Structure, Anticorrosion and Antibacterial Evaluation of (E)-3-(N-Oxide-methylimino)indolin-2-one

Article abstract of DOI:10.1134/S107042721805004X

A nitrone, (E)-3-(N-oxide-methylimino)indolin-2-one, was synthesized and analyzed by X-ray single crystal analysis. The inhibition and the mechanism of action of the title compound on the corrosion of high protective Q235A steel in HCl solution were scree

Full text of DOI:10.1134/S107042721805004X

ISSN 1070-4272, Russian Journal of Applied Chemistry, 2018, Vol. 91, No. 5, pp. 750−757. © Pleiades Publishing, Ltd., 2018.
ORGANIC SYNTHESIS AND INDUSTRIAL
ORGANIC CHEMISTRY
Structure, Anticorrosion and Antibacterial Evaluation
of (E)-3-(N-Oxide-methylimino)indolin-2-one1
Li Baia, Lajun Fenga, Jiao Yanb, Jiao Linb, Jie Zhangb,
Yun Mab, Xuefan Gub, and Gang Chenb,*
a School of Materials Science and Engineering, Xi’an University of Technology, Xi’an 710048, China
b College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an, 710065, China
*e-mail: gangchen@xsyu.edu.cn
Received February 27, 2018
Abstract—A nitrone, (E)-3-(N-oxide-methylimino)indolin-2-one, was synthesized and analyzed by X-ray single
crystal analysis. The inhibition and the mechanism of action of the title compound on the corrosion of high protective
Q235A steel in HCl solution were screened and discussed by weight loss and electrochemical measurements. The
mechanism of action of (E)-3-(N-oxide-methylimino)indolin-2-one in HCl solution was screened for the corrosion
of N80 steel in 1-methylindolin-2-one solution, and the inhibition mechanism was discussed. The results indicated
that it can inhibit the corrosion with moderate inhibition efficiency in different conditions, and the mechanism of the
corrosion inhibiting may be mainly contributed to the adsorption. It was screened for antibacterial activity against
oilfield water-borne bacteria, and it showed good to moderate activity against sulfate reducing bacteria.
DOI: 10.1134/S107042721805004X
INTRODUCTION
antibacterial activity against Bacillus subtilis, Gram(+)
and Gram(−) bacterial strains and Magnaporthe grisea
[5, 6] among others.
Nitron is mainly used in organic chemistry. The
importance of the nitrone functionality has been revealed
by the growing number of scientific papers which
appeared in the literature over the last years concerning
nitrones and related compounds. Nitrones are easily
prepared by several methods well-documented in the
primary literature. The methods most used includes
condensation reactions between carbonyl compounds and
oxidation of amines, imines or hydroxylamines.
It was found that electrical functional group and p
and/or π-electron in triple or conjugated double bond-
containing compound is effective against negative metal
corrosion inhibitors [7, 8]. It was widely recognized that
organic inhibitors act by transferring p and/or π-electrons
from metals and organic compounds in the formation of
chemisorption coordinate covalent bond typically on a
metal surface to promote the formation of complexes
[9‒11]. Organic compounds produced in condensation of
an amine and a ketone/aldehyde ( Schiff bases) containing
hetero atoms (sulfur, phosphorus, nitrogen, and oxygen),
aromatic ring which are the main adsorption centers,
are such typical molecules [12‒14]. Some polydentate
Schiff base compounds (PSCs) have been confirmed as
effective corrosion inhibitors for various metals in acid
media [13, 15‒17]. Several isatin derivatives have been
confirmed as inhibitors in HCl solution [18‒20]. The aim
of this work is to screen the inhibition of a nitrone, (E)-
3-(N-oxide-methylimino)indolin-2-one, for the corrosion
Isatin, 1H-indole-2,3-dione, is an important indole
derivative, which was first obtained by Erdmann and
Laurent in 1841 as a product from the oxidation of indigo
dye by nitric acid and chromic acids. The compound
is present in many plants, such as Isatis tinctoria,
Calanthe discolor, Strobilanthes cusia (Nees) Kuntze,
and Couroupita guianensis Aubl., even in mammalian
tissue [1, 2]. It has versatile bioactivity, which is useful
to synthesize a large variety of heterocyclic compounds
in preparing drugs [3, 4]. Schiff bases of isatin have
1 The text was submitted by the authors in English.
750

STRUCTURE, ANTICORROSION AND ANTIBACTERIAL EVALUATION
751
Scheme 1. Synthesis of (E)-3-(N-oxide-methylimino)indolin-2-one.
