Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів
Cyclic voltammetry was applied to a series of substituted bis(2-nitrophenyl)disulfides in acetonitrile containing tetraethylammonium tetrafluoroborate under unified experimental conditions. Seven compounds were initially considered (S01-S07). One of them (S07) proved practically insoluble in acetoni...
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| author | Puskov, Volodymyr O. Lyapunov, Alexander Yu. |
| author_facet | Puskov, Volodymyr O. Lyapunov, Alexander Yu. |
| author_institution_txt_mv | [
{
"author": "Volodymyr O. Puskov",
"institution": "Taras Shevchenko National University of Kyiv; Enamine Ltd"
},
{
"author": "Alexander Yu. Lyapunov",
"institution": "Taras Shevchenko National University of Kyiv; Enamine Scientific Research Institute"
}
] |
| author_sort | Puskov, Volodymyr O. |
| baseUrl_str | https://ophcj.nuph.edu.ua/oai |
| collection | OJS |
| datestamp_date | 2026-06-10T08:24:31Z |
| description | Cyclic voltammetry was applied to a series of substituted bis(2-nitrophenyl)disulfides in acetonitrile containing tetraethylammonium tetrafluoroborate under unified experimental conditions. Seven compounds were initially considered (S01-S07). One of them (S07) proved practically insoluble in acetonitrile and was excluded from further analysis. As a result, the electrochemical study was performed for six compounds (S01–S06). Among them, three compounds had voltammograms suitable for semiquantitative treatment, including the comparison of cathodic peak currents, whereas the remaining three compounds provided only qualitative electrochemical information due to their limited solubility and attenuated current response. The multistage cathodic behavior was observed in all cases suitable for analysis. The comparison with nitrobenzene measured under identical conditions indicated a nitro-related reduction process in the region of approximately –1.1 V vs Ag/AgCl and a stronger cathodic process near –1.7 V, which was consistent with the cleavage of the disulfide bond and might overlap with a deeper nitro-related reduction. Substituent effects were evident both in peak potentials and, for the more soluble subset, in the cathodic current value. The results show that cyclic voltammetry is a useful screening tool for substituted aromatic nitrodisulfides, even when the solubility prevents the uniform quantitative comparison across the whole series. |
| doi_str_mv | 10.24959/ophcj.26.360215 |
| first_indexed | 2026-06-11T01:00:23Z |
| format | Article |
| fulltext |
ISSN 2308-8303 (Print) / 2518-1548 (Online) 21
Technical Note
http://ophcj.nuph.edu.ua
UDC 543.552:547.789
V. O. Puskov1,2, A. Yu. Lyapunov1,3
1 Taras Shevchenko National University of Kyiv, 60 Volodymyrska Str., 01033 Kyiv, Ukraine
2 Enamine Ltd., 78 Winston Churchill Street, 02094 Kyiv, Ukraine
3 Enamine Scientific Research Institute, 67 Winston Churchill str., 02094 Kyiv, Ukraine
Cyclic Voltammetric Profiling of Bis(2-nitrophenyl)Disulfides
in a Benzothiazole Precursor Series
Abstract
Cyclic voltammetry was applied to a series of substituted bis(2-nitrophenyl)disulfides in acetonitrile containing tetraethylam-
monium tetrafluoroborate under unified experimental conditions. Seven compounds were initially considered (S01 – S07).
One of them (S07) proved practically insoluble in acetonitrile and was excluded from further analysis. As a result, the elec-
trochemical study was performed for six compounds (S01 – S06). Among them, three compounds had voltammograms
suitable for semiquantitative treatment, including the comparison of cathodic peak currents, whereas the remaining three
compounds provided only qualitative electrochemical information due to their limited solubility and attenuated current re-
sponse. The multistage cathodic behavior was observed in all cases suitable for analysis. The comparison with nitrobenzene
measured under identical conditions indicated a nitro-related reduction process in the region of approximately –1.1 V vs Ag/
AgCl and a stronger cathodic process near –1.7 V, which was consistent with the cleavage of the disulfide bond and might
overlap with a deeper nitro-related reduction. Substituent effects were evident both in peak potentials and, for the more
soluble subset, in the cathodic current value. The results show that cyclic voltammetry is a useful screening tool for substitut-
ed aromatic nitrodisulfides, even when the solubility prevents the uniform quantitative comparison across the whole series.
