31P NMR study of the stoichiometry, stability, and thermodynamic data for the complexation of several HgX2: acetylemethylene tripara tolyl phosphorane complexes in various tetrahydrofuran–dimethyl sulfoxide mixtures

Article abstract of DOI:10.1007/s13738-018-1496-7

Hg(II) halides are shown to react with the unsymmetrical phosphorus ylide, CH₃COCHP(p-tolyl)₃ (Y) to be shaped binuclear products with the composition {HgX₂[CH₃COCHP(p-tolyl)₃(Y)]}₂, where X = I, Br, and Cl. ³¹P NMR measurements were occupied to monitor the stability and stoichiometry of phosphorus ylide complexes with HgX₂ in binary tetrahydrofuran–dimethyl sulfoxide mixtures of changing composition. In all instance studied, the change of ³¹P chemical shift with the [HgX₂]/[Y] mole ratio showed the formation of 1:1 complexes. The stable constants of the arising from complexes were appraised from computer fitting of the mole ratio information to an equation that relates the monitored chemical shifts to the stable constant. In all solvent mixtures studied, the stabilities of the consequence 1:1 complexes varied in the order HgI₂ < HgBr₂ < HgCl₂. It was found that, in the instance of all complexes, an addition in the percentage of tetrahydrofuran in the solvent mixtures, consequentially increased the stability of the complexes. The temperature relation formation constants were used for the appraisal of the entropy and enthalpy values for the complexation reaction. It was deduced that in all complexes, the resulting complex enthalpy is made stable and entropy destabilized.

Full text of DOI:10.1007/s13738-018-1496-7

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-018-1496-7
ORIGINAL PAPER
31P NMR study of the stoichiometry, stability, and thermodynamic
data for the complexation of several HgX2: acetylemethylene tripara
tolyl phosphorane complexes in various tetrahydrofuran–dimethyl
sulfoxide mixtures
Mohammad Hasan Zebarjadian1 · Leila Vatannavaz2 · Seyyed Javad Sabounchei2
Received: 31 May 2018 / Accepted: 7 September 2018
© Iranian Chemical Society 2018
Abstract
Hg(II) halides are shown to react with the unsymmetrical phosphorus ylide, CH3COCHP(p-tolyl)3 (Y) to be shaped binu-
clear products with the composition {HgX2[CH3COCHP(p-tolyl)3(Y)]}2, where X=I, Br, and Cl. 31P NMR measurements
were occupied to monitor the stability and stoichiometry of phosphorus ylide complexes with HgX2 in binary tetrahydro-
furan–dimethyl sulfoxide mixtures of changing composition. In all instance studied, the change of 31P chemical shift with
the [HgX2]/[Y] mole ratio showed the formation of 1:1 complexes. The stable constants of the arising from complexes
were appraised from computer fitting of the mole ratio information to an equation that relates the monitored chemical shifts
to the stable constant. In all solvent mixtures studied, the stabilities of the consequence 1:1 complexes varied in the order
HgI2 <HgBr2 <HgCl2. It was found that, in the instance of all complexes, an addition in the percentage of tetrahydrofuran
in the solvent mixtures, consequentially increased the stability of the complexes. The temperature relation formation con-
stants were used for the appraisal of the entropy and enthalpy values for the complexation reaction. It was deduced that in
all complexes, the resulting complex enthalpy is made stable and entropy destabilized.
Keywords Acetylemethylene tripara tolyl phosphorane · Phosphorus ylide · Binuclear products · Stable constant ·
Tetrahydrofuran–dimethyl sulfoxide mixtures
Introduction
or the enolate oxygen (c). The enolate from (c) may assume
either a cis or trans arrangement, the geometry of which will
be retained upon bonding to the metal [3, 4].
The organometallic chemistry of phosphorus ylides R3P=C
(R׳) (R׳׳) (R, R׳, R״ = alkyl or aryl groups) has undergone
great growth over the last few years, mainly due to their
interesting application as reactants in organometallic and
metal-mediated organic synthesis [1, 2]. Adjacence of car-
banion and the keto group in the phosphorus ylide APPY
allows for resonance delocalization of the ylidic electron
density, providing additional stabilization to the ylide class
(Scheme 1). This so-called α-stabilization provides APPY
with the potential to act as an ambidentate phosphorus ylide
and thus bond to a metal center through either carbanion (b)
In the compounds informed to date, coordination through
carbon is more primary and is monitored with soft metal
ions, e.g., Hg(II), Pd(II), Pt(II), Ag(I), Au(I), and Au(III)
[5–9] and only very few examples of O-coordinated ylides
are known [10, 11]. Cretain of these examples contain the
ylide O-coordinated to a hard, very oxophilic metal center,
such as Sn(IV) [10, 12] or group 4 metals with a high
oxidation number, e.g., Ti(IV), Zr(IV), and Hf(IV) [12].
