6]
8‐Hydroxyquinoline moiety has received considerable
attention due to their efficient ionospheres, therapeutic
and fluorescence properties.[11–13] The parent aldehyde,
7‐formyl‐8‐hydroxyquinoline, used in the present study
as its azo dye derivative for the preparation of five
asymmetrical azo dye ligands was previously used to pre-
pare its own metal complexes. The coordination com-
plexes of bivalent transition and non‐transition metals
was an interesting topic because of a Scaffold and supra-
molecular skeleton, beautiful artistic, spectacular geome-
try, captivating functional property, and high thermal
stability.[14–18] Coordination chemistry of multidentate
ligands with transition metals offers versatility attraction
from supramolecular structures, functional aspects, and
remarkable applications in the branch of solid state
chemistry.[19–24]
Polymer science was emerged as active branch of
materials science. This field impinges on areas of com-
modity, engineering and specialty polymers thereby stim-
ulating interest all over the globe in exploiting newer
domains. This emerged branch is polymer metal com-
plexes with organic polymer containing coordinating
sites, complexed with metals. The research on coordina-
tion polymers has been constantly developed in past
years. They have excellent properties as treatment of
wastewater, semiconducting catalytic properties, in metal
recovery, in protective coating, as antifouling paints and
anti‐fungal properties.[10,25–27]
Uranyl polymer complexes of ligands (HLx) are syn-
thesized and characterized by using various spectroscopic
techniques for identifying its structures and geometries.
The geometrical studies of the ligands (HLx) and their
tautomeric forms are optimized theoretically. Molecular
docking between form ligands (HLx) and their tautomeric
form with two types of proteins is studied. Study the rela-
tion between molecular geometrical structures and
molecular docking. Determination the stretching and
interaction force constants from which the U‐O bond dis-
tances is calculated. Also, the thermal analysis data per-
mit us to obtain information regarding the structure
elucidation. The thermodynamic‐kinetic parameters of
polymer complexes are calculated by using the Coats‐
Redfern and Horowitz‐Metzger methods to confirm the
stability of them.
All chemicals used in this study were of pure grade and
of highest purity available were used without further
purification. The chemicals used included aniline or p‐
substituted derivatives and 8‐hydroxyquinoline (Sigma),
UO2(NO3)2.6H2O and organic solvents included ethanol,
methanol and dimethylformamide (DMF). were spectro-
scopically pure from BDH Chemical Ltd. Hydrochloric
acid, sodium nitrite, sodium hydroxide, potassium hydrox-
ide and sodium acetate (AR) were used without further
purification. Elemental analyses (C, H, and N) were car-
ried out at the Microanalytical Unit of Cairo University.
The percentages of uranium content of each complex were
determined by igniting a definite mass of the sample at
1000 °C and weighing the residue. Infrared spectra were
recorded in the form of KBr discs using a Pye Unicam Sp
1
2000 spectrophotometer. H NMR spectra were obtained
on a JEOL Fx 900Q Fourier transform spectrometer using
DMSO‐d6 as solvent and tetramethylsilane (TMS) as inter-
nal reference. The magnetic moment of the prepared solid
complexes was determined at room temperature using
Gouy method. Mercury (II) tetrathiocyanatocobalt (II)
[Hg{Co (SCN)4}]. Diamagnetic corrections were calculated
from the values given by Selwood[28] using Pascal's con-
stants. Thermal studies were performed on Simultaneous
Thermal Analyzer (STA) 6000 and the thermal properties
of the samples were carried out in the temperature range
from 30 to 800 °C at the heating rate of 10 °C/min under
dynamic nitrogen atmosphere. X‐ray diffraction analysis
of compounds was recorded on X‐ray diffractometer anal-
ysis in the range of diffraction angle 2θo = 4–80o[29–32]
using CuKα radiation. The tube applied voltage and cur-
rent are 40 kV and 30 mA, respectively.
The molecules were built with Perkin Elmer
ChemBio3D software[30,33,34] and the quantum chemical
parameters such as the highest occupied molecular
orbital energy (EHOMO), the lowest unoccupied molecular
orbital energy (ELUMO) and HOMO‐LUMO energy gap
(ΔE*) for the tautomeric forms (A, D and G) of the
ligands (HLx) were calculated. The El‐Sonbati equation
was manipulated using a computer program developed
in our laboratories using the C Language. Molecular
docking calculations of the binding between the receptors
of the breast cancer (1JNX Gene regulation) and the
prostate cancer (2Q7K Hormone) protein models were
carried out. The MMFF94 Force field was used for energy
minimization of the ligand molecules using Docking
Server.[34–36] Auto Dock parameter set‐ and distance‐
dependent dielectric functions were used in the calcula-
tion of the van der Waals and electrostatic terms.

DIAB ET AL.
3 of 16
collected by filtration and washed with a cold water–
methanol mixture to remove the unreacted uranyl salts,
followed by overnight vacuum drying. The purity of the
formed polymer components was examined by TLC to con-
firm the reaction of the ligands with UO2(NO3)2. 6H2O.
