β,β-Dinitrostyrenes: Specificity of synthesis and structure

Article abstract of DOI:10.1134/S1070363207110114

An improved procedure was developed for the synthesis of β,β-dinitrostyrenes, which increased the yield and reproducibility and made the products more accessible from the preparative viewpoint. Complex analysis of the spectral data (IR, UV, ¹H

Full text of DOI:10.1134/S1070363207110114

ISSN 1070-3632, Russian Journal of General Chemistry, 2007, Vol. 77, No. 11, pp. 1912 1918.
Pleiades Publishing, Ltd., 2007.
Original Russian Text V.M. Berestovitskaya, E.A. Pabolkova, A.V. Belyakov, E.V. Trukhin, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77,
No. 11, pp. 1859 1865.
, -Dinitrostyrenes: Specificity of Synthesis and Structure
V. M. Berestovitskayaa, E. A. Pabolkovaa, A. V. Belyakovb, and E. V. Trukhina
a Hertzen Russian State Pedagogical University,
nab. r. Moiki 48, St. Petersburg, 191186 Russia
e-mail: kohrgpu@yandex.ru
b St. Petersburg State Institute of Technology,
Moskovskii pr. 26, St. Petersburg, 190013 Russia
Received March 28, 2007
Abstract An improved procedure was developed for the synthesis of , -dinitrostyrenes, which increased
the yield and reproducibility and made the products more accessible from the preparative viewpoint. Complex
1
analysis of the spectral data (IR, UV, H and 13C NMR) and results of quantum-chemical calculations showed
that 2-aryl-1,1-dinitroethene molecules have a structure in which one nitro group resides in the C=C bond
plane while the other deviates from this plane. The C=C bond in 2-aryl-1,1-dinitroethene molecules was found
to possess enhanced polarization and electrophilicity as compared to the corresponding bond in model mono-
nitrostyrenes.
DOI: 10.1134/S1070363207110114
Conjugated nitro alkenes attract increased interest
as convenient models for studying general theoretical
problems of organic chemistry, as well as starting
compounds for the synthesis of practically important
substances (drugs, pesticides, analogs of naturally
occurring compounds, energetic materials, etc.) [1 3].
In particular, just -nitrostyrene was the key com-
pound in the first synthesis of Fenibut, a novel non-
toxic nootropic agent used in medical practice [4, 5].
convenient models for studying specificity of the
effect of two nitro groups on the reactivity of the
double bond in comparison with mononitrostyrenes
and their derivatives containing a different substituent
(halogen atom, acetyl group, etc.) at the same carbon
atom. In this connection, we thought it to be expe-
dient to examine in detail the structure of , -dinitro-
styrenes with a view to elucidate their synthetic
potential as starting materials for purposeful prepara-
tion of functionally substituted structures.
Introduction of the second nitro group into mono-
nitroethene molecules enhances electrophilicity of the
double C=C bond thus giving rise to qualitatively new
highly reactive compounds [6 8]. Typical representa-
tives of this series are geminal dinitrostyrenes that are
Geminal dinitrostyrenes IV VI were prepared ac-
cording to improved procedures [6, 7] by nitration of
the corresponding mononitrostyrenes I III with
almost tenfold excess of dinitrogen tetraoxide in
carbon tetrachloride at 16 18 C.
5
4
NO2
NO2
1
2
1
2
R6
N2O4
3
CHA=C
CHA=CHB NO2
R
7
8
I III
IV VI
I, IV, R = H; II, V, R = Cl; III, VI, R = CH3.
After removal of the solvent and excess nitrating
agent, the mixture was treated with propan-2-ol at
16 18 C instead of ethanol at 5 C as recommended
in [7]. It is known that ethanol adds to , -dinitro-
styrenes at room temperature almost instantaneously
[8], while low-temperature treatment complicates the
experimental procedure. The use of propan-2-ol at
room temperature allowed us to simplify isolation of
the resulting dinitrostyrenes, improve their yield (from
42.5 to 79% for compound IV and from 39.5 to 49%
for V), and made the procedure readily reproducible
and preparatively accessible (Table 1).
1912