X-ray data collection and structure refinement.
Intensity data for colorless crystals of compound was col-
lected at 150 K on a Bruker SMART 1000 CCD fitted with
MoKα radiation. The data sets were corrected for absorption
based on multiple scansand reduced using standard meth-
ods. The structures was solved by direct-methods [13] and
refined by a full-matrix least squares procedure on F2 with
anisotropic displacement parameters for non-hydrogen
atoms, carbon- and nitrogen bound hydrogen atoms in their
calculated positions and a weighting scheme of the form
w = 1/[σ2(Fo ) + (αP)2 + bP], where P = (Fo + 2Fc2)/3).
All hydrogen atoms were positioned geometrically and al-
lowed to ride on their parent atoms, with d(N‒H) = 0.86 Å
and Uiso(H) = 1.2 Ueq(N), d(C‒H) = 0.93 or 0.96 (CH3) Å
and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C). Crystal data and
refinement details were given in Table 1.
of mild steel both in high concentrated HCl solution and
microbiologically influenced corrosion.
EXPERIMENTAL
Synthesis of (E)-3-(N-oxide-methylimino)indolin-
2-one(E)-3-(N-oxide-methylimino)indolin-2-one was
performed according to published methods (Scheme 1)
[21, 22]. Isatin (1 mmol) was dissolved in methanol
(20 mL), 10 mLmethanol solution of 1.2 mmol N-methyl-
hydroxylamine was added dropwise. The mixture
was refluxed for 1 h, until disappearance of isatin, as
evidenced by thin-layer chromatography. The solvent
was removed in vacuo and the residue was separated
by column chromatography (silica gel, petroleum ether/
ethyl acetate = 1 : 1 v/v), to give the title compound.
Natural evaporation gave yellow single crystals of the title
compound suitable for X-ray analysis over a period of 4d.
2
2
Gravimetric measurements. The corrosion tests
were performed on Q235Awith a composition (in wt %):
Table 1. Experimental Data of (E)-3-(N-oxide-methylimino)indolin-2-one
Crystal parameter Data Crystal parameter
a, Å 6.951(6) Index ranges
Data
‒4 ≤ h ≤ 5;
‒13 ≤ k ≤ 12;
‒11 ≤ l ≤ 12
b, Å
8.029(7)
8.658(6)
103.00(2)
98.46(2)
115.40(1)
408.67(514)
2
Reflections collected
3112
c, Å
Independent reflections
Reflections theta (deg)
2190
α, °
2.26 to 28.27
0.9440 to 0.9861
1427
β, °
Absorption correction transmission
Reflections with [I > 2σ(I)]
Number of parameters
γ, °
Volume
109
Z
Goodness-of-fit on F2
1.006
Density, mg m‒3
1.510
Final R indices [I > 2σ(I)]
R1 = 0.1884;
wR2 = 0.1323
Absorption coefficient
0.112
R indices (all data)
R1 = 0.0674;
wR2 = 0.1027
F (000)
168
Refine different density
‒0.224 to 0.176
Crystal size, mm3
0.20×0.22×0.30
Theta range for data collection, deg
1.9 to 27.3
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LI BAI et al.
solution. Electrochemical measurements were conducted
in a conventional three-electrode thermostated cell. The
electrode was inserted into a Teflon tube and isolated
with polyester so that only its section (0.5 cm2) was
allowed to contact the aggressive solutions. A platinum
disk as counter electrode and standard calomel electrode
(SCE) as the reference electrode have been used in the
electrochemical studies.