The inherent viscosities (inh = ln r/C); C = 0.5 g dl−1) mea-
sured with a Desreux‐Bishoff suspended level viscometer
at 30 °C 0.001 °C, using dimethylsulphoxide (DMSO)
as solvent are found to be in the range 1.35–1.54 for the
polymer complexes (1–5), respectively. The analytical data
of all polymer complexes are collected.
2.2 | Synthesis of the ligands (HLx)
Aniline or p‐substituted derivatives (1 mmol) (1a) was dis-
solved in 30 ml of ethanol. Concentrated hydrochloric
acid (10 ml) was diluted with about 40 g of crushed ice
and then dropwise addition of the aniline or p‐substituted
derivatives solution to the crushed ice.[15,17] To this cold
solution addition of 10% sodium nitrite (1 mmol) and
stirred for about 1 hr to complete diazotization (2a). The
coupling agent 8‐hydroxy‐7‐quinolinecarboxaldehyde
(1 mmol) (3a) dissolved in 50 ml of ethanol containing
(1.0 mmol) of potassium hydroxide was then added to
the cold mixture. The resulting solution was stirred well
and sodium acetate (3 g) was added for neutralization.
The ligands (HLx) were washed with ethanol and col-
The polymer complexes {[UO2(Lx)(OH2)]}n (1–5) of
ligands (HLx) were prepared as follows:
ÈÂ
ÃÉ
UO2ðNO3Þ2:6H2O þ HLx
→
UO2ðLxÞ2ðOH2Þ
n
ÈÂ
ÃÉ
UO2ðL1Þ2ðOH2Þ ð1Þ:Anal:Calcd for UðC34H26N6O9Þ ð%Þ:C; 45:33; H; 2:89; N; 10:71; U; 26:44:Found ð%Þ:
n
C; 45:14; H; 2:78; N; 10:50; U; 26:22:
ÈÂ
ÈÂ
ÃÉ
UO2ðL2Þ2ðOH2Þ
UO2ðL3Þ2ðOH2Þ
ð2Þ:Anal:Calcd for UðC34H26N6O7Þ ð%Þ:C; 47:01; H; 3:00; N; 9:68; U; 27:42:Found ð%Þ:
C; 46:89; H; 2:88; N; 9:47; U; 27:24:
n
n
ÃÉ
ð3Þ:Anal:Calcd for UðC32H22N6O7Þ ð%Þ:C; 45:71; H; 2:62; N; 10:00; U; 28:33:Found ð%Þ:
C; 45:64; H; 2:53; N; 9:78; U; 27:88:
ÈÂ
ÈÂ
ÃÉ
ÃÉ
UO2ðL4Þ2ðOH2Þ
UO2ðL5Þ2ðOH2Þ
ð4Þ:Anal:Calcd for UðC32H20N6O7ClÞ ð%Þ:C; 42:24; H; 2:20; N; 9:24; U; 26:18:Found ð%Þ:
C; 42:11; H; 2:09; N; 9:04; U; 25:77:
n
n
ð5Þ:Anal:Calcd for UðC32H20N8O11Þ ð%Þ:C; 53:64; H; 2:76; N; 7:54; U; 32:87:Found ð%Þ:
C; 53:45; H; 2:55; N; 7:73; U; 32:57:
lected by vacuum filtration. The preparation is shown in
Figure S1.
3 | RESULTS AND DISCUSSION
3.1 | Characterization of the ligands (HLx)
2.3 | Synthesis of the polymer complexes
(1–5)
It has been found that the reaction of aniline or
p‐substituted derivatives (1a) with nitrous acid
(NaNO2/HCl) afforded the diazonium salt (2a), which
underwent coupling reaction with 8‐hydroxy‐7‐
quinolinecarboxaldehyde (3a) to yield the azo coupling
product (HLx). The reaction can be represented in
Figure S1.
To a solution of the ligands (HLx) (1 mmol) in mixture of
30 ml (2:1 v/v) of DMF and methanol (25 mL) solution of
UO2(NO3)2.6H2O (1 mmol) was slowly added with stirring
for 1 hr. The mixed solution was stirred for another ~ 2–
3 hrs under reflux. The solvent was removed to a half vol-
ume after the completing of the reaction and cooled down
to room temperature. The polymer complexes were
The IR spectra of the ligands (HLx) are devoid of the
bands due to the NH2 group of the p‐derivatives of aniline

4 of 16
DIAB ET AL.
and a band due to –N=N– group, the azo dye ligands
(HLx) linkage appeared. The IR spectra of the ligands
(HLx) show a medium‐broad band centered at ~ 3315–
3325 cm−1 due to υ (OH) and strong bands at ~ 1280–
1295 cm−1 δ (OH), due to intramolecular hydrogen
bond.[20] Similarly another medium intensity bands
attributable to the strongly hydrogen bonded. The spectra
of quinoline and Ar‐H rings appeared in the ~ 9.30–
7.23 ppm. The resonance signals at ~ 2.55 and ~
3.85 ppm are due to the methyl group attached to the
keto group and methoxy protons, respectively.
appearing at ~ 1271
8 cm−1 in the free ligands are
due to the υ(C‐O) stretching vibrations (Figure S2). The
C8‐OH group of the quinoline can form an intramolecular
hydrogen bond with the aldehydic‐O group (Figure S1(B)
and/or azomethine‐N group Figure S1(C)) while the
other form an intermolecular hydrogen bond with the
oxygen of the C8‐OH group, azomethine‐N or aldehyde‐
O of the another molecule (Figure S1(E & F)), as shown
in literatures of El‐Sonbati et al.[5] The band is slightly
affected by the nature and position of the substituent.
