Effect of Organic Solvents on the Rate of Oxidation of Sulfoxides with Peroxy Acids

Article abstract of DOI:10.1134/S1070363220030020

Abstract: The reaction of sulfoxides with peroxy acids in various organic media was studied. The reaction mechanism involves the rapid formation of a sulfoxide-–peroxy acid intermediate which decomposes in the second stage to form carboxylic acid and the corresponding sulfone. The second stage is the rate-limiting step. The reaction medium significantly affects the rate of oxidation. The calculated activation parameters of the oxidation process indicate a compensation effect in the investigated reaction. Correlations between the main physicochemical parameters of solvents and the effective rate constants (k) of dimethyl sulfoxide oxidation with peroxy acids were found. Depending on the reaction conditions, the main factors affecting the k values are specific and nonspecific solvation of the reactants and structural factors.

Full text of DOI:10.1134/S1070363220030020

ISSN 1070-3632, Russian Journal of General Chemistry, 2020, Vol. 90, No. 3, pp. 329–334. © Pleiades Publishing, Ltd., 2020.
Russian Text © The Author(s), 2020, published in Zhurnal Obshchei Khimii, 2020, Vol. 90, No. 3, pp. 338–345.
Effect of Organic Solvents on the Rate of Oxidation
of Sulfoxides with Peroxy Acids
a,
b
a
c
V. S. Dutka *, G. G. Midyana , Yu. V. Dutka , and E. Ya. Pal’chikova
a
Franko Lviv National University, Lviv, 79601 Ukraine
b
Physical Chemistry of Combustible Minerals Department, Lytvynenko Institute of Physical Organic and Coal Chemistry,
National Academy of Science of Ukraine, Lviv, 79060 Ukraine
c
Institute of Geology and Geochemistry of Fossil Fuels, National Academy of Science of Ukraine,
Lviv, 79060 Ukraine
*
e-mail: vdutka@ukr.net
Received September 3, 2019; revised September 3, 2019; accepted September 6, 2019
Abstract—The reaction of sulfoxides with peroxy acids in various organic media was studied. The reaction
mechanism involves the rapid formation of a sulfoxide–peroxy acid intermediate which decomposes in the sec-
ond stage to form carboxylic acid and the corresponding sulfone. The second stage is the rate-limiting step. The
reaction medium significantly affects the rate of oxidation. The calculated activation parameters of the oxidation
process indicate a compensation effect in the investigated reaction. Correlations between the main physicochemical
parameters of solvents and the effective rate constants (k) of dimethyl sulfoxide oxidation with peroxy acids were
found. Depending on the reaction conditions, the main factors affecting the k values are specific and nonspecific
solvation of the reactants and structural factors.
Keywords: sulfoxides, peroxy acids, influence of solvents, correlation equations
DOI: 10.1134/S1070363220030020
Oxidation of sulfides to sulfoxides with peroxy
peroxydodecanoic, and peroxypentanoic acids were taken
as oxidants. Preliminary kinetic experiments showed the
first order of the reaction in each component and overall
second-order kinetics. The oxidation process involves two
stages. The first stage is fast formation of a sulfoxide–
peroxy acid intermediate which decomposes in the second
stage to give the corresponding acid and sulfone. The
compounds is widely used in practice [1–3]. In turn,
sulfoxides can be oxidized to sulfones. In most cases,
hydroxide peroxide is used as oxidant, and sometimes
catalytic systems consisting of hydrogen peroxide and
an appropriate catalyst are utilized [4, 5]. Peroxy acids
have a number of advantages over traditional oxidants
in the oxidation of organic sulfides, nitrogen-containing
aromatics, and ethylene derivatives [6–8]. The oxidation
of sulfoxides with peroxy acids provides higher yields of
sulfones. The solvent used as reaction medium affects
both the oxidation rate and product yield. Oxidation
of sulfoxides with various oxidants such as benzoyl
peroxide and hydrogen peroxide was reported [9–11].
The oxidation of sulfoxides with peroxy compounds
was shown [12–14] to proceed as a typical electrophilic
reaction. The role of solvent in such processes has been
poorly studied, though the solvent should be expected to
affect both reaction rate and yield.
first stage is reversible (K ), while the second stage is
eq
rate-determining (k ). The solvent affects both stages of
ef
the oxidation process.