The potentiodynamic curves were recorded using a
CS350 system connected to a personal computer. The
working electrode was first immersed in the test solution
for 60 min to establish a steady state open circuit potential.
After measuring the open circuit, potential dynamic
polarization curves were obtained with a scan rate of
0.5 mV s‒1. Corrosion rates (corrosion current densities)
were obtained from the polarization curves by linear
extrapolation of the anodic and cathodic branches of the
Tafel plots at points 100 mV more positive and more
Fig. 1. Molecular structure of (E)-3-(N-oxide-methylimino)-
indolin-2-one.
C 0.22, P0.045, Si 0.35, S 0.05, Mn 1.40, and Fe balance.
The electrolyte solution was 2 M HCl, prepared from
analytical grade 38% HCl and distilled water. The
concentration range of 3-(4-hydroxyphenylimino)indolin-
2-one was employed as 100 and 1000 mg L‒1. All tests
have been performed in deaerated solutions and at 60 ±
0.5°C. The gravimetric tests were carried out according
to the People’s Republic of China Standard of Petroleum
and Natural Gas Industry (Evaluation method for behavior
of corrosion inhibitor for produced water of oilfield,
SY/T5273-2000) with a few modifications. Each test
was done with three specimens at the same time to give
reproducible results.
negative than the Ecorr
.
Scanning electron microscopy (SEM). The surface
morphology of the sample under study in the absence and
presence of inhibitors was investigated using a Digital
Microscope Imaging scanning electron microscope
(model SU6600, serial no. HI-2102-0003) at accelerating
voltage of 20.0 kV. Samples were attached on the top of
an aluminum stopper by means of carbon conductive
adhesive tape. All micrographs of the specimen were
taken at 5009 magnification.
Electrochemical measurements. The electrodes were
mechanically abraded with a series of emery papers (800
and 1200 grades), then rinsed in acetone and double-
distilled water before their immersion in the experimental
Microbiological monitoring. Viable counts of SRB,
TGB and FB were determined with the “most probable
Table 2. The atomic coordinates (in Å2) of (E)-3-(N-oxide-methylimino)indolin-2-one
Atom
O1
x/a
y/b
z/c
Atom
C9
x/a
y/b
0.7446(5)
0.69720
0.83160
0.81270
0.4288(5)
0.49000
0.1333(5)
-0.00200
0.2258(5)
0.15070
z/c
0.5293(4)
0.2534(4)
0.3609(4)
0.39390
0.9571(3)
0.4094(3)
0.7373(4)
0.81930
0.7060(3)
0.8098(3)
0.4414(3)
0.38800
0.4723(6)
0.46280
0.41060
0.62480
0.1483(5)
0.16280
0.0100(6)
-0.06740
0.0352(6)
-0.02480
0.9466(4)
1.03920
0.95380
0.94740
0.1986(4)
0.11850
0.2747(5)
0.24220
0.1566(4)
0.04570
O2
H7A
H7B
H7C
C6
N1
H1A
N2
0.3469(4)
0.3293(5)
0.2151(5)
0.2381(5)
0.4224(5)
0.0995(5)
0.08210
0.5782(4)
0.5984(4)
0.4427(4)
0.5349(4)
0.7894(4)
0.2409(5)
0.17900
0.7916(3)
0.6444(4)
0.4873(4)
0.3659(4)
0.6097(4)
0.4423(4)
0.52200
C2
H5A
C4
C8
C7
H3A
C5
C1
C3
H4A
H2A
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STRUCTURE, ANTICORROSION AND ANTIBACTERIAL EVALUATION
753
Table 3. The intermolecular hydrogen bonds parameters of (E)-3-(N-oxide-methylimino)indolin-2-one
D–H···A
D–H
H···A
D···A
D–H···A
N1(i)–H1A(i)···O1(ii)a
0.8593(32)
0.8593(32)
2.033(3)
2.033(3)
2.8845 (46)
2.8845 (46)
170.748(212)
170.748(212)
N1(ii)–H1A(ii)···O1(i)
a Symmetry codes: (i) –x + 1, y + 1/2, –z + 2; (ii) –x + 1, y − 1/2, –z + 2.