, -DINITROSTYRENES: SPECIFICITY OF SYNTHESIS AND STRUCTURE
1913
1
Table 1. Yields and IR, UV, and H and 13C NMR spectra of , -dinitrostyrenes IV VI and -nitrostyrenes I III
IR spectrum, (CHCl3),
UV spectrum
(CHCl3)
NMR spectra (CDCl3), , ppm
1H 13C
1
, cm
Yield
(published
data), %
Comp.
no.
a
NO2
(
)
C=C, Ar
1645
max, nm
HA (HB)
Ar
C1
C2
I
1530, 1345
(185)
243
313
244
324
242
328
245
342
244
328
242
341
5400
17900
8600
17200
11800
31600
20100
40000
8300
7.87
(7.60)
8.03
7.38
137.1
149.0
137.5
149.2
136.3
148.9
138.9
127.2
137.7
126.2
139.1
127.5
IV
II
79
(42.5)
1550, 1320
(230)
1525, 1340
(185)
1610
1650
1630
7.47 7.68
7.37
7.75
(7.47)
7.98
V
49
(39.5)
1550, 1320
(230)
1520, 1340
(180)
1600
1645
1630
7.39 7.55
7.33
III
VIb
7.95
(7.54)
7.96
21000
10800
23400
65
1550, 1320
(230)
1610
1640
7.27 7.45
(65)
a
b
Broadened bands.
Chemical shifts of the CH group:
2.46 ppm,
21.6 ppm.
C
3
We thus obtained a series of , -dinitrostyrenes,
including those having electron-withdrawing (Cl) and
electron-donor substituents (CH3) in the para position
of the benzene ring and no substituent therein. It
should be noted that the melting point of a sample of
VI isolated by us (70 71 C) considerably differed
from the melting point given in [7] (52 54 C); pre-
sumably, the latter is invalid, for the structure of our
sample was reliably confirmed by independent
methods (IR, UV, and 1H and 13C NMR spectra).
C=C bond and aromatic ring (1600 1610, 1640
1650 cm ; Table 1). The difference between the fre-
quencies of antisymmetric and symmetric vibrations
1
of the nitro groups in compounds IV VI is
=
as
s
1
230 cm , which is typical of geminal dinitro-
styrenes [12]; the corresponding difference for mono-
1
nitrostyrenes is 180 185 cm .
The electronic absorption spectrum of the simplest
, -dinitrostyrene (IV) in cyclohexane was reported
in [13]:
224 nm ( = 8415),
313 nm ( =
max1
max2
15850) [13]; only the positions of long-wave absorp-
tion maxima in the spectra of V and VI in dioxane
Aryldinitroethenes IV VI are light yellow crystal-
line substances that are fairly stable. They can be
stored for 1 1.5 month at room temperature, and then
slow decomposition begins. To prolong their lifetime,
compounds IV VI should be stored at reduced
temperature. It should be noted that the simplest
representative of this series, 1,1-dinitroethene, was
not isolated individual; it is generated in situ from
appropriate functionally substituted precursors [9 11].
were given in [7]:
329 and 334 nm, respectively.
Comparison of the mealxectronic absorption spectra of
dinitrostyrenes IV VI in chloroform ( 242
245 nm,
324 342 nm) with those omfax1 -nitro-
styrenes ( max2 242 244 nm,
313 328 nm) [13]
shows thatmaixn1troduction of the second nitro group
induces a small red shift ( 13 nm) of the long-
wave absorption band (Table 1). A red shift of the
long-wave absorption maximum ( 17 nm) is also
max2
max2
The structure of geminal dinitrostyrenes IV VI
was studied by spectral methods (1H and 13C NMR,
IR, UV) and quantum-chemical calculations (B3LYP/
6-31+G*) with a view to analyze specificity of their
structure as compared to mononitrostyrene.
observed in going from compound IV to V and VI
where the substituent exerts mesomeric of hypercon-
jugation effect.
The 1H NMR parameters of , -dinitrostyrenes
IV VI [ 7.96 8.03 (CHA), 7.27 7.68 ppm (Harom)]
almost coincide with those reported for 1,1-dinitro-2-
phenylethene [CDCl3: 8.00 (CHA), 7.49 ppm (Harom)]
[14] and are close to the corresponding parameters of
2-nitro-3-phenylacrylonitrile [ 7.83 (CHA), 6.65
The IR spectra of , -dinitrostyrenes IV VI
contain strong broadened absorption bands typical of
1
conjugated nitro group (1550 and 1320 cm ) and
bands belonging to stretching vibrations of the
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 11 2007