Solely W(0) complexes of the type W(CO)5L (L = ylide)
[13] and Pd(II) complexes of the stoichiometry [Pd(C6F5)
L2)(APPY)](ClO4) [14] [APPY = Ph3CCOMe; L = PPh3,
PBu3; L2 = bipy] contain stable ylides O-linked to a soft
metal center. We have lately centered on the stability and
formation of a number of binuclear complexes extracted
from mercury(II) salts and phosphorus ylides [15–19]. This
inclusive definition comprises nearly all kind of possible
* Mohammad Hasan Zebarjadian
zebarjadian@gmail.com
1
Farhangian University, Hamedan 6513666157, Iran
2
Faculty of Chemistry, Bu-Ali Sina University,
Hamedan 65174, Iran
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
Experimental
Mercury salts were obtained from the Aldrich. Tetrahydro-
furan (THF) and dimethyl sulfoxide (DMSO) were com-
mercially available from the Merck and used as received.
acetylemethylene tripara tolyl phosphorane (Y) was do
as previously delineated [15, 16] by the reaction of con-
nected phosphine with 2-bromo-4ʹ-chloroacetophenone
and attendant elimination of HBr by NaOH. The charac-
teristic of the solvents used in these research is given in
Table 1 [21–25].
Scheme 1 Canonical formats of APPY (R=CH3)
di- or poly-dentate phosphorus ylides but in this paper our
intention is to center our point of view on the coordination
chemistry of the acetylemethylentriparatolylphosphorane (L)
(scheme 2) [16].
All NMR studies were made on a FX90Q JEOL NMR
spectrometer with a field power of 2.35T supplied with
a temperature controller, ( 0.1 °C). At this system, 31P
resonates at 36.26 MHz characteristic acquisition param-
eters were 5000 Hz sweep width, 500 scans, 2 s relaxa-
tion delay, 2 s acquisition time, 24 μs pulsewidth (45°
pulse), and 64 k = 65,536 words with proton decoupling
in 89.90 MHz. In 31P NMR studies, the standard was 85%
H3PO4. Stock solutions of the acetylemethylene tripara
tolyl phosphorene (Y) were rigged by weighting a suit-
able amount of the phosphorus ylide at concentrations of
0.01 M in binary tetrahydrofuran–dimethyl sulfoxide mix-
tures of changing composition. Allot quantities of metal
salts at concentrations of 0.10 M dissolved in the referred
to solvents were added up to the [HgX2]/[Y] mole ratio of
4, using a micro-syringe. After blending of the solutions
beneath ultrasonic for 10 min, their 31P NMR spectra were
registered at 20.0, 35.0, 50.0, and 60.0 ( 0.1) °C.
Our benefit in the physico-chemical properties of the
phosphorus ylide encouraged us to study (in recent years,
we have introduced) some of spectrophotometric methods
for the evaluation of the formation constants of some tran-
sition metal cations with new synthetic phosphorus ylide,
formation, and stability of a number of mercuric salts phos-
phorus ylide complexes in different solvents [17, 18]. In this
research, we utilized 31P NMR as a very exquisite probe
to study the complexation of HgI2, HgBr2, and HgCl2 with
acetylemethylene tripara tolyl phosphorane (Y) in binary
tetrahydrofuran–dimethyl sulfoxide mixtures of changing
composition. We experienced to use Hg(NO3)2 salt for col-
lation in this proses, but this salt does not solve in utilized
solvents. It should be sizeable that mercuric ions used have
unsuitable NMR properties such as insensitive chemical
shift, low receptivity [20], high quadrupole moment, etc.
Scheme 2 X=Cl−, Br−, and I−
X= Cl-, Br- and I-
Table 1 Properties of the
Solvent
Viscosity
Had
μ
D
DN
AN
8.0
20.4
bp (oC)
mp (oC)
solvents
THF
DMSO
0.48
2.00
1.407
1.479
1.63
3.96
7.5
47.2
20.0
29.8
66
189
−108.4
18.5
μ dipole moment in Deby units, D dielectric constant (25 °C), DN Gutmann donor number(kcal mol−1), AN
acceptor number(kcal mol−1), Bp boiling point, Mp melting point
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Journal of the Iranian Chemical Society
ylide—mercuric ion is equal to 1, indicating the forma-
tion of a relatively stable complex. Usually, the behavior
of the 31P chemical shift as a function of [HgX2]/[Y] mole
ratio shown in Figs. 2 and 3 can be nearly divided into
two groups: (1) the downfield shift changes linearly with
the [HgX2]/[Y] mole ratio until a mole ratio of about 1
is reached; more increase of the phosphorus ylide does
not alter the resonance frequency. Similar behavior,
which is clearly monitored for total mercuric salts in pure
THF (Fig. 3e), binary %75 THF and %50 THF mixtures
(Fig. 3d, c) are showing of normal stable 1:1 complex in
solution. (2) A progressive paramagnetic chemical shift
of the 31P resonance with raising phosphorus ylide con-
centration that does not display any tendency to level off
become even at a mole ratio of four. Such behavior, which
is monitored for total mercuric salts in binary 25% THF
(Fig. 3b) and pure DMSO (Fig. 3a), emphasizes the forma-
tion of a weaker than 1:1 complex between (Y) and HgX2.