number” method, People’s Republic of China Standard
of Petroleum and Natural Gas Industry, the national
method of the bactericidal agent’s performance, SY/T
5890-1993). The produced water containing the three
kinds of bacteria was gathered from Zichang Oilfield
Factory, Yanchang Oilfield.
performance of the title compound as an inhibitor with
the concentration from 100 to 1000 mg L‒1 in 1 M and
2 M HCl under the temperature from 30 to 65°C, and
the results were summarized in Table 4. From the table,
it was found that almost all the inhibition efficiency (IE)
increases along with the concentration of inhibitor, but
there is difference in the two concentrations and different
temperatures, and it reaches to 83.2% with the concentra-
tion of 1000 mg L‒1 in 1M HCl solution, further increase
in the inhibitor concentration does not increase the IE.
RESULTS AND DISCUSSION
Structure. The structural parameters were confirmed
by X-ray analysis from spectroscopic data. Geometric
parameters of (E)-3-(N-oxide-methylimino)indolin-2-
one are in the usual ranges. The atomic coordinates are
displayed inTable 2, and the molecular structure is depicted
in Fig. 1. The space-group is P-1(2) with a triclinic crystal
system. The indol-2-one ring system is substantially
planar, the angle of C2–N2–O2 is 121.359(279)°, and
the angle of C2–N2–C9 is 123.272(262)°. In the crystal
structure, typical intermolecular N–H…O hydrogen
bonds are responsible for the formation of dimmers as
shown in Fig. 2, and the hydrogen bonds parameters
are included in Table 3. The π–π stacking between the
planar moieties is responsible for the formation of a one-
dimensional network, and a packing diagram of (E)-3-(N-
oxide-methylimino)indolin-2-one is depicted in Fig. 3.
Table 4. The corrosion inhibition efficiency of (E)-3-(N-oxide-
methylimino)indolin-2-one
Concentra- HCl con-
Tempera-
ture, °C
Inhibition
efficiency, %
tion,
centra-
tion, M
mg L‒1
100
100
100
100
100
100
200
200
200
200
200
200
500
500
500
500
500
500
1000
1000
1000
1000
1000
1000
1
1
1
2
2
2
1
1
1
2
2
2
1
1
1
2
2
2
1
1
1
2
2
2
30
45
60
30
45
60
30
45
60
30
45
60
30
45
60
30
45
60
30
45
60
30
45
60
15.2
27.8
30.2
18.9
19.8
29.0
29.7
33.2
35.5
21.5
26.9
28.8
45.2
66.3
72.5
44.8
60.0
68.9
68.2
73.1.9
81.5
63.7
69.3
70.4
Inhibitor properties and mechanism. Corrosion is
the chemical reaction of the material (usually metal) with
its environment, and the process of progressive failure of
the material. Corrosion degrades the useful properties of
materials and structures including permeability, appear-
ance and strength to liquids and gases. Thus, corrosion,
which occurs on the exposed surface, is a diffusion con-
trolled process. As a result, the active methods such as
passivation and chromate passivation are used to reduce
the material exposed surfaces, which can increase the
corrosion resistance of the materials. It has been seen that
use of corrosion inhibitors is the most effective method
for the protection against such kind of acid attack. The
inhibitors, such as imidazoline, Mannich base, Schiff
base ,and some other heterocyclic compounds, have been
used in this process, when the concentration or the price
is too high to be accepted. In the following work, the
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LI BAI et al.
Fig. 2. The intermolecular hydrogen bonds of (E)-3-(N-oxide-methylimino)indolin-2-one.
Fig. 3. The packing diagram of (E)-3-(N-oxide-methylimino)indolin-2-one.
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STRUCTURE, ANTICORROSION AND ANTIBACTERIAL EVALUATION
755
Fe2+
Fe2+
Fe2+
Fe2+
Fe2+
Interaction with the p-electrons;
Interaction with the aromatic π-electrons;
Fig. 4. Absorption of (E)-3-(N-oxide-methylimino)indolin-2-one molecules on the ion surface.