Table 1 contains the rate constants k for the oxidation
of sulfoxides with peroxy acids, which were determined
in the initial period of the process. It is seen that neither
sulfoxide nor peroxy acid nature affects the reaction
rate to an appreciable extent. The apparent energies of
activation (E ) are similar, and they range from 36.0
a
to 40.2 kJ/mol for the reactions in ethyl acetate. The
kinetics of oxidation of dimethyl sulfoxide (DMSO)
with peroxydecanoic acid were studied in 11 solvents in
the temperature range 298–318 K. The highest reaction
rate at 298 K was observed in benzene, whereas the rate
constant k in acetic acid was lower by approximately an
In this work we used dimethyl sulfoxide, dibutyl
sulfoxide, and diphenyl sulfoxide as substrates, and
peroxydecanooc, peroxynonanoic, peroxybenzoic,
3
29

330
DUTKA et al.
Table 1. Effective rate constants for the oxidation of sulfoxides with peroxy acids in ethyl acetate
k×10 , L mol s–1
3
a
–1
b
Sulfoxide
DMSO
DMSO
DMSO
Peroxy acid
E , kJ/mol
a
2
98 K
308 K
48.0
46.6
45.6
47.5
48.5
45.1
44.2
45.2
318 K
80.0
78.4
75.2
72.2
81.6
76.0
71.2
75.2
Peroxydecanoic acid
Peroxynonanoic acid
Peroxybenzoic acid
Peroxypentanoic acid
Peroxydecanoic acid
Peroxydecanoic acid
Peroxybenzoic acid
Peroxydodecanoic acid
29.8
29.2
28.3
29.5
30.1
28.0
26.8
28.3
39.4
39.5
39.2
36.0
40,2
40.1
39.3
39.4
DMSO
Dibutyl sulfoxide
Diphenyl sulfoxide
Diphenyl sulfoxide
DMSO
a
Δk = ±0.03k.
b
The E values were determined with an accuracy of ±5.0 kJ/mol.
a
Table 2. Effective rate constants for the oxidation of DMSO with peroxydecanoic acid in different solvents at different temperatures
k×10 , L mol s–1
3
a
–1
Solvent
Acetic acid
Propan-2-ol
Dimethylformamide
Acetone
2
98 K
303 K
7.08
12.5
24.4
35.6
37.2
37.6
45.0
48.4
52.0
57.8
53.2
68.0
308 K
9.70
17.4
33.0
45.2
51.6
48.0
62.8
69.4
68.0
78.8
71.8
87.6
313 K
13.5
23.0
43.8
56.0
68.6
64.0
–
98.4
98.4
109
94.6
106
318 K
16.3
36.8
54.6
66.6
97.8
80.0
107
133
130
152
121
5.24
8.46
18.9
27.2
27.8
29.8
33.8
35.2
38.4
40.4
46.8
55.2
Chloroform
Ethyl acetate
1
,2-Dichloroethane
Nitrobenzene
Carbon tetrachloride
Chlorobenzene
1
,4-Dioxane
Benzene
145
a
Δk = ±0.03k.
order of magnitude (Table 2). Our results suggest that the
products do not influence the reaction rate.
of reactions of these compounds with peroxy acids is
similar.
≠
≠
It should be noted that in our experiments peroxy-
decanoic acid was not consumed for side reactions.
This is very consistent with our previous data [15, 16]
according to which thermal decomposition of peroxy
acids in organic solvents begins at a considerably higher
temperature.
The ΔH and ΔS values for the transition state are
related to each other, indicating a compensation effect.
