Binuclear and polymeric Hg(II) complexes of an ambidentate phosphorus ylide: Synthesis, crystal structure, antibacterial activity, and theoretical studies

Article abstract of DOI:10.1002/aoc.5265

The new α-keto-stabilized phosphorus ylide Ph₃PCHC(O)PhCN (Y) was synthesized by addition of triphenylphosphine to 2-bromo-4′-cyanoacetophenone, followed by treatment with NaOH 10%. Reaction of ligand (Y) with methanolic solution of mercury(II)

Full text of DOI:10.1002/aoc.5265

Received: 6 June 2019
DOI: 10.1002/aoc.5265
Revised: 15 August 2019
Accepted: 7 September 2019
F U L L P A P E R
Binuclear and polymeric Hg(II) complexes of an
ambidentate phosphorus ylide: Synthesis, crystal structure,
antibacterial activity, and theoretical studies
Seyyed Javad Sabounchei1
| Faeze Kazemi Andalib1 | Marjan Hosseinzadeh1 |
Asieh Sedghi1 | Ali Hashemi1 | Roya Karamian2 | Kristof Van Hecke3
1 Faculty of Chemistry, Bu‐Ali Sina
University, Hamedan 65174, Iran
The new α‐keto‐stabilized phosphorus ylide Ph3PCHC(O)PhCN (Y) was syn-
2 Department of Biology, Faculty of
Science, Bu‐Ali Sina University, Hamedan
65174, Iran
3 XStruct, Department of Chemistry,
Ghent University, Krijgslaan 281‐S3, B‐
9000 Ghent, Belgium
thesized by addition of triphenylphosphine to 2‐bromo‐4′‐cyanoacetophenone,
followed by treatment with NaOH 10%. Reaction of ligand (Y) with methanolic
solution of mercury(II) halides under mild conditions yielded the binuclear
complexes [Y·HgX2]2 [X=Cl (1), Br (2), I (3)]. The new organic/inorganic com-
posite polymer [Hg(NO3)2(Y)]n (4) was synthesized by the reaction of mercury
(II) nitrate with the phosphorus ylide Y. Compounds synthesized were charac-
Correspondence
terized by Fourier‐transform infrared, H, 31P, and 13C nuclear magnetic reso-
1
Seyyed Javad Sabounchei, Faculty of
Chemistry, Bu‐Ali Sina University,
Hamedan, 65174, Iran.
nance spectroscopic methods, which confirmed the coordination of ylide to
the metal center through the ylidic carbon atom. Single‐crystal X‐ray structures
of phosphorus ylide Y and polymeric complex 4 were also determined and the
crystallographic data of complex 4 showed that the title complex has an infinite
one‐dimensional structure. Furthermore, the electronic and molecular struc-
tures of complexes 1–3 were investigated at the BP86/def2‐SVP level of theory,
Email: jsabounchei@yahoo.co.uk
indicating an increasing trend for C→M bond lengths: Hg2I2 > Hg2Br2
>
Hg2Cl2 in [Y→HgX2]2 (X = Cl, Br, I) complexes. In addition, the antibacterial
activity of ligand Y and all complexes using the agar disc diffusion method
was examined against both selected gram‐positive and gram‐negative bacteria.
Results indicated that the ligand Y and complexes 1 and 4 show good antibac-
terial effect against gram‐positive bacteria tested; besides, the inhibition zones
of complexes were significantly larger than those of chloramphenicol as
standard.
KEYWORDS
antibacterial activity, crystal structure, phosphorus ylide, spectroscopic characterization, theoretical
studies
1 | INTRODUCTION
properties.[1–4] Phosphorus ylides, a special class of zwit-
terions, carry strongly nucleophilic electron‐rich carban-
Organophosphorus compounds are important in syn-
thetic organic chemistry, particularly in the synthesis of
compounds with biological and pharmacological
ions. The electron distribution around the P+–C– bond
and its resulting chemical implications have been
explored and assessed through theoretical, spectroscopic,
Appl Organometal Chem. 2019;e5265.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5265

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SABOUNCHEI ET AL.
and crystallographic investigation. In recent years, multi-
ple reports for the synthesis of new phosphorus ylides
have been published which renders their study an out-
standing conquest in the chemistry of the twentieth cen-
tury.[5] They are usually prepared by the treatment of a
phosphonium salt with a base. The corresponding phos-
phonium salts can be synthesized by Michael addition
of phosphorus nucleophiles to the activated alkyl/aryl
halides.[2,3,6] The chemistry of metal complexes with
ylides is a subject of present interest.[7] The α‐stabilized
phosphorus ylides [Ph3P=C(H)R] [R=CN, C(O)R′; R′ =
Me, Ph, OMe, NMe2] have proven to be versatile ligands
toward transition metals because of the presence of differ-
ent functional groups in their molecular structure.[7–11]
This versatility has allowed the formation of coordinated
ylides in different binding modes: C coordinated (via the
Cα atom), O bonded (via the carbonyl O), N‐bonded (via
the N of the cyano group), or even situations in which
the same ylide shows a combination of binding modes.[7]
Synthesis of complexes derived from phosphorus ylides
and Hg(II) salts was started in 1965 by Nesmeyanov
et al.[12] In 1975, Weleski et al.[13] proposed a symmetric
halide‐bridged dimeric structure for Hg(II) halide com-
plexes, whereas Kalyanasundari et al.[14] reported an
asymmetric halide‐bridged dimeric structure in 1995. In
1985, Sanehi et al.[15] reported a mononuclear Hg(II)
complex of phosphorus ylides without any structural
characterization. The α‐keto‐stabilized phosphorus ylides
R3PC(R′)COR″ show interesting properties such as high
stability and ambidentate character as ligands (C vs. O
coordination).[16–19] We have recently focused on the syn-
thesis of binuclear and polynuclear complexes using mer-
cury(II) salts and phosphorus ylides and investigation of
their spectroscopic and crystal structures.[20–22] New
developments in the crystal chemistry of metal–organic
coordination polymers have introduced many novel
materials with various structural features and properties.
