Synthesis and structure of tetraphenylantimony 1-adamantanecarboxylate and triphenylantimony bis(1-adamantanecarboxylate)

Article abstract of DOI:10.1134/S1070363209100107

Reaction of pentaphenylantimony with triphenylantimony bis(1- adamantylcarboxylate) yielded the solvate of tetraphenylantimony 1-adamantylcarboxylate with benzene. Triphenylantimony bis(1- adamantylcarboxylate) was prepared from triphenylantimony and 1-ad

Full text of DOI:10.1134/S1070363209100107

ISSN 1070-3632, Russian Journal of General Chemistry, 2009, Vol. 79, No. 10, pp. 2131–2136. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © V.V. Sharutin, V.S. Senchurin, O.K. Sharutina, A.P. Pakusina, S.A. Smirnova, 2009, published in Zhurnal Obshchei Khimii, 2009,
Vol. 79, No. 10, pp. 1636–1641.
Synthesis and Structure
of Tetraphenylantimony 1-Adamantanecarboxylate
and Triphenylantimony bis(1-adamantanecarboxylate)
V. V. Sharutin, V. S. Senchurin, O. K. Sharutina, A. P. Pakusina, and S. A. Smirnova
Blagoveshchensk State Pedagogical University,
ul. Lenina 104, Blagoveshchensk, 675000 Russia
e-mail: vvsharutin@rambler.ru
Received April 28, 2008
Abstract―Reaction of pentaphenylantimony with triphenylantimony bis(1-adamantylcarboxylate) yielded the
solvate of tetraphenylantimony 1-adamantylcarboxylate with benzene. Triphenylantimony bis(1-ada-
mantylcarboxylate) was prepared from triphenylantimony and 1-adamantylcarboxylic acid in the presence of
hydrogen peroxide in ether. X-ray studies showed that in the first and in the second product antimony atom has
the distorted trigonal bipyramide coordination (OSbO and CSbO trans-angles are 179.42° and 174.58°,
respectively). Sb–O interatomic distances are 2.154 and 2.202 Å, respectively. The carbonyl group oxygen
atom is coordinated with the central atom, Sb···O interatomic distances are 2.570 and 3.396 Å, respectively.
DOI: 10.1134/S1070363209100107
As known, an effective procedure for preparing the
antimony derivatives of the general formula R4SbOC
(O)R is based on the reaction of penta-
organylantimony with triorganylantimony dicarbo-
xylates [1–3]. The latter compounds are prepared
conveniently by means of oxidative method from
triorganylantimony and carboxylic acid in presence of
peroxide [3–6]. Both these reactions were studied on
the sufficient number of examples, but it was noted
that the increase in size of the organic radical in
carboxylic acid often decreases their efficiency.
Large colorless crystals of compound I well soluble
in the organic solvents were isolated from the reaction
mixture. Yield of the target product reached 92%.
Compounds I, II studied by XRD analysis.
Parameters of the experiment are presented in Table 1,
atomic coordinates and their isotropic equivalent
temperature parameters, in Table 2, and bond angles,
in Table 3. General view of structures of compounds I,
II are presented in Figs. 1, 2.
According to X-ray studies antimony atom in the
molecules of compound I has the distorted trigonal
bipyramide coordination with the oxygen atoms of
carboxylate ligands in the axial positions. OSbO axial
angle (179.42°) has practically the ideal value. Angles
between the axial and equatorial bonds deflect from
their theoretical values on ≈1°. SbC3 group of atoms
has the flat structure (sum of angles in the equatorial
plane is 360°). Deviation from the trigonal bipyramide
coordination is revealed most of all in the values of
CSbC equatorial angles which strongly differ from one
another: 161.48°, 99.26°, and 99.28°. Sb–C inter-
atomic distances are 2.123, 2.127, and 2.127 Å, Their
average value is close to the upper limit of the range of
variation of the mean values of equatorial bonds in the
structurally characterized trialkylantimony dicarbo-
In this study syntheses of triphenylantimony bis(1-
adamantylcarboxylate) I and tetraphenylantimony 1-
adamantylcarboxylate II were carried out, and the
crystalline and molecular structures of these substances
were established.