The υ(C=N) stretching vibration is observed in the form
3.2 | Theoretical studies of ligands (HLx)
and their tautomeric forms
The geometrical structures of the ligands (HLx) (Figure
S1(A)) and their tautomeric forms (D and G) are opti-
mizes and shown in Figures 1–5. The lowest unoccupied
molecular orbital energy (ELUMO), the highest occupied
molecular orbital energy (EHOMO), the energy gab
(HOMO–LUMO energy gap (ΔE)) between them values
and the other quantum chemical parameters are listed in
Table 1. The values of ΔE which are an important stabil-
ity index, is applied to develop theoretical models for
explaining the structure and conformation barriers in
many molecular systems.[30,36,37] The values of the energy
gab (ΔE) for the ligands (HLx) (Figure S1(A)) and their
tautomeric forms (D and G) confirmed to that the form
(G) is more stable than the other tautomeric forms (A
and D) (Table 1). Primary calculations reveal that the
tautomeric form (G) of ligands (HLx) is more stable than
ligands (HLx) (Figure S1(A)) and tautomeric form (D).
Figure 6 shows the HOMO and LUMO orbital's for tauto-
meric form (G) of ligands (HLx). The elected bond
of a band at ~1585
5 cm−1. The spectral region at ~
1600–1400 cm−1 is complicated because of the stretching
modes of –C=C‐ and –N=N‐ which are superimposed in
the same region.
The 1H NMR studies for the free ligands under investi-
gation in DMSO‐d6 show 9.16–12.25 ppm are assigned to
the OH protons of the quinolone ring. The existence of
the OH signal at high downfield of TMS due to strong
hydrogen bonding occurs between OH and the
azomethine nitrogen of quinoline moiety and/or CO
group as shown in Figure S1. This favors the formation
of an intramolecular hydrogen bond with the CO group.
The signal due to OH proton disappears in D2O solution
FIGURE 1 The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the tautomeric form
(G) of ligands (HLx)
FIGURE 2 The optimized molecular structures of the HL1 ligand and its tautomeric forms (D and G)

DIAB ET AL.
5 of 16
FIGURE 3 The optimized molecular structures of the HL2 ligand and its tautomeric forms (D and G)
FIGURE 4 The optimized molecular structures of the HL3 ligand and its tautomeric forms (D and G)
FIGURE 5 The optimized molecular structures of the HL4 ligand and its tautomeric forms (D and G)
TABLE 1 The calculated quantum chemical parameters of the ligands (HLx) and their tautomeric forms
Ligandsa Formsa EHOMO (eV) ELUMO (eV) ΔE (eV) χ (eV) η (eV) σ (eV)‐1 Pi (eV) S (eV)−1 ω (eV) ΔNmax
HL1
HL2
HL3
HL4
HL5
(A)
(D)
(G)
−4.820
−7.172
−4.928
−4.219
−4.043
−4.370
0.601
3.129
0.558
4.520
5.608
4.649
0.301
1.565
0.279
3.328
0.639
3.584
−4.5195 1.664
−5.6075 0.320
33.986
10.049
38.733
15.040
3.584
16.663
−4.649
1.792
(A)
(D)
(G)
−4.961
−7.175
−5.219
−4.423
−4.165
−4.725
0.538
3.01
0.494
4.692
5.670
4.972
0.269
1.505
0.247
3.718
0.665
4.049
−4.692
−5.670
−4.972
1.859
0.332
2.024
40.919
10.681
50.042
17.442
3.767
20.130
(A)
(D)
(G)
−5.059
−7.478
−5.475
−4.490
−4.405
−4.966
0.569
3.073
0.509
4.775
5.942
5.221
0.285
1.537
0.255
3.515
0.651
3.929
−4.775
−5.942
−5.221
1.758
0.325
1.965
40.063
11.488
53.543
16.782
3.867
20.513
(A)
(D)
(G)
−4.883
−7.171
−5.015
−4.292
−4.044
−4.494
0.591
3.127
0.521
4.588
5.608
4.755
0.296
1.564
0.261
3.384
0.640
3.839
−4.588
−5.608
−4.755
1.692
0.319
1.919
35.609
10.056
43.388
15.525
3.587
18.251
(A)
(D)
(G)
−6.413
−7.177
−6.087
−4.574
−3.880
−5.314
1.839
3.297
0.773
5.494
5.529
5.701
0.920
1.649
0.387
1.088
0.607
2.587
−5.494
−5.529
−5.701
0.544
0.303
1.294
16.410
9.270
42.038
5.974
3.354
14.750
aSymbols are given in Figure S1.