Supramolecular structures with mercury(II) atoms seem
to have much similarity with low‐valent main group ele-
ments than the transition metals, because they form
structures with low‐coordinate linear or other distorted
coordination geometries.[23]
materials have several benefits over commonly used
organic compounds, including chemical stability, ther-
mal resistance, safety to the user, long lasting action
period, etc.[26]
Herein, we report the self‐assembly and resulting
structures of a new phosphorus ylide and four mercury
(II) complexes of different compositions, [HgX2Y]2 and
[Hg(NO3)2Y]n [X = Cl, Br, and I; Y= Ph3PCHC(O)PhCN].
These compounds have been characterized by Fourier‐
transform infrared (FT‐IR), 1H nuclear magnetic reso-
nance (NMR), 31P NMR, and 13C NMR spectroscopic
studies, and for phosphorus ylide Y and the [Hg(NO3)
2Y]n complex, additionally, by single‐crystal X‐ray analy-
sis. Throughout this research, the antibacterial activity
of the synthesized ylide and complexes has been studied
by the disc diffusion method against specific gram‐
positive and gram‐negative bacteria.[27]
2 | EXPERIMENTAL
2.1 | General considerations
Solvents were reagent grade and starting materials were
purchased from commercial sources and used without
further purification. Melting points were measured on
an SMPI apparatus. IR spectra were recorded on a Perkin
1
Elmer G X FT‐IR spectrometer from KBr pellets. H, 13C
{1H}, and 31P{1H} NMR spectra were recorded on a 250‐/
400‐MHz Bruker and a 90‐MHz JEOL spectrometer using
deuterated dimethyl sulfoxide (DMSO‐d6) or CDCl3 as
solvents at 25 °C. Chemical shifts (ppm) were reported
according to the internal standard tetramethylsilane (1H,
13C) and external standard 85% phosphoric acid (31P).
Coupling constants were given in Hertz. Suitable crystals
were obtained by slow evaporation of methanol as the sol-
vent and vapor diffusion of diethyl ether into acetonitrile
and mounted in random orientation or mounted on a
nylon loop.
2.2 | X‐ray crystallography
Antibacterial agents are often co‐administered with
an inhibitor that breaks down the bacterial resistance
mechanism and increases the effectiveness of the inhib-
itor agents[24] The development of compounds with the
ability to inhibit bacterial growth has been of great
interest in recent years due to the increase of bacterial
resistance against present antibiotics and antibacterial
compounds[25] Antibacterial agents have potential to be
used both in hospital equipment and in everyday items
such as soaps, detergents, health, and skincare products
and household cleaners[24] Inorganic antibacterial
Colorless crystals of the synthesized phosphorus ylide Y
and mercury(II) nitrate complex 4 were crystallized by
vapor diffusion of diethyl ether into chloroform. A suit-
able crystal was selected and mounted on a nylon loop
on a SuperNova, Dual, Cu at zero, Atlas diffractometer.
Using Olex2,[28] the structure was solved with
SHELXS.[29] Data were collected for Y at 293(2) K with
structure solution program using direct methods. For
complex 4 the crystal was kept at 100.0(1) K during data
collection, which was performed with structure solution
program using intrinsic phasing. Both data were refined

SABOUNCHEI ET AL.
3 of 13
with the SHELXL[30] refinement package using least‐
squares minimization on F 2 using all data. All non‐
hydrogen atoms were refined with anisotropic displace-
ment parameters, whereas all hydrogen atoms were
placed at geometrical estimates and refined using the rid-
ing model with an isotropic displacement parameter
equal to 1.2 times Ueq of the parent atom. Both structures
showed residual electron density peaks around the metal
atoms due to minor disorder, 0.27 and –0.30 e Å–3 for Y,
and 1.82 and –1.28 e Å–3 for 4; attempts to model this dis-
order were not successful.
for 12 hr. The resulting white precipitate was filtered
off, washed with petroleum benzine, and dried. Further
treatment with an aqueous solution of NaOH (0.5 M, 10
ml) led to the elimination of HBr, affording the free
ligand (Y). The resulting white precipitate was filtered
off, washed with petroleum benzine, and dried
(Scheme 1).[22,31–33]
2.3.1 | Data for Ph3PCHC(O)PhCN (Y)
Yield: 0.37 g (92%), melting point, 115–117 °C. IR (KBr
disk, cm–1) υ: 1572 (C=O), 883 (P–C) (Figure S1). 1H
NMR (CDCl3) δH: 4.40 (br, 1H, CH); 7.25–8.03 (m, 19H,
Ph) (Figure S2). 31P NMR (CDCl3): δP = 16.84 (s, PPh3)
2.3 | Synthesis of Ph3PCHC(O)PhCN (Y)
1
A solution consisting of triphenyl phosphine (0.26 g, 1
mmol) and 2‐bromo‐4‐cyanoacetophenone (0.22 g, 1
mmol) in dried acetone (25 ml) was stirred at 40 °C
(Figure S3). 13C NMR (CDCl3): δC = 52.10 (d, CH, JPC
= 111.33); 112.43 (s, CN); 119.14–133.40 (m, Ph); 182.30
(s, CO) (Figure S4).