≠
≠
The linear relation ΔH = f(ΔS ) suggests a complicated
character of the solvent influence on the rate of oxidation
of DMSO with peroxydecanoic acid. The isokinetic
temperature was estimated at 323±5 K, which is slightly
beyond the experimental temperature range. It should
be noted that the rates of oxidation of sulfides with
peroxy acids are significantly higher than the rates of
oxidation of sulfoxides. Depending on the conditions, the
oxidation rate constant of bis(4-chlorophenyl) sulfide with
peroxybenzoic ranges from 0.5 to 1.0 L mol s [18],
whereas the rate constants determined in our experiments
varied from 5.24×10 to 55.2×10 L mol
298 K (Table 2).
The apparent energies of activation and transition
state parameters were calculated from the temperature
dependences of the effective oxidation rate constants
(
Table 3). The apparent energies of activation (E) for the
oxidation of DMSO in the examined solvents vary from
1.6 to 57.1 kJ/mol and are close to the reported values
–
1 –1
3
for the oxidation of nitrogen-containing heterocyclic
compounds, epoxidation of olefins, and oxidation of
sulfur-containing compounds [9, 17–19]. The mechanism
–
3
–3
–1 –1
s
at
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 3 2020

EFFECT OF ORGANIC SOLVENTS ON THE RATE OF OXIDATION
331
Table 3. Activation parameters of the oxidation of dimethyl sulfoxide with peroxydecanoic acid in different solventsa
b
≠
–ΔS , J mol K–1
≠
–1
≠
Solvent
Acetic acid
Propan-2-ol
Dimethylformamide
Acetone
E , kJ/mol
ΔH , kJ/mol
ΔG , kJ/mol
85.8
a
44.9
53.9
43.2
36.1
48.0
39.4
46.7
52.2
44.7
52.3
42.7
37.7
42.4
51.4
40.7
33.6
45.5
36.9
44.2
49.7
42.2
49.8
40.2
35.2
146
112
141
162
121
150
124
105
130
104
135
150
84.6
82.7
81.8
81.7
81.5
81.2
81.1
80.9
Chloroform
Ethyl acetate
1
,2-Dichloroethane
Nitrobenzene
Carbon tetrachloride
Chlorobenzene
80.8
80.4
80.0
1
,4-Dioxane
Benzene
a
≠
≠
≠
The ΔH , ΔS , and ΔG values were calculated for a temperature of 308 K.
b
The E values were determined with an accuracy of ±5.0 kJ/mol.
a
The rate constants for the oxidation of sulfoxides are
the oxidation of DMSO at 298 K and solvent parameters.
The multiple correlation coefficient R was equal to 0.9780
which corresponds to a good correlation.
comparable to those found for the oxidation of olefins
with peroxy acids [17]. According to the data of [19],
the effective rate constants for the oxidation of olefins
with peroxybenzoic acid in various solvents range
2
log k = 3.0531 + (5.7263±1.5554) f(n ) + (1.6635±0.3679)f(ε)
+ (0.0016±0.0005)B – (0.0016±0.0005)E
T
–
3
–3
–1 –1
2
–
(0.0018±0.0007)δ – (0.0082±0.0031)V ;
(2)
from 9.0×10 to 0.3×10 Lmol s . These values are
close to those found by us for the oxidation of DMSO
with peroxydecanoic acid. The rates of the reactions of
M
N = 12, R = 0.9780, S = ±0.0633, F = 75.8515.
Here, N is the number of solvents, S is Studentʼs t test,
and F is Fisherʼs test. The pair correlation coefficients
3
peroxydecanoic acid with α-pinene and Δ -carene in
various organic solvents also approached the rates of
oxidation of DMSO with peroxy acids [17].
(r ) are 0.5929, –0.4662, –0.4133, –0.9155, –0.5104,
i
and 0.742, respectively. Analysis of Eq. (2) shows that
2
the parameters V and δ are insignificant. Successive
We used the known six-parameter correlation equa-
tion (1) [16, 20] to find correlations between the oxidation
rate constants (k) and transition state parameters, on the
one hand, and solvent parameters, on the other.
M
removal of these parameters slightly reduced the R value
to 0.9640 and 0.9542, respectively. As a result, four-
parameter correlation (3) was obtained:
log k = 3.0387 + (1.4182±1.1635)f(n2)
+ (0.9100±0.4136)f(ε) + (0.0002±0.0004)B
2
2
log k = a + a (n – 1)/(n + 2) + a (ε – 1 )/(2ε + 1)
0
1
2
2
+
a B + a E + a δ + a V .