6 of 16
DIAB ET AL.
lengths and bond angles for tautomeric form (G) of
ligands (HLx) are listed in Tables S1‐S5.
results are found to be in good agreement with the similar
results were obtained recently.[6,41]
The histogram of the HOMO–LUMO energy gap (ΔE)
and the estimated free energy of binding of the receptors
of breast cancer (1JNX) and the prostate cancer (2Q7K)
for the ligands (HLx) is shown in Figure 9. It is observed
that the ΔE values of the ligands (HLx) increases in the
order HL2 < HL3 < HL4 < HL1 < HL5.
3.3 | Molecular docking study of
tautomeric forms (A and D) of ligands
(HLx)
The molecular docking between ligands (HLx) (Figure
S1(A)) and their tautomeric form (D) with two receptors
of the breast cancer (1JNX) and the prostate cancer
(2Q7K) was calculated. The results showed a possible
arrangement between the ligands (HL1–5) (Figure S1(A))
and their tautomeric form (D) with receptors of the breast
cancer (1JNX) and the prostate cancer (2Q7K).[38–40] The
molecular docking study showed a favorable interaction
between the ligands (Figure S1(A)) and their tautomeric
form (D) with 2Q7K and 1JNX receptors (Figures 7,8, S3
and S4) and the calculated energy is listed in Tables 2
and 3. According to the obtained results, HB plot curve
for the receptor of prostate cancer (2Q7K) indicates
that the ligands (HL1,4 and 5) (Figure S1(A)) and tautomeric
form (D) of ligands (HL1–5) bind with hydrogen bond
interactions of the protein and decomposed interaction
energies (kcal/mole) where the HL1–5 ligands (Figure
S1(A)) and their tautomeric form (D) with receptor of
prostate cancer (2Q7K) as appear in Figures S5‐S8. As
well as the interaction for the receptors of prostate
cancer (2Q7K) and breast cancer (1JNX) with the ligands
(HLx) (Figure S1(A)) and their tautomeric form (D) is pos-
sible. 2D plot curves of docking for the ligands (HLx)
(Figure S1(A)) and their tautomeric form (D) with the
receptors of 2Q7K and 1JNX shown in Figures S9‐S12.
These interactions activate apoptosis in cells of cancer for
the interactions with HLx ligands (Figure S1(A)) and their
tautomeric form (D).
3.4 | Infrared spectra and nature of
coordination
The analytical data of the polymer complexes are in good
agreement with stoichiometry proposed for polymer
complexes (see Experimental part). All the polymer
complexes did not melt but decompose at temperature
greater than their ligands, indicating a strong bonding
between the ligands and metal ion. As the reaction
proceeded in the presence of DMF, the ligands dissolved
completely, as shown by the color change of the reaction
mixture.
The polymer complexes were obtained in low yield,
possibly, due to low solubility of the ligands. The values
of the molar conductance in DMF in 10−3 M solutions
are low, suggesting a non‐electrolytic nature for these
polymer complexes. All polymer complexes are stable at
room temperature.
The analytical data of polymer complexes (1–5) are
presented in Experimental part. The polymer complexes
are brightly colored and thermally stable. The polymer
complexes are insoluble in water and common organic
solvents but show solubility in DMSO and DMF. The
analytical data of the polymer complexes indicate 1:2
metal–ligand stoichiometries. The azo dyes have several
coordination sites but the involvement of all donor atoms
in bonding to the metal on formation of a polymer com-
plex is sterically not favorable. However, linear dimers[42]
are possible and the structure of the polymer complexes
may be represented as shown in Figure S1.
The infrared spectra of the metal chelates are complex
and it is not possible to assign all the bands without ambi-
guity. However, structurally important bonds such as
those due to the υ (OH), υ (CO), υ(‐N=N‐) and υ(C=N)
modes are distinguishable and provide inequivalent evi-
The compound has higher value of estimated free
energy of binding against receptor target is strong inhibi-
tory activity. In Tables 2 and 3, the ligands (HLx) (Figure
S1(A)) are efficient inhibitors and the best interaction
with prostate cancer (2Q7K) and breast cancer (1JNX)
than the tautomeric form (D) of ligands (HLx). Also, it
was found that the receptor of prostate cancer (2Q7K)
shows the best interaction than breast cancer (1JNX) with
ligands (HLx) (Figure S1(A)).
dence regarding the structural features of the ligands
2+
The best geometrical structure of the ligands (HL1–5
)
and their manner of bonding with UO2 .
(Figure S1(A)) is agreed well with its predicted best
inhibitory effect to receptors of 2Q7K prostate cancer
and 1JNX breast cancer. In addition to the data proven
that, the HLx ligands (Figure S1(A)) are efficient inhibi-
tors of receptors of prostate cancer and breast cancer
(1JNX) than tautomeric form (D) of ligands (HLx). These
On comparison of the IR spectra data of all the poly-
mer complexes with the data of azo dye ligands, the
absorption modes indicated that the azo dye ligands were
principally coordinated to the uranium metal ion in
tridentate matter. The coordination modes of bonding
have the following remarks:

DIAB ET AL.
7 of 16
FIGURE 6 The optimized molecular structures of the HL5 ligand and its tautomeric forms (D and G)

8 of 16
DIAB ET AL.