SCHEME 1 Synthesis of the ylide Y and its complexes (1), (2), (3), and (4). r.t., room temperature

4 of 13
SABOUNCHEI ET AL.
hr and products were filtered, washed with petroleum
benzine, and dried (Scheme 1).[37–39]
2.4 | Synthesis of Hg(II) halide dimeric
complexes
2.4.1 | General procedure
2.5.1 | Data for [Ph3PCHC(O)PhCN·Hg
(NO3)2]n (4)
To HgX2 (1 mmol of 0.26 g HgCl2 or 0.35 g HgBr2 or 0.45
HgI2) dissolved in 10 ml of dried methanol, the ylide (0.40
g, 1 mmol) was added at room temperature. The mixture
was stirred for approximately 8 hr and products were fil-
tered, washed with petroleum benzine, and dried
(Scheme 1).[34–36]
Yield: 0.69 g (87%), decomp. at 217 °C. IR (KBr, cm–1) υ:
1659 (C=O), 815 (P–C) (Figure S17). H NMR (DMSO‐
d6) δH: 6.49 (br, 1H, CH); 7.48–8.29 (m, 19H, Ph) (Figure
S18). 31P NMR (DMSO‐d6): δP = 27.64 (s, PPh3) (Figure
S19). 13C NMR (DMSO‐d6): δC = 116.36 (s, CN); 118.29–
139.00 (m, Ph); 192.84 (s, 2C, CO) (Figure S20).
1
2.4.2 | Data for [Ph3PCHC(O)PhCN·HgCl2]
(1)
2
2.6 | Computational studies
Yield: 0.84 g (65%), decomp. at 192–195 °C. IR (KBr disk,
1
cm–1) υ: 1630 (C=O), 807 (P–C) (Figure S5). H NMR
The geometries of the synthesized mercury(II) halide
complexes [{Ph3PCHCOC6H4‐p‐CN}→HgX2]2 (X = Cl,
Br, I) were optimized without symmetry constraints at
the BP86[40]/def2‐SVP[41] level of theory using the Gauss-
ian 09[42] optimizer. Recent studies have shown that BP86
is a suitable method for the calculation of L→M bond
properties in ylidic complexes.[43,44] A natural bond
orbital (NBO) analysis was also carried out with the inter-
nal model Gaussian 09 program[45,46] The observed geom-
(DMSO‐d6) δH: 5.26 (br, 2H, CH); 7.19–8.15 (m, 38H,
Ph) (Figure S6).31P NMR (DMSO‐d6): δP = 21.01 (s,
PPh3) (Figure S7). 13C NMR (DMSO‐d6): δC = 49.07 (d,
1
CH, JPC = 84.52); 112.09 (s, CN); 118.66–133.17 (m,
Ph); 185.55 (s, CO) (Figure S8).
2.4.3 | Data for [Ph3PCHC(O)
PhCN·HgBr2]2 (2)
etry
of
the
already
synthesized
compound,
[{Ph3PCHCOC10H7}→HgX2]2 (X = Cl, Br, I), was used
as a basis for the density functional theory (DFT) calcula-
tions.[47] The bonding analyses, in terms of energy‐
decomposition analysis (EDA), were conducted at the
BP86/TZ2P(ZORA)//BP86/def2‐SVP level of theory with
C1 symmetry. The basis sets for all elements have triple‐
f quality augmented by one set of polarization functions
[ADF basis set TZ2P(ZORA)] with the program package
ADF2013.01. EDA calculations were carried out to ana-
lyze the nature of the C(carbene)→M bond.[48–50]
Yield: 0.88 g (58%), decomp. at 214–217 °C. IR (KBr disk,
cm1) υ: 1641 (C=O), 816 (P–C) (Figure S9). 1H NMR
2
(DMSO‐d6) δH: 5.09 (d, JPH=12.50 Hz, 2H, CH); 7.59–
8.11 (m, 38H, Ph) (Figure S10). 31P NMR (DMSO‐d6): δP
= 20.03 (s, PPh3) (Figure S11). 13C NMR (DMSO‐d6): δC
1
= 49.17 (d, CH, JPC = 94.35); 113.14 (s, CN); 119.16–
143.61 (m, Ph); 185.02 (s, CO) (Figure S12).
2.4.4 | Data for [Ph3PCHC(O)PhCN·HgI2]2
(3)
2.7 | Antibacterial assay
Yield: 1.17 g (69%), decomp. at 214–217 °C. IR (KBr disk,
1
cm–1) υ: 1637 (C=O), 801 (P–C) (Figure S13). H NMR
The potential antibacterial effects of the synthesized
phosphorus ylide Y and mercury(II) complexes 1–4 were
investigated by the disc diffusion method against five
gram‐positive bacteria, namely, Bacillus cereus (American
Type Culture Collection [ATCC] 7064), Staphylococcus
saprophyticus (ATCC 15305), Bacillus subtilis (ATCC
6633), Staphylococcus aureus (ATCC 6538), and Bacillus
thuringiensis (Lio), and against four gram‐negative bacte-
ria, namely, Escherichia coli (plant tissue and cell culture
[PTCC] 10009), Pseudomonas fluorescens (PTCC 1181),
Pseudomonas aeruginosa (ATCC 25923), and Klebsiella
oxytoca (Lio).[51] The organisms were sub‐cultured in
nutrient broth and nutrient agar (Oxoid Ltd.) for
1
(DMSO‐d6) δH: 4.94 (d, 2H, CH, JPC = 20.00); 7.68–8.19
(m, 38H, Ph) (Figure S14). 31P NMR (DMSO‐d6): δd =
17.65 (s, PPh3) (Figure S15). 13C NMR (DMSO‐d6): dC =
1
50.12 (d, CH, JPC = 103.63); 113.65 (s, CN); 119.03–
144.12 (m, Ph); 186.93 (s, CO) (Figure S16).