Keywords: cyclic voltammetry; aromatic disulfides; nitroarenes; benzothiazoles; redox properties; substituent effects
В. О. Пуськов1,2, А. Ю. Ляпунов1,3
1 Київський національний університет імені Тараса Шевченка, вул. Володимирська, 60, м. Київ, 01033,
Україна
2 ТОВ НВП «Єнамін», вул. Вінстона Черчилля, 78, м. Київ, 02094, Україна
3 НУ НДІ «Єнамін», вул. Вінстона Черчилля, 67, м. Київ, 02094, Україна
Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів
Анотація
Циклічну вольтамперометрію застосовували для дослідження серії заміщених біс(2-нітрофеніл)дисульфідів в ацетоні-
трилі з додаванням тетраетиламоній тетрафлуороборату. Вимірювання здійснювали в уніфікованих експерименталь-
них умовах. Було розглянуто 7 сполук (S01 – S07), одна з яких (S07) виявилася практично нерозчинною в ацетонітрилі,
тому її було виключено з подальшого аналізу. У результаті електрохімічне дослідження виконували для шести сполук
(S01 – S06). Для трьох із них отримали вольтамперограми, придатні для напівкількісної обробки, зокрема для по-
рівняння катодних пікових струмів. Інші три сполуки через обмежену розчинність і слабший струмовий відгук дали
лише якісну електрохімічну інформацію. У всіх випадках, придатних для аналізу, спостерігали багатостадійну катодну
поведінку. Порівняння з нітробензеном, виміряним у тих самих умовах, дозволило віднести процес у ділянці близько
–1,1 В щодо Ag/AgCl до відновлення нітрогрупи. Більш інтенсивний катодний процес поблизу –1,7 В узгоджується з
розщепленням дисульфідного зв’язку, хоча він також може частково перекриватися з глибшим відновленням нітро-
групи. Вплив замісників проявлявся як у зміні пікових потенціалів, так і, для краще розчинних сполук, у величині
катодного струму. Отримані результати свідчать, що циклічна вольтамперометрія є корисним методом первинного
електрохімічного скринінгу заміщених ароматичних нітродисульфідів навіть тоді, коли обмежена розчинність не до-
зволяє виконати повноцінне кількісне порівняння для всієї серії.
Ключові слова: циклічна вольтамперометрія; ароматичні дисульфіди; нітроарени; бензотіазоли; редокс-властивості;
вплив замісників
ISSN 2308-8303 (Print) / 2518-1548 (Online) 22
Журнал органічної та фармацевтичної хімії 2026, 24 (2)
Citation: Puskov, V. O.; Lyapunov, A. Yu. Cyclic Voltammetric Profiling of Bis(2-nitrophenyl)Disulfides in a Benzothiazole Precursor Series.
Journal of Organic and Pharmaceutical Chemistry 2026, 24 (2), 21 – 26.
https://doi.org/10.24959/ophcj.26.360215
Received: 10 February 2026; Revised: 16 April 2026; Accepted: 21 April 2026
Copyright© 2026, V. O. Puskov, A. Yu. Lyapunov. This is an open access article under the CC BY license
(http://creativecommons.org/licenses/by/4.0).
Supporting information: Row data in the *.OPJ format.
Funding: The work was funded by the National Academy of Sciences of Ukraine (Grant No. 0119U102718).
Conflict of interests: The authors have no conflict of interests to declare.
■ Introduction
Aromatic nitro compounds and aromatic di-
sulfides represent two important classes of redox-
active organic molecules. Their cathodic behavior
is often multistage and may involve coupled elec-
tron-transfer and chemical steps, which makes
cyclic voltammetry a useful tool for comparing
the effect of the structure and substituents on re-
duction pathways [1 – 3]. Nitroarenes are known
to display complex reduction profiles in aprotic
media, whereas aromatic disulfides may under-
go characteristic bond-cleavage processes after
electron uptake [2 – 5].
Substituted bis(2-nitrophenyl)disulfides com-
bine both of these electroactive motifs in one mo-
lecule. For such systems, the cyclic voltammet-
ric analysis is potentially informative in at least
three aspects: first, it allows the comparison of
reduction potentials within a structurally re-
lated series; second, it provides a simple way to
distinguish qualitatively between nitro-related and
disulfide-related cathodic processes; and third, it
helps to reveal practical limitations, such as in-
sufficient solubility in the aprotic medium, that
may strongly affect the electrochemical response.