FIGURE 7 The ligands (HLx) (green in (a) and gray in (b)) in interaction with receptor of prostate cancer (2Q7K)
2+
1. The presence of UO2 ion in solution exist in a tau-
tomerism equilibrium A ↔ B ↔ C (Figure S1).
2. All polymer complexes {[UO2(Lx)2(OH2)]}n exhibit a
IR broad band at ~ 3325–3345 cm−1, attributed to υ
(OH) of water molecule associated with the forma-
tion of complex as well as new bands in the regions
935–950 and 645–650 cm−1, attributed to ρ(H2O)
and ω(H2O) of the coordinated water molecule
(Figure S13).
υ(C=N) which upon complexation, lying at the
same position, indicating that the N atom of quino-
line ring does not participate in polymer complexes
formation.[43]
5. All the polymer complexes reveal IR bands due to the
υ(‐N=N‐) group which is also observed at lower fre-
quencies at ~ 1570–1560 cm−1 indicating coordina-
tion through one of the nitrogen atom of the azo
group (Figure S13).
3. All the polymer complexes show the disappearance of
the υ (OH) (3210–3325 cm−1) and δ (OH) (1285–
1295 cm−1) and the last band is replaced by a band
at 1295–1315 cm‐1, indicating the coordination
through the oxygen atom (O−) of the phenol group
(C8‐OH) owing to strong hydrogen bonding in both
intramolecular [O‐H … O, O‐H … N] [Figure S1 (B
& C)] and intermolecular hydrogen bonding of the
O‐H …. O type [Figure S1 (E & F)]. This is supported
by the appearance of the characteristic band at 530–
495 cm−1 due to metal‐oxygen stretching vibrations
in the polymer complexes.
6. IR bands at ~ 1655 cm−1 υ (CO) were shifted at
higher frequency in the ligands than in the respec-
tive complexes by 15–25 cm−1, revealing its involve-
2+
ment in UO2 polymer complexes. The decrease
of electronic density of the ring may be correlated
with the donor character of the oxygen atom in
the M‐O bond. A correlation was observed by com-
paring the position of the υ (CO) band in the free
ligand and the corresponding complexes indicating
that the higher electronegativity provides higher
shift.
7. Polymer complexes show a medium intensity band
at 903–940 cm−1 and a strong band at 826–860 cm−1
due to antisymmetric and symmetric frequencies,
4. All the polymer complexes showed a very strong
band at ~1585–1590 cm−1 characterized to pyridine

DIAB ET AL.
9 of 16
FIGURE 8 The ligands (HLx) (green in (a) and gray in (b)) in interaction with receptor of breast cancer (1JNX)
TABLE 2 Energy values obtained in docking calculations of tautomeric forms (A and D)a of ligands (HLx) with receptor of prostate cancer
(PDB code 2Q7K)
Estimated free
energy of
binding
Total
intercooled
Energy
vdW+ bond+
desolv
energy (kcal/mol)
Electrostatic
Energy
(kcal/mol)
Interact
surface
(Å)
Tautomeric
form
Ligand
HL1
(kcal/mol)
(kcal/mol)
(A)
(D)
−6.27
−4.56
−6.59
−5.63
−0.12
−0.11
−6.72
−5.75
561.289
572.803
HL2
HL3
HL4
HL5
(A)
(D)
−7.80
−6.36
−8.29
−7.30
−0.08
−0.07
−8.37
−7.37
544.335
551.696
(A)
(D)
−7.54
−6.16
−8.26
−7.29
−0.07
−0.01
−8.33
−7.29
516.853
514.252
(A)
(D)
−6.73
−5.19
−6.68
−7.71
−0.12
−0.02
−6.79
−7.73
549.458
523.076
(A)
(D)
−4.85
−4.12
−5.87
−7.69
−0.07
+0.06
−5.95
−7.63
552.421
524.546
aSymbols as given in Figure S1.
respectively, indicating that the moieties of UO2+2 are
virtually linear. IR shows bands at 500–518 cm−1 (U‐
O) and 400–417 cm−1 (U‐N) stretching vibrations.
8. IR spectra provide an additional support for the
obtained results from the by considering the changes
for the NMR spectra of the UO22+ polymer complexes

10 of 16
DIAB ET AL.
TABLE 3 Energy values obtained in docking calculations of tautomeric forms (A and D)a of ligands (HLx) with receptor of breast cancer
(PDB code 1JNX)
Estimated free
energy of
binding
vdW+ bond+
desolv
energy
Total
intercooled
Energy
Electrostatic
Energy
(kcal/mol)
Interact
surface
(Å)
Tautomeric
form
Ligand
HL1
(kcal/mol)
(kcal/mol)
(kcal/mol)
(A)
(D)
−4.74
−4.20
−5.93
−5.57
−0.16
−0.02
−6.10
−5.59
599.611
559.121
HL2
HL3
HL4
HL5
(A)
(D)
−5.28
−4.59
−5.83
−5.79
+0.07
−0.01
−5.76
−5.81
599.786
542.572
(A)
(D)
−5.26
−4.48
−5.83
−5.16
+0.06
−0.06
−5.77
−5.22
578.756
537.238
(A)
(D)
−4.86
−4.44
−5.98
−5.61
−0.07
−0.01
−6.05
−5.62
568.751
551.402
(A)
(D)
−4.46
−4.17
−5.72
−5.73
−0.23
+0.10
−5.95
−5.63
604.349
539.02
aSymbols as given in Figure S1.