(1)
3
4
T
5
6 M
–
(0.0584±0.0080)ET;
(3)
Here n and ε are, respectively, refractive index and
dielectric constant of a solvent, which characterize its
polarizability and polarity that are factors responsible
for nonspecific solvation. The Palʼm basicity parameter
N = 12, R = 0.9542, S = ±0.0908, F = 36.8334.
From the kinetic data obtained at 303 K, we
constructed correlation (4) with a multiple correlation
coefficient of 0.9798:
B [21] and Reichardt electrophilicity parameter E [22]
T
2
log k = 3.0299 + (4.8813±1.4321)f(n ) + (1.6387±0.3388)f(ε)
characterize acid–base properties of a solvent, i.e., its
specific solvation ability. The effect of structural factors
+
(0.0011±0.0005)B – (0.0592±0.0085)E
T
2
2
–
(0.0014±0.0006)δ – (0.0064±0.0029)V ;
(4)
is characterized by the Hildebrand parameter δ (δ is
M
N = 12, R = 0.9798, S = ±0.0582, F = 19.9728.
proportional to the cohesive energy density of a solvent)
and molar volume V . The solvent parameters were taken
The pair correlation coefficients (r ) for Eq. (4) are
M
i
from [23, 24], and the results are presented according to
0.6307, –0.4321, –0.4570, –0.9101, –0.5059, and 0.7740,
respectively.
[
25].
On the basis of Eq. (1) we obtained six-parameter
correlation (2) between the effective rate constants for
2
Exclusion of insignificant parameters B, δ , V , and
M
f(n) gave two-parameter correlation (5) with R = 0.9545:
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 3 2020

332
DUTKA et al.
log k = 3.5948 + (1.2007±0.3748)f(ε) – (0.0620±0.0065)E ; (5)
are insignificant. Their exclusion from the correlation
gave Eq. (11) with a slightly lower multiple correlation
coefficient, R = 0.9697.
T
N = 12, R = 0.9545, S = ±0.0868, F = 38.6580.
Likewise, the effective rate constants measured at
2
3
08 K were approximated by six-parameter correla-
log k = 2.9026 + (2.5839±0.7761)f(n ) + (0.9713±0.3145)f(ε)
tion (6) with a multiple correlation coefficient R of 0.9758,
– (0.0502±0.0062)ET;
(11)
which indicates a good correlation.
N = 12, R = 0.9697, S = ±0.0705, F = 58.0793.
2
log k = 2.9813 + (5.0421±1.5441)f(n ) + (1.5969±0.3653)f(ε)
We also tried to find a correlation between the energy
+
–
(0.0010±0.0005)B – (0.0569±0.0092)E
(0.0013±0.0007)δ – (0.0062±0.0031)V ;
T
of activation (E ) and solvent parameters. Six-parameter
a
2
(6)
M
correlation (12) was characterized by a low multiple
correlation coefficient, R = 0.8563. The latter was
improved to 0.9489 by excluding the data for dioxane,
and further exclusion of the data for chlorobenzene gave
Eq. (12) with R = 0.9883.
N = 12, R = 0.9758, S = 0.0628, F = 16.6142.
The pair correlation coefficients (r ) are 0.6607,
i
–
0.4148, –0.4698, –0.8968, –0.4853, and 0.7805,
respectively.
2
Analysis of Eq. (6) showed that the solvent parameters
log E = 1.3311 – (2.1575±0.2419)f(n ) – (0.1516±0.0517f(ε)
a
2
B, δ , and V insignificantly affect the oxidation of
– (0.0013±0.0001)B + (0.0056±0.0013)E
+ (0.0012±0.0001)δ + (0.0039±0.0004)V ;
N = 10, R = 0.9883, S = 0.8940, F = 7.2413.
M
T
2
DMSO. After exclusion of these parameters, we arrived
at three-parameter correlation (7):
(12)
M
2
log k = 2.9583 + (1.8267±0.8705)f(n ) + (1.0478±0.3528)f(ε)
The pair correlation coefficients (r ) are 0.2867,
i
–
(0.0535±0.0070)ET;
(7)
0.3133, –0.1030, 0.3655, 0.4260, and 0.0426, respectively.
Successive exclusion of insignificant parameters δ and
2
N = 12, R = 0.9614, S = ±0.0791, F = 45.9270.