In our previous work [2], we proposed a scal-
able single-step procedure for producing 2-alkyl-
substituted benzothiazoles from the correspond-
ing bis(2-nitrophenyl)disulfides (Scheme 1).
The reaction conditions were carefully optimized
with respect to reducing agents (diverse sodium
salts), solvents, ratios, and reaction time. While
optimizing, we noted that the reducing agent
played a crucial role in the reaction efficiency.
Against this background, cyclic voltammetric
profiling of the bis(2-nitrophenyl)disulfides from
the above benzothiazole platform appears a nat-
ural next step. Therefore, in the present commu-
nication, a set of substituted bis(2-nitrophenyl)
disulfides was examined by cyclic voltammetry
in acetonitrile under unified conditions. The aim
NO2
S
R
O2N
S
R
R1CO2H
Na2SO3, Na2S2O3
or Na2S2O4
R
S
N
R1 Up to 350 g
in a single run
R1 = H, Me, Et
CF3, CO2Me, CO2H
+
2 3 1
S
N
R1
R
3NO2
S
O2N
S
R
R1
R
R2
R Na2S2O3
Na2S2O4
Na2SO3
reduction ability
RedOx
process
A
Na2S2O3
Na2S2O4
Na2SO3
H
SO2
NH2
SH
R
R
B
R1 OH
O
R3
O
O-
O- S+
O
Acid activation
C
via
R1 O
O
S
OH
O
Heterocyclization
D
6
7 ( )tentative structure
1
78 90 %–
Scheme 1. The “direct” synthesis of benzothiazoles 1 from acids 2 and bis(2-nitrophenyl)disulfides 3 promoted by sulfur oxo salts,
with the preliminary mechanistic explanation
ISSN 2308-8303 (Print) / 2518-1548 (Online) 23
Journal of Organic and Pharmaceutical Chemistry 2026, 24 (2)
of the work was to evaluate the effect of substi-
tuents on the voltammetric profile of this class
of compounds and determine which conclusions
can be drawn quantitatively and which can only
be drawn qualitatively because of solubility lim-
itations.
■ Materials and methods
Materials
The substituted bis(2-nitrophenyl)disulfides
S01 – S07 were used as the analytes in the present
study (Figure 1). The compounds were available
from the previous synthetic work or prepared as
described in the work [5]. Acetonitrile of electro-
chemical grade (stated purity 99.993 %) was used
as a solvent. Tetraethylammonium tetrafluoro-
borate was used as a supporting electrolyte at
0.1 mol L–1. Nitrobenzene was used as a reference
substrate. Ferrocene was used as a calibration
standard [6].
Cyclic voltammetry
Cyclic voltammetric measurements were car-
ried out on an Elins P-8S potentiostat in a three-
electrode cell at 18 °C. The working electrode
was a Metrohm glassy-carbon electrode, 2.0 mm
in diameter. A glassy-carbon rod (2 mm diame-
ter, immersed to ca. 2 cm) was used as a counter
electrode. The reference electrode was Ag/AgCl
(3 mol L–1 KCl) connected through a 3 mol L–1
KCl aqueous bridge. Potentials in the present
paper are reported versus Ag/AgCl.
The nominal concentration of each analyte was
5 × 10–3 mol L–1. However, for partially soluble
compounds, the effective concentration was lower
than the nominal value. Prior to the measure-
ments, the solutions were degassed with argon
(99.99 %). The scan rate was 100 mV s–1. The blank
electrolyte and nitrobenzene were recorded un-
der the same experimental conditions as the ana-
lytes. Repeated scans were performed on the
same solution.
The instrumental potential window of the
system allowed scanning approximately from
-2.7 to +2.3 V, while the practically reliable
range was approximately -2.5 to +2.0 V. The fer-
rocene calibration was performed under the same
reference-electrode conditions.