The now study depicts the stability and formation of a
series of dimeric mercury(II) complexes extracted from
phosphorus ylides and mercuric halides. On the basis of
the spectroscopic NMR data and physico-chemical, we
suggest that the phosphorus ylides here show monoden-
tate C-coordination toward the metal central, what was
antecedently approved by the X-ray crystal structure of the
complexes. Theoretical studies in the gas phase indicate
that the observed the possible cis-like structures for the
present complexes are always less stable than trans-like
structures [16].
Results and discussion
NMR spectroscopy has been greatly used to the stability
and stoichiometry studies [26–29]. The chemical shifts are
measurable factor used for these researches. The 31P chem-
ical shifts of 0.01 M phosphorus ylide solutions in differ-
ent tetrahydrofuran and dimethyl sulfoxide mixtures were
observed as a function of [HgX2]/[Y] ratio up to a molar
ratio of 4. Sample spectra are demonstrated in Fig. 1. In all
cases, only one population averaged resonance was moni-
tored and one signal form arises from a fast interchange
between complexed and free phosphorus ylide [Y] on the
NMR time scale [30–34].
The arise from 31P chemical shift—mole ratio plots
for different Phosphorus ylide—HgX2 systems in various
tetrahydrofuran–dimethyl sulfoxide mixtures in 20 and
35 °C are shown in Figs. 2 and 3. As can be seen from
Figs. 2 and 3, increasing the concentration of the ylide to
the HgX2 solution gently shifts the comparable 31P reso-
nance of phosphorus ylide downfield, to the [HgX2]/[Y]
mole ratios abreast about 1. This behavior clearly shows
the formation of 1:1 (MY) complexes in solution under
total studied conditions.
The same conclusion was acquired for this reaction in
X-ray crystal structure and theoretically the gas phase of
complexes of [HgBr2-Y]2 [16]. In total instances, addi-
tion of the ylide solution to HgX2 causes a nearly linear
paramagnetic shift that commences to level off at mole
ratios > 1. The slant of the analogous mole ratio plots
changes meaningfully at the point where the phosphorus
The stable constants of 1:1 complexes were computed
from the variation of the 31P chemical shift [HgX2]/[Y] mole
Fig. 1 31P spectra of a 0.01 M solution of phosphorus ylide in 20.0 °C at various a [HgI2]/[Y] mole ratios in dimethyl sulfoxide and b [HgCl2]/
[Y] mole ratios in tetrahydrofuran
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Journal of the Iranian Chemical Society
24
22
20
18
16
14
12
10
22
20
18
16
14
12
10
A
B
0
1
2
3
4
0
1
2
3
4
[M]/[L]
22
20
18
16
14
12
10
C
0
1
2
3
4
[M]/[L]
Fig. 2 31P chemical shifts as a function of the a [HgCl2]/[Y], b [HgBr2]/[Y], and c [HgI2]/[Y] mole ratio in various tetrahydrofuran–dimethyl
sulfoxide mixtures in 20 °C
ratio. It has been shown antecedently [25] that the monitored
chemical shift is given by
KINFIT schedule results from the high degree of confidence
in this program [37].