Reaction of oxidative addition with the par-
ticipation of triphenylantimony, hydrogen peroxide,
and 1-adamantylcarboxylic acid (1:1:2 molar ratio)
proceeds in ether at room temperature to form the
compound I.
Ph3Sb + 2HOC(O)C10H15 + H2O2
Et2O
Ph3Sb[OC(O)C10H15]2 + 2HO2.
I
2131

2132
SHARUTIN et al.
Table 1. Crystallographic data, parameters of the experiment and refining of structures of complexes I and II
Value
Parameter
I
II
М
711.51
687.49
Т, K
90
100
Crystal system
Monoclinic
C2/c
Triclinic
Space group
P–1
a, Å
19.8775(6)
13.0253(4)
12.7896(3)
10.1644(2)
11.4880(2)
14.6546(3)
93.2200(10)
98.2280(10)
107.5380(10)
1605.90(5)
2
b, Å
c, Å
α, deg
β, deg
98.8460(10)
γ, deg
V, Å3
3271.97(16)
Z
4
1.444
ρ(calc), g cm–3
1.422
μ, mm–1
0.885
0.894
F(000)
1472
708
Form of the crystal (size, mm)
Range of data collection by θ, deg
Intervals of reflection indexes
Plate (0.02×0.11×0.18)
1.88–32.47
Plate (0.045×0.145×0.158)
1.87–31.39
–26 ≤ h ≤ 27, –18 ≤ k ≤ 18, –18 ≤ l ≤ 12 –10 ≤ h ≤ 14, –15 ≤ k ≤ 16, –19 ≤ l ≤ 18
Reflections measured
Independent reflections
Refining parameters
GOOF
18474
20128
4763
8648
205
0.999
397
1.078
R factors by F2 > 2σ(F2)
R1 0.0251, wR2 0.0520
R1 0.0394, wR2 0.0658
R factors by all reflections
R1 0.0359, wR2 0.0558
R1 0.0472, wR2 0.0684
Residual electronic density (min/max), e Å–3
–0.375/0.546
–1.291/0.525
xylates (2.100–2.125 Å). Sb–O distances in com-
pound I are equal to one another (2.154 Å). Note that
the largest Sb–O distances were found in triphenyl-
antimony dicynnamate (2.156 Å) [7].
equal to 2.664 Å, and the given ratio is 1.24. Hence, it
may be stated that in the formation of Sb···O=C
intramolecular contacts one of the decisiue factors is
the n-donating ability of the carbonyl oxygen. In the
molecule of compound I the increase in the donating
properties of the carbonyl oxygen atoms is caused by
the positive inductive effect of the hydrocarbon
adamantyl substituents.
In compound I carboxylate ligands are prone to
behave as bidental. Nonvalent interaction of the central
atom with the oxygen atoms of carbonyl groups results
in the significant decrease in Sb···O=C distances which
are equal to 2.570 Å (sum of van der Waals radii of the
antimony and oxygen atoms is 3.70 Å [8]). Symmetry
of coordination of carboxylate ligands on the antimony
atom in product I is the highest in the series of
triorganylantimony dicarboxylates. Hence, the ratio of
the Sb···O=C distance to the length of Sb–O bond
accepted as a measure of dissymmetry of bidentate
ligand for triorganylantimony dicarboxylates as a rule
is 1.31–1.52 while for compound I it is 1.19. In
triphenylantimony dicynnamate Sb···O=C distances are
Sufficiently strong Sb···O=C interactions lead to the