2.5 | Synthesis of the Hg(II) nitrate
complex
To Hg(NO3)2·H2O (0.36 g, 1 mmol) dissolved in 10 ml of
dried methanol, the ylide (0.40 g, 1 mmol) was added at
room temperature. The mixture was stirred for about 8

SABOUNCHEI ET AL.
5 of 13
experimental use, while agar (Diagnostic Sensitivity Test
Agar or D.S.T.A.; Oxoid Ltd.) was used in antibiotic sensi-
tivity testing.
The complexes and ligand were dissolved in DMSO to a
final concentration of 1 mg ml–1 and then sterilized by fil-
tration using a 0.2‐μm filter (Millipore). All tests were car-
ried using 10 ml of suspension containing 1.5 × 108 bacteria
ml–1 and spread on nutrient agar medium. The test samples
were dissolved in DMSO at a concentration of 1 mg ml–1.
The sensitivity testing was performed using the agar‐gel
diffusion method.[24,52] In each disk, 20 μl of each chemi-
cal, containing 10 μg in DMSO, was loaded. Because DMSO
was used as a solvent, it was also screened against all bacte-
rial species used in this study as a negative control. Chlor-
amphenicol was used as a positive reference standard.
The diameters of inhibition zones generated by the com-
plexes were measured.
3 | RESULTS AND DISCUSSION
3.1 | Synthesis
The phosphorus ylide Y was synthesized by reaction of 2‐
bromo‐4′‐cyanoacetophenone with triphenylphosphine
and concomitant treatment with NaOH. The mercury com-
plexes were prepared through the reaction of Y as a new
phosphorus ylide ligand, Ph3PCHC(O)PhCN, and a mer-
cury salt, resulting in the formation of complexes with
the general stoichiometry [HgX2Y]2, where X is chloride,
bromide, or iodide. The one‐dimensional polymer [Hg
(NO3)2(Y)]n (4) was also synthesized by the reaction of Y
and Hg(NO3)2·H2O in methanol. In fact, one equivalent
of HgX2 or Hg(NO3)2·H2O reacts with one equivalent of Y
to give a precipitate which proved to consist of mercury
complexes and one‐dimensional mercury polymer, respec-
tively. The synthesized polymeric [Hg(NO3)2Y]n complex
can be recrystallized using a large volume of acetonitrile
to provide crystals suitable for X‐ray diffraction analysis.
The results of the crystal structure determinations of Y
and 4 are consistent with the chemical and spectroscopic
analyses, providing clear evidence of the formation of the
phosphorus ylide and the corresponding [Hg(NO3)2Y]n
complex.
FIGURE 1 (a) X‐ray crystal structure of ylide Y, Ph3PCHC(O)
PhCN, and (b) complex 4, [Ph3PCHC(O)PhCN·Hg(NO3)2]n
asymmetric unit
The X‐ray structure of stabilized phosphorus ylide Y
is shown in Figure 1a. Ylidic resonance is important in
Y stabilized by electron‐withdrawing substituents due
to electronic delocalization between the P–C bond, the
ylidic bond, and an acyl group.[53,54] There is a slightly
distorted tetrahedral arrangement around the P atom,
as observed for stabilized keto–ester phosphorus
ylides.[55] The P–C bonds [P1–C1 = 1.729(2), P1–C10 =
1.813(3), P1–C16 = 1.809(2) and P1–C22 = 1.809(2) Å]
[55]
[56]
comparable to analogous distances in
and
are
longer than the typical double P–C bond in
methylenetriphenylphosphorane and Ph3PCH2. The X‐
ray crystal structure analysis shows that complex 4
adopts a non‐centrosymmetric polymeric structure with
NO3 bridge. As illustrated in Figure 1, the Hg atom in
each unit surrounded by six oxygen comes from NO3
groups and ylidic carbon with the Hg–C distance of
2.120(6) Å and two oxygen atoms of the nitrate ligand
3.2 | X‐ray crystallography
The molecular structures of the synthesized phosphorus
ylide Y and mercury(II) nitrate complex 4 are shown in
Figure 1 and the relevant parameters concerning data col-
lection and refinement are summarized in Table 1.
Selected bond distances and bond angles for the unit cells
of Y and 4 are presented in Tables 2 and 3.

6 of 13
SABOUNCHEI ET AL.