under investigation in comparison with those of the
free ligands. For polymer complexes, the disappear-
ance of the signal observed at 9.16–12.25 ppm in the
free ligands indicates the involvement and deproton-
ation of the OH group in chelation. Coordinated
water molecules were observed at ~ 3.49 ppm for
polymer complexes.
the polymer complexes show two degradation steps. The
first step beginning at ~ 40 °C is due to the loss of unco-
ordinated water molecules. The second step shows loss of
organic ligand. At temperatures above 500 °C UO3 is
[50,51]
formed then gives U3O8.
TGA studies can be used
to explain the structure of the complexes as well as deter-
mining the nature of the coordinated molecules. From
TGA analyses, it was found that the UO2(II) polymer
complexes (1–4) under investigation are more stable than
the ligand.
9. Various authors[44–49] have also correlated the
basicity of the ligands in the uranyl complexes with
the decrease of antisymmetric stretching frequency
O=U=O (υ3) due to the electrostatic repulsion
between the non‐bonding π‐electrons of the uranyl
oxygen and ligand–metal charge transfer electrons.
3.7 | Kinetic calculations
Coats‐Redfern and Horowitz‐Metzger methods[52,53] were
used for the determination of the thermodynamic param-
eters for polymer complexes (1–4). The enthalpy (ΔH*)
and Gibbs free energy change of the decomposition
(ΔG*) were calculated from the well‐known equations
ΔH* = Ea − RT and ΔG* = ΔH* − TΔS*, respectively, as
well as the thermal activation energy for decomposition
(Ea) and entropy (ΔS*).
Based on the above discussion, the formed polymer com-
plexes coordinate by the oxygen atom of the carbonyl
group, oxygen atom of phenolic group and one nitrogen
atom of the azo dye group are coordinated in a tridentate
binuclear fashion.
3.5 | X‐ray diffraction analysis of the
polymer complexes
The calculated values of Ea, ΔH*, ΔS* and ΔG* of the
decomposition stages for polymer complexes (1–4) are
listed in Table 4 and shown in Figures S15 and S16. The
thermodynamic data obtained from Coats‐Redfern and
Horowitz‐Metzger methods are comparable and can be
considered in good agreement with each other.[25,54]
The entropy is found to be negative values for polymer
complexes (1–4) which indicates more ordered activated
complex than the reactants or the reaction is slow.[32,54]
The entropy reflects the thermal stability of the com-
pounds. The positive value of ΔG* for the polymer
complexes (1–4) indicates that the process is non‐
spontaneous.
The X‐ray powder diffraction of the polymer complexes
(1,3 and 4) are represented in Figure S14. The XRD pat-
terns show the broad peaks in the range 2θ = 18o ‐ 25o
indicating amorphous structures for the polymer
complexes.
3.6 | Thermal studies
The TGA and Dr TGA curves of the polymer complexes
(1–4) are measured from 30 °C to 800 °C with heat flow
15 °C/min and shown in Figure 10. The TGA curves of

DIAB ET AL.
11 of 16
FIGURE 9 The histogram of the
HOMO–LUMO energy gap (ΔE) and the
estimated free energy of binding for the
ligands (HLx) where (a) receptor of
prostate cancer (PDB code 2Q7K) and
(b) receptor of breast cancer (PDB code
1JNX)
and antisymmetric stretching frequencies (υ3) are indica-
tive of the fact that appropriate complexation of the
uranyl ion by ligand groups presumed to lie in, or nearly
in, a plane perpendicular to the axial O‐U‐O direction,
produce extremely large variations in υ1 and υ3 this latter
is evident from the compilation of Table S6. It is also
known that similar large variations in the metal‐oxygen
stretching frequencies of other HLx ligands are occasioned
by change of ligation.[31] It has also observed that the
uranyl stretching frequencies seem to decrease as one
proceeds from left to right along the spectrochemical
series. The antisymmetric stretching frequency (υ3) values
decrease as the donor characteristics increase as is
observed for p‐electron‐releasing substituents, where the
basicity of the donating atom increases. The experimental
results reveals an excellent linear relation between υ1and
3.8 | Determination of the bond lengths of
uranyl ion in polymer complexes
2+
It may be assumed that the uranyl ion UO2 is linear.
Although such linearity may not be deduced completely
unambiguously from any experiment. There is general
accord that a collinear O‐U‐O structure affords the better
interpretation of the Raman infrared and electronic spec-
tra and x‐ray diffraction intensities. It is also rather well
established[31] that the uranyl ion possesses three charac-
teristic IR frequencies: the symmetric stretching fre-
quency, υ1 or σg+, lying in the range 780–900 cm−1; the
asymmetric stretching frequency, υ3 or (σu+, lying in the
range 800–1000 cm−1; and the bending vibration, υ2 or
πu, appearing in the neighborhood of 200 cm−1. The
rather large frequency intervals quoted for symmetric υ1

12 of 16
DIAB ET AL.