insignificant redistribution of electron density in the
carboxy groups. C–O bond length (1.300 Å) belongs to
the interval of variation of these characteristics in the
carboxylic acids. (1.293–1.308 Å) while the C=O
bonds (1240 Å) are insignificantly larger than the
reported data (1.214–1.229 Å [9]). But the existence of
the Sb···O=C contact causes the distortion of
Sb1O1C1angles (101.56°) as compared to the
theoretical value 120°.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

SYNTHESIS AND STRUCTURE OF TETRAPHENYLANTIMONY
2133
Table 2. Atomic coordinates (×104) and their isotropic equivalent temperature parameters (×103) in the structures I, II
Atom
x
y
z
Ueq, Å2
Atom
x
y
z
Ueq, Å2
II
I
Sb1
O1
O2
C1
0
2124.27(12) 2500
7.54(4)
11.7(2)
13.1(2)
11.0(3)
9.7(3)
C116
2284(2)
3128(2)
3574(3)
2901(3)
1771(3)
1345(3)
2497(2)
1530(2)
946(3)
1154.0(18) 15.7(5)
3916.0(16) 11.8(5)
4637.2(19) 25.0(6)
5401.0(19) 29.2(7)
5439.0(18) 20.4(6)
4733.8(18) 22.6(6)
–1080.7(6)
–764.1(6)
–1227.8(8)
–1971.4(8)
0
2132.6(9)
1957.5(9)
2241.9(9)
1998.8(12)
1748.3(12)
2500
C121
C122
C123
C124
C125
C126
C131
C132
C133
C134
C135
C136
C141
C142
C143
C144
C145
C146
C151
C152
C153
C154
C155
C156
C157
C158
C159
524.6(9)
1157.5(12)
856.2(12)
783(3)
C2
1204(2)
1815(3)
C111
C112
C113
C114
C121
C122
C123
C124
C125
C126
C131
C132
C133
C134
C135
C136
C137
C138
C139
3754.2(17)
4294.6(13)
5363.9(13)
5895.3(18)
1861.5(12)
1290.6(13)
1201.9(13)
1682.9(13)
2262.4(13)
2360.3(13)
1289.1(14)
1319.3(15)
–312.5(13)
1011.6(14)
–155.3(14)
–589.2(13)
10.5(4)
12.1(3)
13.9(3)
14.1(5)
10.8(3)
14.7(3)
17.4(4)
16.1(3)
16.4(3)
13.7(3)
15.7(3)
18.8(4)
15.1(3)
18.1(4)
17.7(4)
17.0(4)
21.7(4)
22.0(4)
23.1(4)
–199.4(8)
–196.0(9)
0
1559.8(13)
1562.3(14)
2500
2022(2)
1985(2) 3968.2(18)
1157(2) 2669.6(16)
2059(2) 3025.5(17)
1824(2) 2995.4(18)
700(2) 2603.2(17)
–192(2) 2241.7(17)
25(2) 2274.6(16)
18.8(5)
11.9(5)
15.0(5)
16.7(5)
15.8(5)
14.6(5)
13.2(5)
11.8(5)
14.3(5)
17.8(5)
18.1(5)
15.6(5)
13.1(5)
14.3(5)
15.3(5)
13.4(5)
16.6(5)
20.8(6)
19.3(5)
19.9(5)
15.0(5)
16.3(5)
5880(2)
7147(2)
8399(2)
8412(2)
7157(2)
5893(2)
4999(2)
5255(2)
6009(2)
6517(2)
6293(2)
5542(2)
192(2)
198.9(8)
–217.3(9)
–54.3(10)
519.1(9)
930.1(9)
769.8(9)
–2276.3(9)
–2356.3(9)
–2055.6(9)
–3034.3(9)
–3112.1(9)
–2812.8(9)
935.1(13)
175.6(13)
–839.1(14)
–1099.4(13)
–347.1(14)
669.1(13)
658.0(13)
2595.2(14)
1731.9(14)
407.4(14)
402.0(14)
1481.8(14)
2325.9(15)
2340.2(15)
1255.8(17)
3567(2) 2821.0(17)
4287(2) 3662.4(17)
5528(2) 3751.6(18)
6064(2) 3001.2(19)
5358(2) 2156.6(18)
4121(2) 2066.4(17)
–3217(2) 2422.8(18)
1774(3) –2353(2) 3937.6(17)
–3191.9(10) –134.9(16)
2767(2)
–32(2)
–2882(2) 2566.6(17)
–4523(2) 2701.3(18)
–4491(2) 3758.3(19)
–3665(2) 4218.7(18)
–4160(2) 3892.2(18)
–4190(2) 2838.0(18)
–5018(2) 2377.2(18)