1914
BERESTOVITSKAYA et al.
Table 2. Bond angles (deg) in molecules I and IV VI
software package [19] in terms of the density func-
tional theory [20] (B3LYP/6-31+G*) with account
taken of diffuse and polarization functions. Analogous
calculations were also performed for 1-nitro-2-phenyl-
ethene (I) as model structure, The principal geometric
parameters of molecules I and IV VI are given in
Tables 2 4, and the molecular models are shown in
figure.
Comp.
no.
C3C2C1
C2C1N9 C2C1N12 N9C1N12
IV
V
VI
I
131.9
131.6
131.9
126.9
121.9
121.9
122.0
120.6
125.9
125.8
125.8
112.2
112.2
112.2
It is seen that the plane of one of the nitro groups
considerably declines from the plane of the arylnitro-
ethene fragment. The torsion angles C3C2C1N9,
C2C1N9O10, and C2C1N9O11 in molecules I (180.0,
180.0, and 0.0 , respectively) and IV VI (179.7
180.0, 178.2 178.7, and 1.1 1.5 , respectively; Tables
2, 3) indicate planar structure of the arylnitroethene
fragment. On the other hand, the torsion angles
C3C2C1N12 ( 0.5 to 0.9 ), C2C1N12O13 (85.0 to
86.3 ), C2C1N12O14 ( 92.0 to 93.3 ), N9C1N12O13
( 94.8 to 95.7 ) and N9C1N12O14 (85.9 to 86.9 ) in
, -dinitrostyrene molecules correspond to almost
orthogonal orientation of the second nitro group with
respect to the arylnitroethene fragment. Therefore,
interaction of between the second nitro group and the
C=C bond is weakened.
According to the calculations, the C1=C2 bond
length (Table 4) almost does not change in going from
mononitrostyrene to geminal dinitrostyrene, and it
remains similar to the C=C bond length in nitroethene
and its monosubstituted analogs (1.34 1.32 ) [21
29]. The C1 N9 bond length in , -dinitrostyrenes
IV VI (1.455 1.458 ) is close to that in -nitro-
styrene. However, this bond in molecules I and IV
VI is shorter than in nitroethene (1.451 for I against
1.470 in nitroethene [21]); undoubtedly, the reason
is extension of the conjugation system due to the
presence of phenyl substituent.
7.45 ppm (Harom)] [14]. It is important that the ole-
finic protons in IV VI resonate in a weaker field (
7.83 8.03 ppm) than the aromatic protons ( 6.65
7.68 ppm). Undoubtedly, joint deshielding effect of
two nitro groups is responsible for the more downfield
position of the olefinic proton signals of , -dinitro-
styrenes relative to the corresponding signals of
mononitrostyrenes ( 7.47 7.60 ppm) (Table 1).
The 13C NMR spectra of IV VI, recorded without
decoupling from protons, contain a strong doublet
signal from C2 at
126.2 127.5 ppm (JCH =
C
162.8 Hz) and a downfield singlet at
148.9
C
149.2 ppm due to resonance of the C1 nuclei; signals
from aromatic carbon nuclei appear in the region
C
122.5 145.8 ppm (Table 1). It is seen that , -dinitro-
styrenes are characterized by more downfield position
of the C1 signal ( 148.9 149.2 ppm) as compared
C
to mononitrostyrenes (Table 1), which results from
deshielding effect produced by two nitro groups. It
should be noted that the resonance signals of C1 are
broadened due to coupling with quadrupolar 14N
nuclei [15 18].
To estimate the degree of polarization and elucidate
electronic and steric structure of compounds IV VI
we performed quantum-chemical calculations of
geometric parameters of their molecules, dipole mo-
ments, and charges on atoms using Gaussian 03w
The difference between the lengths of the C1 N9
Table 3. Torsion angles
(deg) in molecules I and IV VI
Comp. no.
C3C2C1N9
C3C2C1N12
C2C1N9O10
C2C1N9O11
IV
V
VI
I
179.8
179.7
180.0
180.0
0.7
0.9
0.5
178.2
178.7
178.2
180.0
1.5
1.1
1.5
0.008
Comp.
C2C1N12O13
C2C1N12O14
N9C1N12O13
N9C1N12O14
IV
V
VI
85.1
86.3
85.0
93.2
92.0
93.3
95.7
94.8
95.6
85.9
86.9
86.2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 11 2007

, -DINITROSTYRENES: SPECIFICITY OF SYNTHESIS AND STRUCTURE
1915
(a)
H12
C4
H13
H18
C2
O10
C1
C5
N9
C3
C8
H14
O11
C6
H17
C7
H15
H16
C6
O14
N12
O13
(b)
H15
C4
C5
H17
C1
O18
C3
C2
C7
N9
C8
H19
H20
O11
H18
H17
(c)
O14
N12
O13
H16
O10
C4
C3
C5
C1
C2
C15
N9
C6
C8
O11
C7
H20
H18
H17
(d)
O14
N12
H16 O13
H21
C4
H22
C15
H23
O10
N9
C5
C6
C1
C3
C2
C8
C7
O11
H20
H18
H19
Molecular models of (a) 1-nitro-2-phenylethene (I), (b) 1,1-dinitro-2-phenylethene (IV), (c) 2-(p-chlorophenyl)-1,1-dinitro-
ethene (V), and (d), 1,1-dinitro-2-(p-tolyl)ethene (VI), calculated at the B3LYP/6-31+G* level.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 11 2007