■ Results and discussion
The structures of the compounds examined
are given in Figure 1. Seven substituted bis(2-ni-
trophenyl)disulfides S01 – S07 were initially se-
lected for the cyclic voltammetric analysis in ace-
tonitrile. One compound, S07, exhibited only
a very weak electrochemical response due to the
practically complete insolubility under the condi-
tions used and was therefore excluded from fur-
ther discussion. The remaining six compounds,
S01 – S06, yielded analyzable electrochemical data,
but the quality of the information obtained was
not uniform.
For three compounds, the voltammograms were
of sufficient quality to permit the semiquantita-
tive comparison, including the comparison of ca-
thodic peak currents. For the other three com-
pounds, the current response was too strongly li-
mited by the incomplete dissolution to allow the
meaningful current-based comparison; however,
the peak positions and overall voltammetric sha-
pe still provided the qualitative electrochemical
information. Accordingly, the discussion below
is divided into two levels: a semiquantitative
interpretation for the more soluble subset and
a qualitative interpretation for the limited-sol-
ubility subset.
Since no mixed-solvent system was explored,
the present paper treats the difference in solu-
bility not as an optimization problem, but as an
intrinsic experimental limitation of the dataset.
For this reason, absolute peak currents are dis-
cussed only for the more soluble subset, whereas
for the limited-solubility subset, the interpreta-
tion is restricted to cathodic peak potentials and
general voltammetric features.
The voltammetric profiles of all compounds
analyzed differ clearly from those of the blank
NO2
S
O2N
S
NO2
S
O2N
S
Me
Me
NO2
S
O2N
S
NO2
S
O2N
S
NO2
S
O2N
S
MeS
SMe
NO2
S
O2N
S
S01 S02
Br
Br
S03
S04 S05 S06
Me
Me
Me
Me
MeO
OMe
NO2
S
O2N
S
S07
MeO2C
CO2Me
Figure 1. Structures of substituted bis(2-nitrophenyl)disulfides S01 – S07 investigated in the present study
ISSN 2308-8303 (Print) / 2518-1548 (Online) 24
Журнал органічної та фармацевтичної хімії 2026, 24 (2)
electrolyte and nitrobenzene recorded under iden-
tical conditions (for more details, see SI files).
In each case, more than one cathodic process is
observed, indicating that the reduction of substi-
tuted bis(2-nitrophenyl)disulfides in aprotic me-
dia is a multistage rather than a simple one-wave
process. For the more soluble subset (Figure 2),
both cathodic peak potentials and peak-current va-
lues can be compared semiquantitatively. For the
limited-solubility subset (Figure 3), only the posi-
tions of the main cathodic processes and their re-
lative shifts can be interpreted with confidence.
The full voltammetric overlays for the infor-
mative compounds are shown in Figure 2. In all
three cases, the analyte traces clearly differ from
the blank background and from nitrobenzene re-
corded under identical conditions. The analytes
display multistage cathodic responses and lack
the simple matched anodic return waves, con-
sistent with the chemically coupled, overall irre-
versible behavior rather than a single reversible
one-electron process [3 – 5].
The comparison with nitrobenzene is useful
for determining the main cathodic processes.
Under the present conditions, nitrobenzene ex-
hibits principal cathodic features at approxi-
mately –1.16 and –1.91 V versus Ag/AgCl. In the
disulfide series, the cathodic process observed
near –1.1 V, with a substituent-dependent shift
of several tenths of a volt, is reasonably asso-
ciated with the reduction of the nitro group.
In contrast, the more intense process centered
near –1.7 V is consistent with the cleavage of the
disulfide bond and may overlap with a deeper
nitro-related reduction step. Since no non-nitro
disulfide control has not been measured, this
assignment is best regarded as well-supported
rather than definitive.
A clear substituent effect is observed across
the series. Depending on the substituent pattern,
the nitro-related cathodic process shifts either to
more negative or to less negative potential rela-
tive to nitrobenzene. For the more soluble sub-
set, this effect is accompanied by substantial
Figure 2. Cyclic voltammograms of the three compounds (S01, S04, S06) affording semiquantitative electrochemical data and that
of nitrobenzene in MeCN / 0.1 mol L–1 Et4NBF4 at 100 mV s–1 and 18 °C on a glassy-carbon working electrode versus Ag/AgCl.