–3115.5(9)
–3410.2(9)
1032.6(16)
1471.7(15)
II
98(3)
1551(3)
2665(3)
2544(2)
1086(2)
Sb1
O1
O2
3989.24(16) 1594.13(14)
2680.16(11)
2620.2(11)
2525.7(12)
8.43(4)
13.0(3)
17.0(4)
3144.5(16)
862.3(17)
–418.1(14)
–634.2(15)
C1
1850(2)
1652(2)
2727(2)
–1048(2)
–2367(2)
1497(2)
2647.8(16)
2877.5(16)
1383.6(16)
11.2(5)
10.8(5)
11.2(5)
C3
C4
C5
6561(3)
5443(3)
5565(3)
4131(2) –292.0(19)
3057(3) –457.1(18)
23.8(6)
23.1(6)
20.3(6)
C2
C111
2007(2)
–89.2(18)
C112
C113
C114
C115
2391(2)
1650(2)
1219(2)
1518(3)
476(2)
470(2)
1465(2)
2466(2)
736.2(17)
–137.4(17)
–368.4(18)
285.7(19)
13.9(5)
17.1(5)
19.8(5)
21.0(6)
C6
C7
C8
6804(3)
7932(3)
7809(3)
2021(2)
3090(2)
4143(2)
448.5(18)
611.8(19)
238.9(19)
20.4(6)
22.3(6)
24.5(6)
Carboxylate ligands have a cis-orientation were
respect to the SbC3 ligand (dihedral angle between the
planes of carboxy groups is 15.25°) what causes a
significant increase in one of the equatorial angles
C121Sb1C121a to 161.48°.
As four oxygen atoms and C111 carbon atom of one
of the phenyl rings are located approximately in the
same plane as the antimony atom, it may be considered
as the equatorial plane of pentagonal bipyramid whose
axial positions are occupied by C121 and C121a atoms of
two phenyl groups.
Molecule of compound I has its own non-
crystallographic C2v symmetry. The second order axis
passes through the C114 and C111 atoms of the phenyl
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2134
SHARUTIN et al.
Table 3. Interatomic distances and bond angles in the structures I, II
Bond d, Å
Bond angle ω, deg
Bond d, Å
Bond angle ω, deg
C111Sb1O1
I
II
Sb1–O1
Sb1–C111
Sb1–C121
Sb1–O2
O1–C1
2.1536(11)
2.123(2)
2.127(2)
2.570(1)
1.306(2)
1.240(2)
1.515(2)
1.539(2)
1.542(2)
1.531(2)
1.397(2)
O1#1Sb1O1 a
179.43(6)
89.71(3)
Sb1–O1
Sb1–C111
Sb1–C121
Sb1–C131
Sb1–C141
Sb1–O2
O1–C1
2.202(2)
2.112(2)
2.117(2)
2.129(2)
2.172(2)
3.396(2)
1.305(3)
1.229(3)
1.530(3)
1.540(3)
1.540(3)
1.538(3)
1.390(3)
1.396(3)
88.68(8)
120.50(9)
117.03(9)
96.15(9)
82.84(7)
119.39(9)
96.77(9)
80.95(7)
94.60(8)
174.57(7)
125.93(14)
113.98(19)
124.3(2)
121.7(2)
C111Sb1O1
C111Sb1C121
C121Sb1O1#1
C121Sb1O1
C121Sb1C121#1
C1O1Sb1
C111Sb1C121
C111Sb1C131
C111Sb1C141
C121Sb1O1
C121Sb1C131
C121Sb1C141
C131Sb1O1
C131Sb1C141
C141Sb1O1
C1O1Sb1
99.26(4)
89.05(5)
91.04(5)
O2–C1
161.47(8)
101.56(10)
117.41(14)
119.62(15)
122.96(14)
120.25(11)
C1–C2
C2–C131
C2–C132
C2–C133
O1C1C2
O2–C1
C1–C2
O2C1O1
O2C1C2
C2–C151
C2–C152
C2–C153
C111–C112
C111–C116
C111–C112#1
C112C111Sb1
O1C1C2
O2C1O1
O2C1C2
a Symmetric transformations: #1 –x, y, –z + 1/2
ligand, through the Sb1–C111 bond and divides in half
the bond angle between two equivalent carboxylate
substituents. Adamantyl groups of carboxylate ligands
have the eclipsed conformation.