1916
BERESTOVITSKAYA et al.
Table 4. Bond lengths d ( ) in molecules I and IV VI
1-ethoxycarbonylethene (1.472 ) [30], where the
nitro group is also forced out of the double bond plane.
Comp. no.
C1=C2
C1 N9
C1 N12
Effective charges on atoms (q) are parameters that
characterize electronic structure of molecules. We
used natural charges. Analysis of the populations
calculated in the B3LYP/6-31+G(d) approximation
was performed in terms of the NBO approach (Natural
bond orbitals, Version 3.1, Gaussian-03w) [31].
Natural charges reproduce electron density distribu-
tion more accurately than total Mulliken charges [32].
The calculations showed that introduction of the
second nitro group reduces the negative charge on C2,
the charge on C1 changes correspondingly (Table 5).
The calculated charges on the double-bonded carbon
atoms correlate with the 13C NMR data [17]. Contrast-
ing charge distribution and strong difference in the
2
IV
V
VI
I
1.343
1.342
1.344
1.343
1.458
1.458
1.455
1.451
1.474
1.474
1.474
Table 5. Calculated charges on the C1 and C2 atoms and
dipole moments of compounds IV VI
Charge (NBO)
, D
Conmo.p.
experimental
C1
C2
calculateda
[13, 33]
5.28
chemical shifts of C1 and C2 (
=
C ) are
C
C1
IV
V
VI
I
0.192
0.194
0.188
0.110
0.150
0.154
0.149
0.160
7.12
5.71
8.04
6.36
responsible for the high dipole moments. Although
the calculated and experimental dipole moments
[13, 33] differ considerably, the character of their
variation in going from mono- to dinitrostyrenes is
the same: the dipole moment increases (Table 5).
4.32
a
B3LYP/6-31+G*.
Our results suggest that the C=C bond in geminal
dinitrostyrenes is strongly electron-deficient and that
the most electron-deficient is the carbon atom bearing
two nitro groups. On the other hand, reactions with
nucleophiles involve the C2 atom, as in -nitrostyrene,
for the corresponding intermediate anion is more
stable than that formed via alternative nucleophilic
attack at C1.
(1.455 1.458 ) and C1 N12 bonds (1.474 ) must
be noted. It seems to be expected taking into account
that the second nitro group (N12) interacts with the
double bond less effectively than does the first nitro
group (N9). The C1 N12 bond length (1.474 ) ap-
proaches those found in 1-acetyl-1-nitro-2-(p-methoxy-
phenyl)ethene (1.476 ) and 1-nitro-2-(p-nitrophenyl)-
O
N
NO2
NO2
NO2
O
NO2
NO2
EtOH
Ar CH CH
Ar CH C
Ar CH C
Ar CH=C
O
NO2
+
+
N
EtOH
EtOH
O
Thus, joint analysis of the spectral data and results
of quantum-chemical calculations allowed us to
characterize molecules of , -dinitrostyrenes IV VI
as structures with nonequivalent nitro groups with
respect to their interaction with the C=C bond; en-
hanced polarization and electrophilicity of the latter
was assessed in comparison with model mononitro-
styrene.
as solvent and hexamethyldisiloxane as reference
(internal or external); the chemical shifts were de-
termined with an accuracy of 0.5 Hz. The IR spectra
were recorded on an InfraLYuM FT-02 spectrometer
1
in chloroform (c = 40 mg ml ). The electronic ab-
sorption spectra were measured from solutions in
chloroform on an SF-2000 spectrophotometer using
quartz cells (cell path length 1 cm).
EXPERIMENTAL
Quantum-chemical calculations of
, -dinitro-
1
The H NMR spectra were measured on a Bruker
styrenes IV VI and model -nitrostyrene (I) were
performed using Gaussian 03w software package [19]
AC-200 spectrometer (200 MHz) using chloroform-d
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 77 No. 11 2007