For each analyte, the corresponding blank electrolyte recorded under identical conditions is overlaid
ISSN 2308-8303 (Print) / 2518-1548 (Online) 25
Journal of Organic and Pharmaceutical Chemistry 2026, 24 (2)
differences in the cathodic peak-current value,
which indicates that the substituent variation
affects not only the reduction potential, but also
the practical electrochemical response observed
under identical concentration and instrumental
conditions. For the limited-solubility subset, the
same trend can still be discussed qualitatively
on the basis of peak positions although current
values are no longer suitable for comparison.
Thus, the six compounds analyzed should be
treated as two subsets: S01, S04, and S06, which
gave semiquantitative electrochemical data, and
S02, S03, and S05, which afforded only qualitative
electrochemical information, whereas S07 was ex-
cluded because of the practical insolubility in MeCN.
Repeated scans performed on the same solu-
tion showed that the principal cathodic features
remained recognizable although changes in the
current profile and the return-wave region were
observed. This behavior is consistent with a mul-
tistage electrode process involving the electron
transfer followed by the chemical transformation
and/or adsorption effects on the electrode surface.
Since the main purpose of the present communi-
cation is a comparative profiling of the compound
series rather than a detailed kinetic analysis,
these repeat-scan effects are noted here only as
supporting evidence that the recorded cathodic
processes are real and reproducible within the
same solution.
For convenience, the key electrochemical ob-
servations are summarized in Table 1. Due to
the concentration uncertainty resulting from the
incomplete solubility, the table is limited to quali-
tative or semiquantitative descriptors rather than
kinetic or mechanistic parameters.
Taken together, these data do not establish
a complete electroreduction mechanism for sub-
stituted bis(2-nitrophenyl)disulfides in the apro-
tic medium. They do, however, show that the
compounds analyzed do not behave as simple
one-wave nitroarenes. Instead, the voltammo-
grams are consistent with at least two chemical-
ly distinct cathodic processes: a substituent-
dependent nitro-related reduction in the region
near –1.1 V and a stronger process near –1.7 V
Figure 3. Cyclic voltammograms of the three compounds affording only qualitative electrochemical data under the same conditions as
in Figure 2. Because of the limited solubility in MeCN, these voltammograms are discussed in terms of cathodic peak positions and the
overall profile rather than the peak-current value
ISSN 2308-8303 (Print) / 2518-1548 (Online) 26
Журнал органічної та фармацевтичної хімії 2026, 24 (2)
that is consistent with the disulfide bond cleav-
age and overlaps with a deeper nitro-related re-
duction. The work also shows that the solubility
in MeCN is not a minor experimental inconven-
ience, but a major variable determining wheth-
er the given member of the series can be treated
quantitatively or only qualitatively.
■ Conclusions
A cyclic voltammetric study of seven substi-
tuted bis(2-nitrophenyl)disulfides in acetonitrile
has been performed under unified aprotic condi-
tions. One compound, S07, proved practically in-
soluble in MeCN and was excluded from the elec-
trochemical interpretation. The remaining six com-
pounds, S01 – S06, yielded analyzable data, but at
two different levels of reliability: three compounds
gave semiquantitative voltammograms suitable
for the comparison of both peak potentials and
peak-current values, whereas three compounds
provided only qualitative electrochemical infor-
mation because of their limited solubility.
In all the cases analyzed, the multistage ca-
thodic behavior was observed. The comparison
with nitrobenzene measured under identical con-
ditions supports the assignment of the process
near –1.1 V to the nitro-group reduction, while
the stronger process near –1.7 V is consistent
with the disulfide bond cleavage, possibly over-
lapping with a deeper nitro-related reduction.
A clear substituent effect was observed across
the series, manifested as shifts in cathodic peak
potentials and, for the more soluble subset, dif-
ferences in the peak-current value.
Thus, cyclic voltammetry is shown to be a use-
ful comparative method for substituted bis(2-nit-
rophenyl)disulfides. At the same time, the study
demonstrates that solubility in the aprotic me-
dium is a decisive practical factor that limits the
uniform quantitative comparison within the se-
ries of these compound.
■ References
1. Henary, M.; Paranjpe, S.; Owens, E. A. Synthesis and applications of benzothiazole-containing cyanine dyes. Heterocycl. Commun.
2013, 19, 1 – 11. https://doi.org/10.1515/hc-2013-0012.