Six-parameter correlation (8) obtained for the
effective rate constants of DMSO oxidation at 313 K
was characterized by R = 0.9842, which corresponds to
a good correlation:
ET reduced the R value to 0.9799 and 0.9663, respectively,
for four-parameter Eq. (13):
2
log E = 1.6309 – (2.4855±0.3837)f(n ) – (0.0015±0.0002)B
a
2
+
(0.0014±0.0001)δ + (0.0028±0.0006)V ;
(13)
M
2
log k = 2.7883 + (4.8335±1.2367)f(n ) + (1.3905±0.2935)f(ε)
N = 10, R = 0.9663, S = 0.0148, F = 262.8374.
+
–
(0.0009±0.0004)B – (0.0513±0.0074)E
(0.0012±0.0005)δ – (0.0040±0.0025)V ;
T
The six-parameter correlation between the solvent
parameters and ΔH was poor (R = 0.8561). The
correlation was improved by excluding the data obtained
in dioxane and chlorobenzene (R = 0.9898), which led
to Eq. (14):
2
≠
(8)
M
N = 12, R = 0.9842, S = ±0.0503, F = 112.2226.
The pair correlation coefficients (r ) are 0.6899,
0.4237, –0.4874, –0.9061, –0.4875, and 0.8156,
respectively. The parameters B, δ , V , and f(n) almost
i
–
2
≠
M
log ΔH = 1.2876 – (2.2896±0.2566)f(n)
do not affect the DMSO oxidation process at 313 K.
Exclusion of these parameters from correlation gave two-
parameter Eq. (9) with a multiple correlation coefficient
R of 0.9532.
–
+
(0.1615±0.0548)f(ε) – (0.0014±0.0001)B
2
(0.0060±0.0013)E + (0.0013±0.0001)δ
T
+
(0.0042±0.0004)VM;
(14)
N = 10, R = 0.9898, S = 0.087, F = 791.6524.
log k = 3.7918 + (1.2036±0.3708)f(ε) – (0.0606±0.0065)E ; (9)
T
The pair correlation coefficients (r ) are 0.2869, 0.3133,
i
N = 12, R = 0.9532, S = ±0.8532, F = 44.7247.
–0.1040, 0.3651, 0.4253, and 0.0423, respectively.
From the kinetic data for the oxidation of DMSO at
18 K we obtained correlation (10) with R = 0.9712:
Analysis of Eq. (14) showed that the parameters
≠
3
f(ε) and E do not affect the ΔH value. Exclusion of
T
2
the corresponding terms gave four-parameter correla-
tion (15):
log k = 2.9568 + (3.5706±1.6915)f(n ) + (1.1538±0.4001)f(ε)
+
–
(0.0003±0.0006)B – (0.0509±0.0101)E
(0.0004±0.0007)δ – (0.0019±0.0034)V ;
N = 12, R = 0.9712, S = ±0.0688, F = 61.0359.
T
2
≠
2
(10)
log ΔH = 1.6048 – (2.6355±0.4068)f(n ) – (0.0015±0.0002)B
M
2
+ (0.0015±0.0001)δ + (0.0030±0.0006)V ;
(15)
M
N = 10, R = 0.9663, S = 0.0158, F = 247.9917.
The pair correlation coefficients (r ) are as follows:
i
0
0
.7162, –0.4110, –0.5130, –0.8898, –0.4595, and
.8282, respectively. Here, the terms B, δ , and VM
Apoor correlation (R = 0.8481) was obtained between
the entropy of activationΔS and six solvent parameters.
2
≠
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 3 2020

EFFECT OF ORGANIC SOLVENTS ON THE RATE OF OXIDATION
333
≠
Since the ΔS values are negative, the sign was not taken
were purified as described in [28, 29] and distilled under
argon. Dimethyl sulfoxide was additionally purified by
recrystallization under argon.
into account. The correlation quality was improved to
R = 0.9860 after exclusion of the data for dioxane and
chlorobenzene.