Corrosion inhibition mechanism may be mainly
E, V
–0.3
caused by adsorption. The adsorption process is
controlled by the chemical structure of these inhibitors.
The process of adsorption is governed by the chemical
structure of these inhibitors. The presence of N, O, S
atoms and conjugated bonds in the structures makes the
formation of p–d bonds resulting form the overlap of
p electrons to the 3d vacant orbital of Fe atoms, which
conforms the adsorption of the compounds on the metal
surface [23]. The inhibitive performance of (E)-3-(N-
oxide-methylimino)indolin-2-one can be explained by the
presence of polydentate nitrone and indolin which rises
the possibility of transferring the unshared electron of this
molecule to iron [24]. The molecules may absorbed on
the ion surface by the coordinate covalent bonds with the
3d vacant orbital of Fe atoms in the manner described in
Fig. 1 to form the protective film. The possible reaction
centers are unshared electron pair of heteroatoms and/or
p-electrons of aromatic ring. The schematic illustration of
different modes of adsorption on metal is shown in Fig. 4.
Blanc
50 mg L–1
100 mg L–1
200 mg L–1
500 mg L–1
1000 mg L–1
–0.4
–0.5
–0.6
10–8
10–7
10–6
10–5
10–4
10–3
10–2
I, A cm–2
Fig. 5. Typical polarization curves for corrosion of the steel in
2 M HCl in the absence and presence of different concentrations
of (E)-3-(N-oxide-methylimino)indolin-2-one.
indolin-2-one can reduce anodic dissolution and
also retards the hydrogen evolution reaction. With a
concentration of 1 000 mg L–1, the additive exhibits
maximum IE of 80.1%. The extract causes changes in
the anodic, cathodic Tafel slopes and the Ecorr values in
the presence of different concentrations. Ecorr, βa, and
βc values do not change appreciably with the addition
of the inhibitor, which indicates that the inhibitor is not
only interfering with the anodic dissolution or cathodic
hydrogen evolution reactions independently but also acts
Tafel polarisation measurements. The anodic and
cathodic polarization results were shown in Fig. 5. Table 5
shows the electrochemical corrosion kinetic parameters.
As it was expected both anodic and cathodic reactions
of mild steel electrode corrosion were inhibited by the
increase in the title compound concentration. It means
that the addition of the (E)-3-(N-oxide-methylimino)
Table 5. Potentiodynamic polarization parameters for the corrosion of the steel in the 2 M HCl solution containing
(E)-3-(N-oxide-methylimino)indolin-2-one
Concentration, mg L–1 −Ecorr, mV
Icorr, μA cm−2
βc, mV dec−1 Corrosion rate, mm/a
IE, %
βa, mV dec−1
90.435
–
0.4607
0.4647
0.4552
0.4553
0.4609
0.4526
151.445
141.906
90.512
31.432
51.930
30.781
155.21
166.59
146.33
119.67
81.25
1.8022
1.3221
1.0519
0.7986
0.5574
0.35880
–
50
107.112
77.033
26.6
41.6
55.7
69.1
80.1
100
200
500
1,000
63.162
62.719
58.288
135.31
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LI BAI et al.
(a)
(b)
(с)
Fig. 6. SEM micrographs of steel samples after 4 h immersion. (a) Blank; (b) immersion in 2 M HCl, (c) шmmersion in 2 M HCl +
1000 mg L‒1 title compound.
as a mixed-type (anodic/cathodic) of inhibitor. Increasing
IE with increasing concentration of theAE shows that the
inhibition actions are due to its adsorption on the steel
surface [24]. The IEs obtained from potentiodynamic
polarization were quite different from that from weight-
loss measurements, which is due to the fact that the
weight-loss method gives average corrosion rate, whereas
electrochemical method gives instantaneous corrosion
rates.
called microbiologically influenced corrosion (MIC).