2. Puskov, V. O.; Babii, S. B.; Adamenko, I. V.; Melnychuk, S. O.; Druzhenko, T. V.; Lyapunov, A. Y.; Popov, S. V.; Volochnyuk, D. M.; Rya-
bukhin, S. V. Practical one-pot synthesis of 2-alkyl-substituted benzothiazoles from bis-(2-nitrophenyl)-disulfides. Org. Process Res.
Dev. 2024, 28, 4273 – 4280. https://doi.org/10.1021/acs.oprd.4c00136.
3. Orlandi, M.; Brenna, D.; Harms, R.; Jost, S.; Benaglia, M. Recent developments in the reduction of aromatic and aliphatic nitro com-
pounds to amines. Org. Process Res. Dev. 2018, 22, 430 – 445. https://doi.org/10.1021/acs.oprd.6b00205.
4. Huang, Y.; Lessard, J. Electrochemical behaviour of nitrobenzene, nitrosobenzene, azobenzene, and azoxybenzene on Hg, Pt, Cu, and
Ni electrodes in aprotic medium. Electroanalysis 2016, 28, 2716 – 2727. https://doi.org/10.1002/elan.201600216.
5. Antonello, S.; Daasbjerg, K.; Jensen, H.; Taddei, F.; Maran, F. Formation and cleavage of aromatic disulfide radical anions. J. Am. Chem.
Soc. 2003, 125, 14905 – 14916. https://doi.org/10.1021/ja036380g.
6. Gagné, R. R.; Koval, C. A.; Lisensky, G. C. Ferrocene as an internal standard for electrochemical measurements. Inorg. Chem. 1980, 19,
2854 – 2855. https://doi.org/10.1021/ic50211a080.
Information about the authors:
Volodymyr O. Puskov, Ph.D. student of the Institute of High Technologies, Taras Shevchenko National University of Kyiv;
Chemist, Enamine Ltd.
Alexander Yu. Lyapunov (corresponding author), Ph.D. in Chemistry, Senior Researcher of the Institute of High Technologies,
Taras Shevchenko National University of Kyiv; Senior Researcher of the Enamine Scientific Research Institute;
https://orcid.org/0000-0002-7538-303X; e-mail for correspondence: alexander.yu.lyapunov@gmail.com.
Table 1. Electrochemical characteristics of the substituted bis(2-nitrophenyl)disulfides studied in MeCN
Compound Structural feature Data level used
in the discussion
Current-based
comparison
Screening
current, µA Comment
S01 unsubstituted semiquantitative yes 150 suitable for the comparison
of potentials and currents
S02 dimethyl-substituted qualitative no 100 discussion restricted to potentials
and the voltammetric shape
S03 polymethyl-substituted qualitative no 60 discussion restricted to potentials
and the voltammetric shape
S04 dibromo-substituted semiquantitative yes 180 suitable for the comparison of
potentials and currents
S05 bis(methylthio)-
substituted qualitative no 120 limited-solubility dataset
S06 dimethoxy-substituted semiquantitative yes 200 highest current response among
the compounds analyzed
S07 ester-substituted excluded no 20 practically insoluble in MeCN
|
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| institution | Journal of Organic and Pharmaceutical Chemistry |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-06-11T01:00:23Z |
| publishDate | 2026 |
| publisher | National University of Pharmacy |
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| resource_txt_mv | ophcjnupheduua/55/a1ae1878ba188333bd73f5d44be9db55.pdf |
| spelling | oai:ojs.journals.uran.ua:article-3602152026-06-10T08:24:31Z Cyclic Voltammetric Profiling of Bis(2-nitrophenyl)Disulfides in a Benzothiazole Precursor Series Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів Puskov, Volodymyr O. Lyapunov, Alexander Yu. циклічна вольтамперометрія ароматичні дисульфіди нітроарени бензотіазоли редокс-властивості вплив замісників cyclic voltammetry aromatic disulfides nitroarenes benzothiazoles redox properties substituent effects Cyclic voltammetry was applied to a series of substituted bis(2-nitrophenyl)disulfides in acetonitrile containing tetraethylammonium tetrafluoroborate under unified experimental conditions. Seven compounds were initially considered (S01-S07). One of them (S07) proved practically insoluble in acetonitrile and was excluded from further analysis. As a result, the electrochemical study was performed for six compounds (S01–S06). Among them, three compounds had voltammograms suitable for semiquantitative treatment, including the comparison of cathodic peak currents, whereas the remaining three compounds provided only qualitative electrochemical information due to their limited solubility and attenuated