Ph5Sb + Ph3Sb[OC(O)C10H15]2
PhH
2Ph4SbOC(O)C10H15⋅PhH.
II
Reaction was carried out in the aromatic hydro-
carbon solution at room temperature, but the short time
heating of reaction mixture on a boiling water bath is
needed for its completion.
It is established that pentaphenylantimony reacts
with triphenylantimony bis(1-adamantylcarboxylate)
to form the solvate of tetraphenylantimony 1-ada-
mantylcarboxylate with benzene in 88% yield.
C124a
C123a
C125a
C126a
C122a
C113a
C121a
O2
C132
C138
C137
C139
C1
O1
C2
C136
C133
Sb1
C121
C113
C122
C135
C131
C134
C126
C125
C123
C124
Fig. 1. Spatial arrangement of compound I.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

SYNTHESIS AND STRUCTURE OF TETRAPHENYLANTIMONY
2135
According to X-ray data antinomy atom in
compound II has the distorted trigonal bipyramid
coordination which is revealed in the deviation of all
bond angles of the antimony atom from the theoretical
values. Hence, axial CSbO angle is 174.58°, CSbC
angles in the equatorial plane are 117.03, 119.39, and
120.50° (total 356.9°). The angles between the axially
located oxygen atom and the equatorial carbon atoms
OSbCeq are smaller than 90° (80.94°, 82.85°, 88.68°),
while the values of CaxSbCeq angles are larger (96.15°,
96.77°, 94.60°). All the presented data agree with the
values observed usually for tetraarylantimony car-
boxylates [10].
Interatomic distances (C=O and C–O) in compound
II (1.229 and 1.304 Å) coincide with the data for
carboxylic acids. SbO1C1 angle is equal to 125.93°.
Hence, it was established that the reaction of
oxidative addition and redistribution of ligands leads to
the synthesis of triphenylantimony bis(1-adamantyl-
carboxylate) I and tetraphenylantimony 1-adaman-
tylcarboxylate II respectively in high yields. The trend
to show bidentate properties by adamantly-carboxylate
ligands depends on the type of compound.
EXPERIMENTAL
X-ray study of crystals of compounds I and II was
carried out on an automatic four-circle Bruker-Nonius
X8Apex diffractometer (two-coordinate CCD detector)
using the MoKα radiation, λ = 0.71073 Å and graphite
monocromator. Reflection intensities were measured
by means of φ-scanning of the narrow (0.5°) frames up
to 2θ 50°. The extination was accounted for
empirically (SADABS) [11]. Structure was solved by
the direct method and refined by means of the full-
matrix root-mean-square method in the anisotropic
approximation for the nonhydrogen atoms (SHELX-
97) [12].
Sb–Ceq Distances (2.112, 2.117, 2.127 Å) are
shorter than the axial Sb–C bond (2.172 Å). In tetra-
arylantimony carboxylates the interval of variation of
the mean values of equatorial bonds is 2.079–2.127 Å
while for the axial ones it is 2.117–2.180 Å [10]. Sb–O
bond (2.202 Å) is abnormally short, while Sb···O=C
intramolecular distance (3.396 Å) is the longest in the
series of tetraarylantimony carboxylates (2.223–
2.530 Å and 3.112–3.509 Å respectively). The coordina-
tion dissymmetry of carboxylate ligand in the product
II is evaluated at 1.54. Hence, the higher is the
strength of the covalent Sb–O bond the weaker is the
donor-acceptor interaction with the participation of d-
orbitals of the metal atom and the unshared electron
pair of oxygen.
Main crystallographic data and the results of
refining of structures are listed in Table 1, the
coordinates and temperature factors of atoms in Table 2,
C124
C125
C126
C143
C123
C142
C144
C122
C121
Sb1
C141
C116
C145
C152
O2
C156
C146
C115
C1
C155
C151
C154
C111
C157
C2
O1
C114
C7
C8
C4
C153
C3
C112
C158
C113
C159
C6
C5
Fig. 2. Spatial arrangement of compound II.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2136
SHARUTIN et al.
soedinenii (Synthesis and Some Reactions of the
Organoantimony Compounds), Blagoveshchensk, Izd.