FIGURE 10 TGA curves and Dr TGA of polymer complexes
TABLE 4 Thermodynamic activation energy for polymer complexes
Parameter
Decomposition
temperature (°C)
Complexa
(1)
Method
Ea (kJ mol−1
)
ΔS* (J mol−1 K−1
)
ΔH* (kJ mol−1
)
ΔG* (kJ mol−1
)
170–330
CR
HM
CR
50.1
60.7
152
−2.05E+02
−1.79E+02
−7.11E+01
−4.36E+01
45.8
56.3
147
153
150
194
187
330–440
HM
164
158
(2)
(3)
(4)
200–330
330–420
CR
HM
CR
61.7
72
167
180
−1.87E+02
−1.60E+02
−4.49E+01
−1.27E+01
57.2
67.6
162
158
154
191
183
HM
175
190–400
400–530
CR
HM
CR
41.7
44.9
156
−1.91E+02
−2.14E+02
−6.58E+01
−7.09E+01
37.2
40.4
150
140
156
199
215
HM
168
162
150–330
330–410
CR
HM
CR
42.5
50.9
183
−2.20E+02
−1.96E+02
−2.32E+01
1.77E+01
38.2
46.7
178
151
147
193
181
HM
198
193
aNumbers as given in Experimental part.
υ3 with the slope corresponding to (1 + 2MO/MU)1/2 (MO
and MU are the masses of oxygen and uranium atoms,
respectively, (Figure 11a)). Similar results have been
reported by McGlynn and Smith.[55] Instead of the linear
relation between υ1 and υ3 frequencies, the El‐Sonbati
equation[44] has focused attention on their normalized dif-
ferences, in which such differences do not depend on the
masses of oxygen and/or uranium atoms.

DIAB ET AL.
13 of 16
* c
FIGURE 11 The relation between a) υ vs. υ1 and b) υ vs. (υ1 ) for polymer complexes
3
3
It is the purpose of this paper to show how using the
El‐Sonbati equation from which the U‐O bond force con-
stant should eventually serve as a fairly accurate measure
of the U‐O bond distance in given compounds. The force
constant for the U‐O bond [FU‐O10−8 (N/)], (Fs U‐O)t,
(Fs U‐O)o, the U‐O bond distance (rU‐O ()) and spectral
data used herein are summarized in Table S6. It is appar-
ent from Table S6 that a plot of υ1 + υ3 and/or υ3 vs. force
the higher the force constant of the U‐O bond (Figures 14,
S20 and S21). Also, plotting of r1, r2, r3, and rt (bond dis-
tance, rU‐O) vs. υ3 gives straight lines with increase in the
value of υ3 and decrease in rU‐O (Figure S22). Our results
also showed an inverse relationship between υ3 and rU‐O
.
This can be explained by the fact that the electron‐
withdrawing p‐substitution increases the positive charge
2+
on the UO2 leading to an increase in υ3 and FU‐O and
constant for the U‐O [FU‐O 10−8 (N/) or Fx
10−8 (N/)]
subsequently a decrease in rU‐O. Accordingly, rU‐O values
can be arranged in the following order: p‐OCH3 > p‐
CH3 > H > p‐Cl > p‐NO2, was achieved in consistent
with the positive charge on the UO22+. The plot of
U‐O
and the U‐O bond distance (rU‐O () or rU‐O ()) gives a
straight line with an increase in the value of υ1 + υ3
and/or υ3 decrease rU‐O and an increase in the force con-
stant of the U‐O bond as shown in Figures 12,13 and S17‐
S19. There is also a straight line relationship between rU‐O
R
Hammett's substituent coefficients (σ ) vs. a) r1 (Å) and
b) FU‐O (10−8 (N/Å)) of UO2 complexes (1–5) (Fig-
2+
R
and p‐subsistent, Hammett's constant (σ ) with negative
ures 14, S20 and S21) shows all these FU‐O values increase
R
slop, i.e., the higher the value of the R, the lower rU‐O and
with increasing σ
while r1 values decrease with
FIGURE 12 The relation r3 (Å) and
FU‐O (10−8 (N/Å)) with υ3 (cm−1) for
polymer complexes

14 of 16
DIAB ET AL.
FIGURE 13 The relation r3 (Å) and
Fx (10−8 (N/Å)) with υ3 (cm−1) for
U‐O
polymer complexes
FIGURE 14 The relation between
Hammett's substituent coefficients (σR) vs.
a) r1 (Å) and b) FU‐O (10−8 (N/Å)) of
polymer complexes
increasing σR, this can be attributed to the fact that the
charge effectively increased due to the electron withdraw-
ing substituent in complexes (4 & 5), while it decreased
by electrons donating character of complexes (1 & 2).