TABLE 1 Crystallographic data summary for ylide Y and complex 4
Compound
Ylide Y
Complex 4
Empirical formula
C27H20NOP
C29H23HgN4O7P
Formula weight
Temperature (K)
Crystal system
Space group
a (Å)
405.41
771.07
293(2)
100.0(1)
Monoclinic
Orthorhombic
P21/n
P212121
13.2796(2)
10.3387(2)
b (Å)
11.29431(19)
16.1945(4)
c (Å)
14.9318(2)
17.4654(3)
α (°)
90
90
β (°)
106.1325(18)
90
γ (°)
90
90
Volume (Å3)
2151.34(6)
2924.23(10)
Z
4
4
ϱcalc (g cm–3
)
1.252
1.751
μ (mm–1
)
1.264
5.371
F(000)
848.0
1504.0
Crystal size (mm3)
0.25 × 0.191 × 0.127
Cu‐Kα (λ = 1.54184)
7.892 to 150.672
0.327 × 0.192 × 0.144
Mo‐Kα (λ = 0.71073)
5.03 to 59.382
Radiation
2θ range for data collection (°)
Index ranges
–16 ≤ h ≤ 16, –11 ≤ k ≤ 13, –18 ≤ l ≤ 17
20,646
–13 ≤ h ≤ 13, –22 ≤ k ≤ 20, –24 ≤ l ≤ 21
Reflections collected
18,773
Independent reflections
Data/restraints/parameters
Goodness‐of‐fit on F 2
Final R indexes [I ≥ 2σ (I)]
Final R indexes [all data]
Largest diffraction peak/hole (e Å–3
Flack parameter
4315 [Rint = 0.0577, Rsigma = 0.0477]
4315/0/271
7118 [Rint = 0.0592, Rsigma = 0.0814]
7118/0/381
1.020
1.026
R1 = 0.0575, wR2 = 0.1411
R1 = 0.0842, wR2 = 0.1624
0.27/–0.30
R1 = 0.0438, wR2 = 0.0669
R1 = 0.0605, wR2 = 0.0753
1.82/–1.28
)
0.491(9)
3.3 | Spectroscopy
3.3.1 | Infrared spectra
with Hg–O distances of 2.159(6) and 2.512(7)
Å
(Table 3). The coordination number in this complex is
seven (one of ylide, two of one bidentate nitrate anion,
and four of two bridged nitrates). There are only a few
inorganic examples of bridging nitrates with different
coordination modes: bidentate,[57] tridentate,[58] and
tetradentate[59] but in 4 there are two different nitrate
anions: one of them acts as bidentate and the other
one acts as both bidentate and bridging groups (totally
tetradentate). The C2–O1 distance in complex 4 is
shorter than the aforementioned ylide, showing the C
coordination of ylide to the metal center. By contrast,
the P1–C1 distance in complex 4 is longer than ylide,
showing the elimination of electron delocalization in
P–C1–C2=O by coordination of C1 to the Hg center.
In the IR spectra of the phosphorus ylide Y, a strong
stretching absorption due to the carbonyl group was
observed at 1572 cm–1.[60,61] Coordination of the ylide
through the carbon atom causes an increase in νCO,
whereas for O coordination a lowering of νCO is expected.
Because of the coordination of Y to mercury(II) atoms,
the resonance between C=O and C=P is destroyed and
C=O becomes weaker. As a result, the infrared spectra
of the complexes in the solid state show a νCO in the
range of 1630–1659 cm–1 at higher frequencies with
respect to the free ylide. The νPC frequency, which is also

SABOUNCHEI ET AL.
7 of 13
diagnostic of the coordination, occurs at 883 cm–1 for Y.
In this study, the νPC values for all complexes were
shifted to lower frequencies, because P=C is stronger
and is observed in the range of 801–816 cm–1.[60,62]
According to the spectra, the interaction in the binuclear
complexes is weaker than in the polymeric structure
(Table 4).
TABLE 2 Selected key bond lengths (Å) and angles (°) for com-
plex 4
Bond lengths
Hg1–O2
Length (Å)
2.159(6)
2.512(7)
2.120(8)
1.800(8)
1.806(9)
1.797(9)
1.803(9)
1.495(4)
1.229(3)
Angle (°)
80.7(2)
Hg1–O5
Hg1–C1
P1–C1
P1–C10
3.3.2 | NMR spectral data
P1–C16
1
In the H NMR spectra, methinic protons exhibit doublet
P1–C22
or broad doublet signals. This broadening might be a
result of coupling to 199Hg and forming satellites.[63] The
expected downfield shifts of 1H signals for the PCH group
upon complexation in the case of C coordination were
observed in their corresponding spectra (Table 4).[64]
The 31P NMR spectra of all the compounds show all
the expected resonances for the proposed structures. The
31P NMR spectrum of phosphorus ylide Y shows a singlet
at 16.83 ppm, which corresponds to the PPh3 group. The
phosphorus atom of this compound shows an upfield shift
compared with that of the parent phosphonium salt, sug-
gesting some electron density increase in the P–C
bonds.[46,60] At room temperature, 31P NMR spectra of
complexes 1–4 exhibit a singlet around 17 to 27 ppm,
which can be assigned to the PPh3 group. This chemical
shift is at a lower field than the one observed for the cor-
responding free ylide (around 16 ppm), indicating that the
coordination of the ylide has occurred (Table 4).