current response. The multistage cathodic behavior was observed in all cases suitable for analysis. The comparison with nitrobenzene measured under identical conditions indicated a nitro-related reduction process in the region of approximately –1.1 V vs Ag/AgCl and a stronger cathodic process near –1.7 V, which was consistent with the cleavage of the disulfide bond and might overlap with a deeper nitro-related reduction. Substituent effects were evident both in peak potentials and, for the more soluble subset, in the cathodic current value. The results show that cyclic voltammetry is a useful screening tool for substituted aromatic nitrodisulfides, even when the solubility prevents the uniform quantitative comparison across the whole series. Циклічну вольтамперометрію застосовували для дослідження серії заміщених біс(2-нітрофеніл)дисульфідів в ацетонітрилі з додаванням тетраетиламоній тетрафлуороборату. Вимірювання здійснювали в уніфікованих експериментальних умовах. Було розглянуто 7 сполук (S01–S07), одна з яких (S07) виявилася практично нерозчинною в ацетонітрилі, тому її було виключено з подальшого аналізу. У результаті електрохімічне дослідження виконували для шести сполук (S01–S06). Для трьох із них отримали вольтамперограми, придатні для напівкількісної обробки, зокрема для порівняння катодних пікових струмів. Інші три сполуки через обмежену розчинність і слабший струмовий відгук дали лише якісну електрохімічну інформацію. У всіх випадках, придатних для аналізу, спостерігали багатостадійну катодну поведінку. Порівняння з нітробензеном, виміряним у тих самих умовах, дозволило віднести процес у ділянці близько –1,1 В щодо Ag/AgCl до відновлення нітрогрупи. Більш інтенсивний катодний процес поблизу –1,7 В узгоджується з розщепленням дисульфідного зв’язку, хоча він також може частково перекриватися з глибшим відновленням нітрогрупи. Вплив замісників проявлявся як у зміні пікових потенціалів, так і, для краще розчинних сполук, у величині катодного струму. Отримані результати свідчать, що циклічна вольтамперометрія є корисним методом первинного електрохімічного скринінгу заміщених ароматичних нітродисульфідів навіть тоді, коли обмежена розчинність не дозволяє виконати повноцінне кількісне порівняння для всієї серії. National University of Pharmacy 2026-06-10 Article Article Peer-reviewed Article application/pdf application/x-7z-compressed https://ophcj.nuph.edu.ua/article/view/360215 10.24959/ophcj.26.360215 Journal of Organic and Pharmaceutical Chemistry; Vol. 24 No. 2 (2026): Issue in Progress; 21-26 Журнал органической и фармацевтической химии; Том 24 № 2 (2026): Issue in Progress; 21-26 Журнал органічної та фармацевтичної хімії; Том 24 № 2 (2026): Issue in Progress; 21-26 2518-1548 2308-8303 en https://ophcj.nuph.edu.ua/article/view/360215/349946 https://ophcj.nuph.edu.ua/article/view/360215/349947 Copyright (c) 2026 National University of Pharmacy http://creativecommons.org/licenses/by/4.0 |
| spellingShingle | циклічна вольтамперометрія ароматичні дисульфіди нітроарени бензотіазоли редокс-властивості вплив замісників Puskov, Volodymyr O. Lyapunov, Alexander Yu. Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| title | Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| title_alt | Cyclic Voltammetric Profiling of Bis(2-nitrophenyl)Disulfides in a Benzothiazole Precursor Series |
| title_full | Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| title_fullStr | Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| title_full_unstemmed | Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| title_short | Циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| title_sort | циклічна вольтамперометрія біс(2-нітрофеніл)дисульфідів – попередників бензотіазолів |
| topic | циклічна вольтамперометрія ароматичні дисульфіди нітроарени бензотіазоли редокс-властивості вплив замісників |
| topic_facet | циклічна вольтамперометрія ароматичні дисульфіди нітроарени бензотіазоли редокс-властивості вплив замісників cyclic voltammetry aromatic disulfides nitroarenes benzothiazoles redox properties substituent effects |
| url | https://ophcj.nuph.edu.ua/article/view/360215 |
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