This is in accordance with that expected from Hammett's
constant (σ R). These data can be explained by El‐Sonbati
equation[44] for calculating the symmetric stretching fre-
their normalized differences. Thus a new relationship
between them with respect to rt was determined by
Clobal error which shows that the excellent validity is
in the sequence: √(r3‐rt)2 (0.0062)
>
√(r1‐rt)2
(0.0353) > √(r2‐rt)2 (0.0906) for the force constant FU‐O
and bond length, r of the uranyl polymer complexes.
U‐O
Due to small scattering power of the oxygen atom, report
of the determination of U–O bond length of some uranyl
complexes by X‐ray study is inadequate. From the IR
spectra, the stretching and interaction force constants of
the complexes have been calculated.[31,45–49] The data
were used to evaluate the U‐O bond distances using Bad-
ger's formula, Jones equation[47,48] and El‐Sonbati
x
x
quency (υ1 ). The (υ1 ) data served as an accurate evalua-
tion to the (FU‐O) and (rU‐O). There is also a straight line
x
relationship between (υ1 ) and (υ3) (O=U=O) (Figure 11
b). Perhaps a new light can be shed on the problem by
looking at the values of r1, r2 and r3 from a different point
of view. It might be worthwhile to focus attention on

DIAB ET AL.
15 of 16
equation.[44] The data are quite close to the results
reported earlier for other uranyl complexes.[44,49] The var-
iation of bond length in the complexes is due to the pres-
ence of electron releasing or electron withdrawing
substituents in the equatorial position.
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4 | CONCLUSION
[7] K. B. Patel, G. J. Kharadi, K. S. Nimavat, J. Chem. Pharm. Res.
2012, 4, 2422.
The {[UO2(Lx)(OH2)]}n polymer complexes (1–5) of azo
dye ligands 5(4`‐derivatives phenylazo)‐8‐hydroxy‐7‐
quinolinecarboxaldehyde (HLx) were prepared and char-
acterized by elemental analysis, 1H NMR, IR spectra,
thermal analysis and X‐ray diffraction analysis. Based
on the above discussion, the ligands (HLx) are monobasic
and the formed polymer complexes coordinate by the
oxygen atom of the carbonyl group, oxygen atom of phe-
nolic group and one nitrogen atom of the azo dye group
are coordinated in a tridentate binuclear fashion. Molecu-
lar docking of the binging between the form (A) of HLx
and their tautomeric form (D) with two receptors of the
breast cancer (1JNX) and the prostate cancer (2Q7K)
was discussed. It was found that the receptor of prostate
cancer (2Q7K) shows the best interaction than breast can-
cer (1JNX) with ligands (HLx) than tautomeric form (D)
of ligands (HLx). Also, it was found that the best geomet-
rical structure of the ligands (HLx) agreed well with its
predicted best inhibitory effect to receptors of prostate
cancer and breast cancer. It was found that the FU‐O
values increase with increasing σR while r1 values
decrease with increasing σR. In case FU‐O values increase
with increasing Hammett's substituent coefficients (σR),
this can be attributed to the fact that the charge effec-
tively increased due to the electron withdrawing substitu-
ent in UO2(II) polymer complexes (4) and (5), while it
decreased by electrons donating character of UO2(II)
polymer complexes (1) and (2). This is in accordance
with that expected from Hammett's constant (σR).
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Sh. M. Morgan, O. L. Salem, A. M. Eldesoky, Mater. Sci. Eng.
C 2019, 103, 109727.
[11] M. Albrecht, K. Witt, R. Frohlich, O. Kataeva, Tetrahedron
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[12] K. D. Patel, H. S. Patel, Pharm. Lett. 2011, 3, 356.
[13] D. A. Pearce, N. Jotterand, I. S. Carrico, B. Imperiali, J. Am.
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[19] A. Z. El‐Sonbati, M. A. Diab, A. A. M. Belal, Sh. M. Morgan,
Spectrochim. Acta A 2012, 99, 353.
[20] N. A. El‐Ghamaz, M. A. Diab, A. Z. El‐Sonbati, O. L. Salem,
Spectrochim. Acta A 2011, 83, 61.
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O. L. Salem, Chem. Pap. 2017, 71, 2417.
[22] A. Z. El‐Sonbati, A. A. M. Belal, M. S. El‐Gharib, Sh. M. Mor-
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ORCID
[23] N. A. El‐Ghamaz, A. Z. El‐Sonbati, Sh. M. Morgan, J. Mol.
Struct. 2012, 1027, 92.
M.A. Diab https://orcid.org/0000-0002-9042-1356
A.Z. El‐Sonbati https://orcid.org/0000-0001-7059-966X
Sh.M. Morgan https://orcid.org/0000-0002-8921-4894
[24] M. I. Abou‐Dobara, A. Z. El‐Sonbati, Sh. M. Morgan, World J.
Microbiol. Biotechnol. 2013, 29, 119.
[25] Sh. M. Morgan, A. Z. El‐Sonbati, M. A. El‐Mogazy, Appl.
Organomet. Chem. 2018, 32, e4264.
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SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of the
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How to cite this article: Diab MA, Nozha SG, El‐
Sonbati AZ, El‐Mogazy MA, Morgan ShM. Polymer
complexes. LXXVIII. Synthesis and
characterization of supramolecular uranyl polymer
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