C1–C2
O1–C2
Bond angles
O2–Hg1–O5
C1–Hg1–O2
C1–Hg1–O5
N2–O2–Hg1
N3–O5–Hg1
P1–C1–Hg1
C2–C1–Hg1
173.1(3)
105.0(3)
106.8(5)
109.4(6)
112.3(4)
111.0(5)
TABLE 3 Selected key bond lengths (Å) and angles (°) for ylide Y
Bond lengths
P1–C1
Length (Å)
1.729(2)
The most interesting aspect of the 13C NMR spectra of
the complexes is the upfield shift of the signals due to the
ylidic carbon. Such an upfield shift of δ 3–10 ppm with
P1–C10
1.813(3)
P1–C16
1.809(2)
reference to the parent ylide was also observed in the case
P1–C22
1.809(2)
[65]
of [Ph3PCHC(O)PhCN·HgI2]2
and our previously syn-
O1–C2
1.252(3)
thesized complexes.[66] The 13C shifts of the CO group in
the complexes are around 190 ppm, relative to 182 ppm
noted for the same carbon in the parent ylide, confirming
the correct synthesis of these complexes.
C1–C2
1.390(3)
Bond angles
C1–P1–C10
C1–P1–C16
C1–P1–C22
C16–P1–C10
C16–P1–C22
C22–P1–C10
C2–C1–P1
C11–C10–P1
C15–C10–P1
C17–C16–P1
C21–C16–P1
C23–C22–P1
C27–C22–P1
Angle (°)
114.35(11)
113.27(11)
107.55(11)
109.09(11)
106.05(11)
105.93(11)
118.73(18)
119.47(18)
120.97(19)
122.2(2)
3.4 | Theoretical studies
The structures of synthesized mercury(II) halide com-
plexes [{Ph3PCHCOC6H4‐p‐CN}→HgX2]2 [X = Cl (1), Br
(2), I (3)] complexes are optimized at the BP86/def2‐SVP
level of theory. These optimized structures and the trends
for the variation of the corresponding bond lengths and
bond angles are shown in Figure 2. As can be seen in
Figure 2, there is an increasing trend for C→M bond
lengths when the Hg2X2 fragment changes from Hg2Cl2
118.17(19)
121.79(19)
119.27(19)
to Hg2I2 as Hg2I2
>
Hg2Br2
>
Hg2Cl2 for
[{Ph3PCHCOC6H4‐p‐CN}→HgX2]2 [X = Cl (1), Br (2), I
(3)] complexes.

8 of 13
SABOUNCHEI ET AL.
1
TABLE 4 FT‐IR, 13C, and H and 31P NMR data of the ylide and its synthesized complexes
FT‐IR
1H NMR
31P NMR
13C NMR
Compounds
νCO
νPC
δCH
J(P–H)
δPCH
δCO
δCH
J(P–CH)
Ya
1b
2b
3b
4b
1572
883
4.40(br)
–
16.84(s)
182.30(s)
52.10(d)
111.33
1630
1641
1637
1659
807
816
801
815
5.26(br)
5.09(d)
4.94(d)
6.49(br)
–
21.01(s)
20.03(s)
17.65(s)
27.64(s)
185.55(s)
185.02(s)
186.93(s)
192.84(s)
49.07(d)
49.17(d)
50.12(d)
–
84.52
94.35
103.63
–
12.50
20.00
–
FT‐IR, Fourier‐transform infrared; NMR, nuclear magnetic resonance; s, Singlet; d, doublet; br, broad.
aRecord in CDCl3.
bRecorded in deuterated dimethyl sulfoxide (DMSO‐d6).
FIGURE 2 Optimized structures of [{Ph3PCHCOC5H4CN}2→HgX2]2 (X = Cl, Br, I) complexes at the BP86/def2‐SVP level of theory. Bond
lengths are given in Angstrom, bond angles in degrees
This trend is predictable due to the change in halogen
electronegativity and the halogen atomic radius.
the optimized structures [{Ph3PCHCOC6H4CN}→HgX2]2
[X = Cl (1), Br (2), I (3)].
In this regard, the largest (2.43 Å) and the shortest
(2.28 Å) C→M bond lengths are related to the
[{Ph3PCHCOC5H4CN}→HgI] (3) and [{Ph3PCHCOC5-
H4CN}→HgCl] (1) complexes, respectively. These data
are in good agreement with the calculated interaction
energies (ΔEint) for all of these complexes. The ΔEint
between the studied phosphorus ylide {Ph3-
PCHCOC6H4CN} and Hg2X2 [X= Cl (1), Br (2), I (3)]
fragments in the optimized structures of [{Ph3PCH-
COC6H4CN}→HgX2]2 [X = Cl (1), Br (2), I (3)] were cal-
culated at the BP86/def2‐SVP level of theory according
to the following equation:
The interaction energies (ΔEint) between the ylidic part
of all complexes and Hg2X2 fragment (X = Cl, Br, I) are
illustrated in Table 5. The results show that the C→M
bond interaction energies are very strong and decrease
by changing the X atom from Cl to I in the phosphorus
ylide complexes in the following order: Cl > Br > I. These
results show that with decreasing electronegativity and S
character of carbon, there is a decrease in interaction
energy.
Regarding ΔEint, the [{Ph3PCHCOC6H4CN}→HgCl] (1)
and [{Ph3PCHCOC6H4CN}→HgI] (3) complexes have the
TABLE 5 ΔEint (kcal mol–1) for [{Ph3PCHCOC6H4CN}2→HgX2]2
(X = Cl, Br, I)
À
Á
ΔEint ¼ EAB– EAAB þ EBAB
(1)
Complex
ΔEint
[{Ph3PCHCOC6H4CN}→HgCl2]2
–135.33
where EAABstands for the electronic energy of the phospho-
rus ylide fragments and EBAB represents the electronic
energy of the Hg2X2 [X= Cl(1), Br(2), I(3)] fragments in
[{Ph3PCHCOC6H4CN}→HgBr2]2
[{Ph3PCHCOC5H4CN}→HgI2]2
–68.66
–55.16

SABOUNCHEI ET AL.