, -DINITROSTYRENES: SPECIFICITY OF SYNTHESIS AND STRUCTURE
1917
in terms of the density functional theory [20] at the
B3LYP/6-31+G* level of theory with account taken
of diffuse and polarization functions.
5. Berestovitskaya, V.M., Zobacheva, M.M., and Vasil’e-
va, O.S., Izv. Ross. Gos. Ped. Univ. im. A.I. Gertsena
(estestv. toch. nauki), 2002, no. 2 (4), p. 133.
6. Novikov, S.S., Belikov, V.M., Dem’yanenko, V.F.,
and Lapshina, L.V., Izv. Akad. Nauk SSSR, Ser. Khim.,
1960, no. 7, p. 1295.
Initial 1-nitro-2-phenylethene (I), 1-(p-chloro-
phenyl)-2-nitroethene (II), and 1-nitro-2-(p-tolyl)-
ethene (III) were prepared according to the procedures
reported in [34 37]. 1,1-Dinitro-2-arylethenes IV VI
were synthesized by improved procedures [6, 7].
7. Kim, T.R., Lee, Y.H., and Chai, W.S., Igong Nonjip.,
1985, vol. 26, no. 6, p. 195; Chem. Abstr., 1987,
vol. 107, no. 58577n.
1,1-Dinitro-2-phenylethene (IV). A solution of
17 ml of dinitrogen tetraoxide in 14 ml of anhydrous
carbon tetrachloride was added to a suspension of
4.00 g of 1-nitro-2-phenylethene (I) in 26 ml of an-
hydrous carbon tetrachloride, and the mixture was left
to stand for 7 days at 16 18 C. Excess nitrating agent
and the solvent were evaporated in the cold, the oily
residue was treated with propan-2-ol, and the pre-
cipitate was filtered off. Yield 4.16 g (79%), light
yellow crystals, mp 93 94 C (from anhydrous carbon
tetrachloride); published data: mp 94 95 C (from
CCl4), yield 39% [6], 42.5% [7]. Found, %: C 49.60,
49.58; H 3.14, 3.12; N 14.40, 14.42. C8H6N2O4.
Calculated, %: C 49.48; H 3.09; N 14.43.
8. Jamamura, K., Watarai, S., and Kinugasa, T., Bull.
Chem. Soc. Jpn., 1971, vol. 44, no. 9, p. 2440.
9. Bagal, L.I., Tselinskii, I.V., and Shokhor, I.N., Zh.
Org. Khim., 1969, vol. 5, no. 11, p. 2016.
10. Fridman, A.L., Gabitov, F.A., and Surkov, V.D., Zh.
Org. Khim., 1972, vol. 8, no. 12, p. 2457.
11. Baum, K., Bigelov, S.S., and Nguyen, N.V., Tetra-
hedron Lett., 1992, vol. 33, no. 16, p. 2141.
12. Paperno, T.Ya. and Perekalin, V.V., Infrakrasnye
spektry nitro soedinenii (Infrared Spectra of Nitro
Compounds), Leningrad: Leningr. Gos. Ped. Inst.,
1974.
13. Skulski, L. and Plenkiewicz, J., Roszn. Chem., 1963,
2-(p-Chlorophenyl)-1,1-dinitroethene (V) was
synthesized in a similar way from 1-(p-chlorophenyl)-
2-nitroethene (II). Yield 2.24 g (49%), light yellow
crystals, mp 70 71 C (from hexane); published data
[7]: mp 69 70 C (from CCl4), yield 39.5%. Found,
%: C 42.12, 42.10; H 2.24, 2.23; N 12.22, 12.24.
C8H5ClN2O4. Calculated, %: C 42.01; H 2.19;
N 12.25.
vol. 37, no. 1, p. 45.
14. Benhaoua, H., Piet, J.-C., Danion-Bougot, R., Tou-
et, L., and Carrie, R., Bull. Soc. Chim. Fr., 1987,
no. 2, p. 325.
15. Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR
spektroskopiya v organicheskoi khimii (NMR Spec-
troscopy in Organic Chemistry), Leningrad: Khimiya,
1983.
1,1-Dinitro-2-( p-tolyl)ethene (VI) was syn-
thesized in a similar way from 1-nitro-2-(p-tolyl)-
ethene (III). Yield 2.70 g (65%), light yellow crystals,
mp 70 71 C (from hexane); published data [7]: mp
52 54 C (from CCl4), yield 65.0%. Found, %: C
51.71, 51.70; H 4.05, 4.03; N 13.64, 13.67.
C9H8N2O4. Calculated, %: C 51.92; H 3.85; N 13.46.
16. Ershov, B.A., Spektroskopiya YaMR v organicheskoi
khimii (NMR Spectroscopy in Organic Chemistry),
St. Petersburg: S.-Peterb. Gos. Univ., 1995.
17. Levy, G.C. and Nelson, G.L., Carbon-13 Nuclear
Magnetic Resonance for Organic Chemists, New
York: Wiley, 1972.
18. Gan, Z. and Grant, D.M., J. Magn. Reson., 1990,
vol. 90, no. 3, p. 522.
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