The kinetics of oxidation of sulfoxides with peroxy
acids were studied in a glass reactor under argon in the
temperature range from 298 to 318 K. A reactor was
charged with a solution of peroxy acid with a required
concentration and placed in a thermostat where a
required temperature was maintained with an accuracy of
≠
2
logΔS = 2.4473 + (1.9418±0.3026)f(n ) – (0.0090±0.0648)f(ε)
(0.0013±0.0001)B – (0.0030±0.0016)E – (0.0012±0.0001)δ
2
–
T
–
(0.0041±0.0005)VM;
(16)
N = 10, R = 0.9860, S = 0.0102, F = 606.9405.
The pair correlation coefficients (r ) for Eq. (16)
are –0.5129, –0.2434, 0.2647, –0.1021, –0.3034, and
0.3134, respectively. By excluding insignificant terms,
f(ε) and E , we obtained four-parameter correlation (17)
with a slightly low multiple correlation coefficient (R =
i
±
0.05 K.Asolution of the corresponding sulfoxide in the
same solvent was quickly added, assuming this moment
as reaction onset. Samples were withdrawn from the
mixture at definite time intervals, and the concentration
of unreacted peroxy acid was determined by iodometric
titration according to [30]. In all cases, the error in the
determination of effective rate constants did not exceed
–
T
0
.9788).
≠
2
log ΔS = 2.2639 + (2.2415±0.3262)f(n ) + (0.0014±0.0001)B
2
+
(0.0014±0.0001)δ + (0.0037±0.0005)V ;
N = 10, R = 0.9788, S = 0.0126, F = 388.7232.
(17)
M
±
3%.
≠
CONFLICT OF INTEREST
The Gibbs energy of the transition state (ΔG ) was
approximated by six-parameter Eq. (18) with R = 0.9758
The authors declare the absence of conflict of interest.
REFERENCES
and the following pair correlation coefficients (r ):
i
–
0.5955, 0.4769, 0.4196, 0.9173, 0.5176, –0.7444.
≠
1. Kaczorowska, K., Kolarska, Z., Mitka, K., and Kowal-
ski, P., Tetrahedron, 2005, vol. 61, p. 8315.
https://doi.org/10.1016/tet2005.05044
logΔG = 1.8668 – (0.1698±0.0485)f(n) – (0.0468±0.0115)f(ε)
–
2
(0.0000±0.0000)B + (0.0018±0.0003)E – (0.0001±0.0000)δ
T
–
(0.0002±0.0001)VM;
(18)
2
3
4
5
6
7
. Petzold, H., Bräutigam, S., and Görls, H., Inorg. Chim.
Acta, 2004, vol. 357, no. 6, p. 1897.
https://doi.org/10.1016/j.ica.200312.004
N = 12, R = 0.9860, S = 0.0020, F = 16.5837.
2
≠
The terms V , δ , and B almost do not affect the ΔG
value. Exclusion of these terms gave three-parameter
correlation (19) with a lightly lower value of R (0.9517);
M
. Sato, K., Hyodo, M., Aoki, M., and Xiao-Qi, Z., Tetra-
hedron, 2001, vol. 57, no. 13, p. 2469.
https://doi.org/10.1016/S0040-4020(01)00068-0
≠
2
logΔG = 1.8627 – (0.0333±0.0304)f(n ) – (0.0266±0.0123)f(ε)
(0.0017±0.0002)ET; (19)
N = 12, R = 0.9517, S = 0.0028, F = 1177.1582.
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shem, M., Catal. Commun., 2014, vol. 52, no. 5, p. 16.
https://doi.org/10.1016/j.catcom.2014.03.026
+
Thus, the main factors affecting the oxidation of
dimethyl sulfoxide with peroxydecanoic acid in different
solvents are specific and nonspecific solvation of both
reactants and structural factors of the reaction medium.
. Lahti, D.W. and Esperson, J.H., Inorg. Chem., 2000,
vol. 39, no. 10, p. 2164.
https://doi.org/10.1021/ic991292b
. Kaur, N. and Kishore, D., Synth. Commun., 2014,
vol. 44, no. 6, p. 721.
https://doi.org/10.1080/0397911.2012.74669
EXPERIMENTAL
Peroxy acids were synthesized by reacting the
corresponding carboxylic acid with 60% hydrogen
peroxide in concentrated sulfuric acid according to the
procedure described in [26] and were purified by repeated
recrystallization. Samples of peroxy acids containing no
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