9 of 13
highest (–135.33 kcal mol–1) and the lowest (–55.16 kcal
mol–1) amount of interaction energies, respectively.
Larger interaction energies lead to a strong bond and
respective short C→M bond length (Table 5).
Further investigation about C→M bonding interaction
is performed using the NBO analysis. This method gives a
more accurate and quantitative determination about
C→M bonding interaction. The partial charge values of
the C(ylidic), Hg atom, and Hg2X4 fragment [X = Cl (1),
Br (2), I (3)] are illustrated in Table 6. Concerning
[{Ph3PCHCOC6H4CN}→HgX] [X = Cl (1), Br (2), I (3)]
complexes, the C(ylidic) and Hg fragment in complexes
carry negative and positive charges, respectively.
A comparison of the Wiberg bond indices (WBIs) for
C→Hg bonds in [{Ph3PCHCOC6H4CN}→HgX2]2 [X = Cl
(1), Br (2), I (3)] complexes is provided in Table 6. The
highest value of WBI (0.40) for C→Hg bonds is related
to the [{Ph3PCHCOC6H4CN}→HgCl2]2 (1) complex.
EDA is a suitable method to characterize the ionic and
covalent share of a distinct bond in a complex (Table 7).
The bonding analysis in terms of EDA of all the afore-
mentioned complexes was carried out at the
BP86/TZ2P(ZORA)//BP86/def2‐SVP level of theory with
C1 symmetry using the program package ADF2013.01.
In the EDA calculation, ΔEint consists of four main
parameters, which are illustrated in the following
equation:
is dispersion energy between two fragments. Table 7 pre-
sents the results of the EDA for all the aforementioned
complexes.
The strength and nature of donor–acceptor bonds
(C→M) of the two‐electron donor phosphorus
{Ph3PCHCOC6H4CN} ylide with HgX2 [X = Cl (1), Br
(2), I (3)] were compared. According to Table 6, C→M
bond interaction energies are very strong and they are
decreased by changing the X atom from Cl to I in phos-
phorus ylide complexes in the following order: Cl > Br
> I, respectively. This trend is predictable due to the
change in halogen electronegativity.
The interaction energies calculated from EDA are in
good agreement with those extracted from the aforemen-
tioned single‐point analysis, which also demonstrated Cl
> Br > I. Regarding equation (2), the more important fac-
tor in interaction energies (ΔEint) in these complexes is
electrostatic interaction (ΔEelstat) of about 49%–53%. This
share is about 32%–35% for orbital interactions. The larger
amounts of ΔEelstat are related to [{Ph3PCHCOC6-
H4CN}→HgCl] complexes in the following order:
[{Ph3PCHCOC6H4CN}→HgCl] > [{Ph3PCHCOC6H4CN}-
HgBr] > [{Ph3PCHCOC6H4CN}→HgI] (Table 7).
With respect to the EDA–NOCV method, individual
contributions of pairwise interactions are possible. The
most important ones are illustrated in Figure 3. The four
NOCV pairs regarding the [{Ph3PCHCOC6H4CN}→HgX2]2
complexes account for an average of 77% of ΔEorb
.
ΔEint ¼ ΔEelstat þ ΔEPauli þ ΔEorb þ ΔEdisp
(2)
The shapes of orbital pairs Δρ between the donor
orbital of ylide and the acceptor part of the Hg2X2 frag-
ments are shown in Figure 3. As can be seen, the σ
where ΔEelstat is electrostatic interaction, ΔEPauli is
Pauli repulsion, ΔEorb is orbital interaction, and ΔEdisp
TABLE 6 Wiberg bond indices (WBIs) of the C−M bond and natural charges of C and M atoms and MR′
Complex
WBI
Hg
C(carbene)
Hg2X2
[{Ph3PCHCOC6H4CN}→HgCl2]2
0.40
0.71
–1.02
–0.48
[{Ph3PCHCOC6H4CN}→HgBr2]2
[{Ph3PCHCOC6H4CN}→HgI2]2
0.36
0.34
0.59
0.38
–1.00
–0.98
–0.50
–0.52
Fragment in [{Ph3PCHCOC6H4CN}2→HgX2]2 (X = Cl, Br, I) at the BP86/def2‐SVP level of theory. Data in parentheses are related to the second carbon in the
complexes.
TABLE 7 EDA analysis [BP86/TZ2P(ZORA)//BP86/def2‐SVP] of [{Ph3PCHCOC6H4CN}2→HgX2]2 (X = Cl, Br, I) complexes with the C1
symmetry
Complex name
ΔEint ΔEPauli ΔEelstat
ΔEorb
ΔEdisp
–47.40
ΔEorb,σd ΔEorb,σd ΔEorb,σbd ΔEorb,σbd
[{Ph3PCHCOC5H4CN}→HgCl2]2 –135.82 253.00 –207.53
–134.55
(34.50)
–46.73
–35.56
–31.71
–44.38
–34.01
–30.45
–6.47
–4.94
–4.17
–6.50
–4.81
–3.89
(53.30)
(12.17)
–48.72
(15.64)
–52.39
(18.61)
[{Ph3PCHCOC5H4CN}→HgBr2] –112.75 198.64 –159.39
–103.27
(33.20)
(51.18)
2
[{Ph3PCHCOC5H4CN}→HgI2]2 –102.33 179.08 –138.42
–90.59
(32.19)
(49.20)
Data in parentheses are the number in percentage.