ꢀ
ꢀobs
=
[(Kf CHgY − Kf − Kf CY − 1) + (Kf2CY2 + Kf2C2
− 2Kf2CYCHgX + 2Kf CY + 2Kf CHgX + 1)1∕2
]
HgX2
2 2
2
}
(1)
× (ꢀY − ꢀHgX −Y)∕2KHgX CHgX + ꢀHgX −Y
,
2
2
2
2
where Kf is the stable constant for the 1:1 complex, CHgX and
Therefore, from the data exhibited in Table 2, it is immedi-
ately apparent that for a given phosphorus ylide the stability of
the resulting complex is related on the solvent mixture compo-
sition. In total instances, the stability increases consequently
with increasing amount of THF in the solvent mixture. It has
been well substantiated that the solvating capability of the
solvent, as explicated by the Gutmann donor number [25] and
dielectric constant, acts a key function in different complexa-
tion reactions [37–49]. It should too be noted that an inten-
sify in the dielectric constant causes an increase in the bond
formation. It is well known that DMSO as a solvent of high
solvating capability (DN=29.8, D=47.2) competes with the
phosphorus ylide for the mercuric salts much more than THF
as a low density solvent (DN=20.0, D=7.5). Therefore, it is
2
CY are the analytical concentrations of the mercuric salt and
Y, respectively, and ꢀHgX −Y and ꢀY are the respective chemi-
2
cal shifts of the complexed and free phosphorus ylide. Stable
constants of the resulting 1:1 complexes were computed by
fitting the resulting chemical shift—mole ratio plots, with
the KINFIT schedule [35, 36]. A specimen computer fit of
the 31P chemical shift–mole ratio data is displayed in Fig. 4,
and acquired Log Kf for complexation of HgX2 with Y under
total the conditions are displayed in Table 2. An equitably
agreement between the calculated and monitored chemical
shifts shown in Fig. 4 that are more supports for the forming
of a complex with 1:1 stoichiometry between Y and HgX2.
The great trust in the interval of logKf, as accounted by the
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Journal of the Iranian Chemical Society
Fig. 3 31P chemical shifts as a function of the [HgX2]/[Y] mole ratio in various 100% DMSO a, 75% DMSO—25% THF b, 50% DMSO—THF
c, 25% DMSO—75% THF d, and 100% THF e solutions in 35 °C
Fig. 4 Computer fit of 31
P
chemical shift vs. [HgCl2]/[Y]
mole ratio in tetrahydrofuran in
20 °C, (x) experimental point;
(o) calculated point; (=) experi-
mental and calculated points are
the same within the resolution
of the plot
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Journal of the Iranian Chemical Society
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Journal of the Iranian Chemical Society
not unexpected that addition of DMSO to THF will reduce the
stability of the [HgX2–Y]2 complexes.
are enthalpy stabilized. In addition, the ∆G values demon-
strate that complexation reactions are totally spontaneous. It
was admitted that stability of the resulting complexes power-
fully depends on the quantity of DMSO in the solution. The
formation constant of the complexes was reduced by increas-
ing DMSO amount. Total complexes in THF solutions were
determined to be more stable than those in THF–DMSO
mixture solutions and pure DMSO solvent. Since the ther-
modynamic data summarized in Table 2, it is deduced that
against the Gibbs free energy and enthalpy, the entropy of
total complexes acted as a factor uncomfortable in all sol-
vents. In addition, the resulting complex is mainly enthalpy
stabilized in THF, 75% THF −25% DMSO, while in the 50%
THF–DMSO, the enthalpy is nearly the singular contribu-
tor in the Gibbs free energy of the reaction [31]. Although
in this matter, the solvating ability of the solvent increased
and the dielectric constant are decreased, lower energy will
need to be disconnected the cation and anion. Thus, lower
enthalpy and Gibbs free energy were obtained in THF and
%75 THF–25% DMSO as a result of the solvating ability of
the solvent and the lower dielectric constant for THF [52,
53]. However, the different entropy and enthalpy of the reac-
tion in two solvents would be explained in terms of differ-
ent solvent–complex interactions, in these media. THF with
The information given in Table 2 clearly shows that, in a
given THF–DMSO mixture, the stability of HgX2 complexes
increases in the command HgI2–Y<HgBr2–Y<HgCl2–Y.
In reality, where the frame remainders the same, the stable
constants on the resulting complexes increase in the order
THF to DMSO solvents. The presence of I− ion would cause
an important decrease in the formation of the resulting com-
plex, compared with Br− and Cl− ions–phosphorus ylide.
These consequences clearly illustrate the fundamental role
of the different counter ions on complex formation constant
[50, 51]. It is useful to regard the enthalpy and entropic con-
tributions of the reaction in command to have a more than
comprehending of the thermodynamic of the complexation.
Hence, the ∆H and ∆S values were calculated from the slope
and take of the van’t Hoff plot, separately (Eq. 2):
( )
T
1
2.303R log Kf = −ΔH
+ ΔS.
(2)
The van’t Hoff plots of log Kf against 1/T for the com-
plexes in THF–DMSO mixture solution are explained in
Fig. 5. The obtained ∆H and ∆S values are recorded in
Table 2. These results display that the HgX2–Y complexes
Fig. 5 Van’t Hoff plot for the
complexation reaction between
Y with HgX2 in (a) THF, (b)
75% THF—25% DMSO, (c)
50% THF—DMSO, (d) 25%
THF—75% DMSO, and (e)
DMSO
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Journal of the Iranian Chemical Society
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