It is estimated that 30-50% of the corrosion cases are
a result of microbial activity. MIC caused by growth
of sulfate reducing bacteria (SRB), iron bacteria (IB),
and total general bacteria (TGB) in oil pipelines, is
considered as a major problem for water treatment in the
oil industry. MIC can result in different types of attack:
pitting, crevices, dealloying and erosion in pipelines
[21]. Corrosion products produced by microorganisms
are hydrogen sulfide, molecular hydrogen, hydrogen
ions and metal oxide films destabilized. In addition,
microbial degradation of crude oil can lead to increased
acidity in the oil phase, and oil containing acids is a
problem concerning corrosion of pipelines. The reported
results showed that the interaction of IB, SRB, and
TGB accelerated the corrosion rate, and the corrosion
in the mixture of IB, SRB, and TGB was more serious
than in a single microbial system. If this is the case,
different treatment system should be considered to inhibit
corrosion, among which bactericide agent has received
the greatest acceptance. The antifungal activity of (E)-
3-(N-oxide-methylimino)indolin-2-one against oilfield
microorganism was tested under the concentration of
0.20 and 0.02 g L‒1, and the results were summarized in
Table 6. From the table, it can be found that (E)-3-(N-
oxide-methylimino)indolin-2-one is antifungal active
against SRB and IB, but inactive against TGB under both
concentrations.
Scanning electron microscopy. To evaluate the
conditions of the steel in contact with 2 M HCl acid
solutions, SEM investigation was carried out as shown
in Fig 6. Figures 6a and 6b show the SEM images of
the polished steel sample and of the surface of the steel
specimens after immersion in 2 M HCl solution without
inhibitor for 4 h, respectively. In Fig. 6 there occurs the
result of cracks caused by acidic corrosion attack. The
status in Fig. 6c shows the surface of the steel specimens
immersed for 4 h in 2 M HCl solutions containing
1000 mg L‒1 inhibitor, and the surface appears smooth,
which is much less damaged than that without any
inhibitors. This was due to adsorption of (E)-3-(N-oxide-
methylimino)indolin-2-one on the steel surface, which
accords with the mechanism analysis above.
Bioactivity. Corrosion is an electrochemical process
leading to the deterioration of materials that can be
caused or accelerated by microbiological activity, so
CONCLUSION
Table6.Theantifungalactivityof(E)-3-(N-oxide-methylimino)-
indolin-2-one against oilfield water-borne bacteria
(E)-3-(N-oxide-methylimino)indolin-2-one was
synthesized and its inhibition and action mechanism
on the corrosion of high protective Q235A steel in HCl
solution were investigated by multi-method. It can inhibit
corrosion with moderate inhibition efficiency in different
conditions and the highest IE reaches to 83.2% with
the concentration of 1000 mg L‒1 in 1 M HCl solution.
Microbiotic concentration, mL
Concentration
SIB
110.0
0.0
IB
110.0
0.0
TGB
110.0
70.0
–
0.20 g L‒1
0.02 g L‒1
0.0
1.3
110.0
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STRUCTURE, ANTICORROSION AND ANTIBACTERIAL EVALUATION
757
11. Soltani, N., Behpour, M., Ghoreishi, S.M., and Naeim, H.,
Besides, it displays potent activity against the oilfield
water-borne bacteria, especially for SRB and IB.
Corrosion Science, 2010, vol. 52, p. 1351.
12. Quartertone, G., Bellomi, T., and Zingales, A., Corrosion
Science, 2003, vol, 45, p. 715.
ACKNOWLEDGMENTS
13. Issaadi, S., Douadi,T., Zouaoui,A., Chafa, S., Khan, M.A.,
This work was financially supported by the grants from
National Science Foundation of China (no. 51504193)
and Scientific Research Program Funded by Shaanxi
Provincial Education Department (no. 16JS094).
and Bouet, G., Corrosion Science, 2011, vol. 53, p. 1484.
14. Fang, J. and Li, J., J. Molecular Structure: Theochem.,
2002, vol. 593, p. 179.
15. Behpour, M., Ghoreishi, S.M., Soltani, N., Salavati-
Niasari, M., Corrosion Science, 2009, vol. 51, p. 1073.
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