EDA, energy‐decomposition analysis; ΔEdisp, dispersion energy between two fragments; ΔEelstat, electrostatic interaction; ΔEint, interaction energies; ΔEorb
orbital interaction; ΔEPauli, Pauli repulsion; ΔEorb,σd, orbital interaction, σ‐donation; ΔEorb,σbd, orbital interaction, σ‐back donation.
,

10 of 13
SABOUNCHEI ET AL.
FIGURE 3 Deformation densities associated with the most important orbital interactions [{Ph3PCHCOC6H4CN}2→HgX2]2 (X = Cl, Br, I)
at the BP86/def2‐SVP level of theory
donation related to Δρ1 and Δρ2 is the dominant term
in ΔEorb and the σ back donation related to Δρ3 and
Δρ4 has only a minor effect on ΔEorb. It is thus clear
that there is no important π interaction in these
complexes.
3.5 | Antibacterial study
The antibacterial activity using the agar disc diffusion
method was determined for the synthesized phosphorus
ylide Y and mercury(II) complexes 1–4. The results of

SABOUNCHEI ET AL.
11 of 13
TABLE 8 Antibacterial activity of the ylide Y and its synthesized complexes 1–4
Compounds
Prevention area
Microorganisms
Y
1
2
3
4
Control
Gram negative
Gram positive
Escherichia coli
Pseudomonas fluorescens
Klebsiella oxytoca
NA
NA
18
15
22
19
16
15
22
18
20
17
20
18
NA
17
18
16
NA
NA
NA
NA
NA
Pseudomonas aeruginosa
7
Bacillus thuringiensis
Bacillus cereus
Staphylococcus aureus
Staphylococcus saprophyticus
Bacillus subtilis
NA
NA
NA
NA
NA
21
35
38
40
18
20
25
25
25
20
20
26
26
28
18
17
21
40
40
50
NA
NA
NA
NA
NA
NA, not applicable.
the antibacterial assessments, together with negative and
positive controls, are presented in Table 8. In this
research, the free ligand and especially the complexes
show good antibacterial activity against the bacteria
tested, in particular against gram‐positive bacteria.
indicate that the complexes studied may be used in the
treatment of diseases caused by the bacteria tested. How-
ever, further studies are needed to evaluate the in vivo
potential of these compounds in animal models.
The most effective compounds were HgCl2 and Hg
(NO3)2 complexes (1 and 4) against S. saprophyticus and
S. aureus (40‐mm inhibition zone). Mercury(II) nitrate
complex 4 showed the highest antibacterial activity
against B. subtilis (50 mm). Inhibition zones of the com-
pounds against S. saprophyticus and S. aureus were signif-
icantly larger than those of chloramphenicol (25 and 27
mm). These compounds also showed a wide inhibition
zone at a very low concentration. The lowest inhibition
zone was observed for the phosphorus ylide Y (7 mm)
against P. aeruginosa and K. oxytoca (18 mm). This ligand
did not show any antibacterial effect and inhibition zones
against all the other studied bacterial strains. However,
the synergistic or antagonistic effect of one compound,
present in minor percentage of a mixture, has to be con-
sidered as well.[67,68] The antibacterial activity can also
be influenced by the slow release of the ligands inside
the bacterial cell. We can consider that different coordina-
tion modes of the ligands to the metal complex may facil-
itate the ability of a metal complex to cross the lipid layer
of the bacterial cell membrane and in this way may affect
the mechanisms of growth and development of bacte-
ria.[69] A comparative study of the growth inhibition zone
values of the phosphorus ylide Y and mercury(II) com-
plexes 1–4 indicates that the complexes exhibit clearly
higher antibacterial activity than the free ligand Y. With
antibacterial activities of samples compared with those
of a reference antibiotic (chloramphenicol), it seems that
all complexes have remarkable inhibitory potencies
against bacterial species considered in this research
(Table 8). Although all bacteria tested are sensitive to
chloramphenicol, the antibacterial effects of some com-
plexes, especially HgCl2 and Hg(NO3)2 complexes 1 and
4, were higher than these antibiotics. These results
4 | CONCLUSIONS
The synthesis and characterization of organic/inorganic
composite polymer and binuclear Hg(II) complexes of a
new α‐keto‐stabilized phosphorus ylide are described. On
the basis of the physicochemical and spectroscopic data,
we propose that the ligand herein exhibits monodentate
C coordination to the metal center, which is confirmed by
the X‐ray crystal structure of the polymeric mercury(II)
nitrate complex 4 and theoretical study. The electronic
and molecular structure of mercury(II) halide complexes
1–3 have been studied by DFT at the BP86/def2‐SVP level
of theory. The nature of the C–Hg bond in complexes 1–3
was investigated using the NBO and EDA methods. The
results confirm that electrostatic interactions are the major
interactions among EDA components at about 49%–53%
while the share of orbital interactions is about 32%–35%
of total interaction energies. In addition, the antibacterial
studies of these compounds demonstrate that a group of
antimicrobial agents with potential application for the con-
trol of bacterial infections might be helpful in preventing
the progress of various infections and can be used as alter-
native systems for medicines.
ORCID
Seyyed Javad Sabounchei
9000-5304
https://orcid.org/0000-0001-
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SUPPORTING INFORMATION
[55] S. J. Sabounchei, A. Dadras, M. Jafarzadeh, H. R. Khavasi, Acta
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