Dal’GAU, 2005.
and the main interatomic distances and bond angles, in
Table 3.
IR spectra were recorded on the IR Fourier
spectrometer from KBr pellets.
2. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P., and
Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9,
p. 1538.
Triphenylantimony bis(1-adamantylcarboxylate)
(I). A mixture of 0.50 g of triphenylantimony, 0.51 g
of 1-adamantylcarboxylic acid, and 20 ml of diethyl
ether was treated with 0.16 ml of 30% hydrogen
peroxide and kept for 18 h at 20oC. Crystals of the
compound I were formed, yield 0.92 g (92%), mp 228°C.
IR spectrum, ν, cm–1: 3048, 2930, 2849, 1597, 1571,
1495. 1452, 1429, 1284, 1251, 1186, 1103, 1084,
1063, 1019, 997, 913, 810, 732, 695, 529, 460. Found,
%: C 67.32, H 6.30. C40H45O4Sb. Calculated, %: C
67.51, H 6.33.
3. Sharutin, V.V., Senchurin, V.S., Sharutina, O.K.,
Pakusina, A.P., and Panova, L.P., Zh. Obshch. Khim.,
1996, vol. 66, no. 10, p. 1755.
4. Sharutin,, V.V., Sharutina,, O.K., Bondar’, E.V., Paku-
sina, A.P., Adonin, N.Yu., and Starichenko, V.F., Zh.
Obshch. Khim., 2002, vol. 72, no. 3, p. 419.
5. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A.,
Pakusina, A.P., Gatilov, Yu.V., and Adonin, N.Yu.,
Koord. Khim., 2002, vol. 28, no. 5, p. 356.
6. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P.,
Platonova, T.P., Zhidkov, V.V., Pushilin, M.A., and
Gerasimenko, A.V., Koord. Khim., 2003, vol. 29, no. 10,
p. 750.
Tetraphenylantimony 1-adamantylcarboxylate
(II). A mixture of 0.51 g of pentaphenylantimony,
0.71 g of triphenylantimony bis(1-adamantylcarboxylate)
and 10 ml of benzene was heated for 15 min on a
boiling water bath and concentrated to ~2 ml. The
crystals formed were filtered off and dried to give 1.22 g
(88%) of compound II, mp 165oC. IR spectrum, ν, cm–1:
3048, 2913, 1634, 1575, 1479, 1433, 1317, 1188,
1065, 1000, 910, 813, 736, 690, 464. Found, %: C
70.71, H 6.09. C41H41O2Sb. Calculated, %: C 71.62, H
5.97.
7. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P.,
Platonova, T.P., Smirnova, S.A., Pushilin, M.A., and
Gerasimenko, A.V., Khimiya i khimocheskoe mode-
lirovanie. Butlerovskie soobshcheniya (Chemistry and
Chemical Modeling. Butlerov Reports), 2003, no. 1, p. 26.
8. Batsanov, S.S., Zh. Neorg. Khim., 1991, vol. 36, no. 11,
p. 3015.
9. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L.,
Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin
Trans 2, 1987, no. 12, part 2, p. 1.
ACKNOWLEDGMENTS
Authors express their gratitude to E.V. Peresypkin
research of Institute of Inorganic Chemistry of the
Sibirian Branch of Russian Academy of Sciences
(Novosibirsk) for the X-ray studies of compounds I
and II.
10. Sharutin, V.V., Pakusina, A.P., Sharutina, O.K.,
Platonova, T.P., Smirnov S.A., Gerasimenko, A.V., and
Pushilin, M.A., Khimiya i khimicheskoe modelirovanie
(Chemistry and Chemical Modeling. Butlerov Reports),
2003, no. 1, p. 22.
11. Sheldrick, G.M., SADABS, Program for Empirical X-
ray Absorption Vorrection, Bruker-Nonius, 1990–2004.
REFERENCES
12. Sheldrick, G.M., SHELX-97 Release 97-2, University of
1. Pakusina, A.P., Sharutin, V.V., and Sharutina, O.K.,
Göttingen, Germany, 1998.
Sintez
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