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DOI: 10.14529/chem170207
THE OXIDATIVE-ADDITION REACTIONS OF TRI(META-TOLYL) ANTIMONY AND TRI(ORTHO-TOLYL)ANTIMONY WITH 5-NITROFURFURALDOXIME IN THE PRESENCE OF PEROXIDES. THE MOLECULAR STRUCTURES OF M2-OXO-B/S[(5-NITROFURFURALDOXIMATO)TRI(META-TOLYL)ANTIMONY] AND m2-OXO-B/S[(5-NITROFURFURALDOXIMATO)TRI(ORTHO-TOLYL)ANTIMONY]
E.V. Artemeva, [email protected] M.S. Makerova, [email protected] V.V. Sharutin, [email protected] O.K. Sharutina, [email protected]
South Ural State University, Chelyabinsk, Russian Federation
The interaction of tri(meta-tolyl)antimony and tri(ortho-tolyl)antimony with 5-nitro-furfural oxime in the presence of an oxidizing agent (hydrogen peroxide or tert-butyl hydroperoxide) leads to the formation of bis(5-nitrofurfuraldoximato)tri(meta-tolyl)antimony (1), ^2-oxo-bis[(5-mtrofurfuraldoximto)tri(meta-tolyl)antimony] (2), bis(5-nitrofurfuraldoximato) tri(ortho-tolyl)antimony (3) and ^2-oxo-bis[(5-nitrofurfuraldoximato)tri(ortho-tolyl)antimony] (4). The molecular structures of complexes 2 and 4 have been determined by X-ray diffraction analysis.
Keywords: tri(m-tolyl)antimony, tri(o-tolyl)antimony, 5-nitrofurfuraldoxime, tert-butyl hydroperoxide, hydrogen peroxide, oxidation, bis(5-nitrofurfuraldoximato)tri(m-tolyl) antimony, ¡x2-oxo-bis[(5-nitrofurfuraldoximato)tri(m-tolyl)antimony], ¡i2-oxo-bis[(5-nitrofurfur-aldoximato)tri(o-tolyl)antimony], molecular structures, X-ray diffraction analysis.
Introduction
It is known that some pentavalent antimony derivatives are biologically active compounds. For example, triphenyl- and trimethylantimony dioximates and dicarboxylates were observed to have bactericidal and antitumor activity [1-6]. One of the methods allowing such compounds to be synthesized is the oxidative synthesis. It is interesting to note that two types of triarylantimony dioximates (ArsSbX2 or (A^SbX^O (Ar = Ph, p-Tol, o-Tol; X = ONCHR, ONCRR') can be obtained, depending on the oxime nature and the reaction conditions [7-10].
Oximes that contain two donor atoms (O and N) are ampolydentate ligands. However, according to X-ray diffraction data, the ligands of such antimony derivatives as Ar3Sb(ONCRR')2 and (Ar3SbONCRR')2O are usually bound to the antimony atom only via the oxygen atom. In this case, short distances between the antimony atom and the nitrogen atoms of iminoxy-groups, which do not lead to the significant distortion of the trigonal-bipyramidal central atom coordination, are observed [11].
Sometimes the oxime ligand coordination method can be dependent on the nature of the aryl radicals at the antimony atom. For example, furfuraldoxime or 2-hydroxybenzaldoxime performs various structural functions in the derivatives of triphenyl- [8] and tri (o-tolyl) antimony [10] or triphenyl- and tris(5-bromo-2-methoxyphenyl)antimony [9], respectively.
Obviously, the oxidative-addition reactions of triarylantimony with oximes and the structure of the obtained products require further study.
The present work concerns the investigation of the interaction between tri(m-tolyl)- or tri(o-tolyl)antimony and 5-nitrofurfuradoxime in the presence of an oxidizing agent (hydrogen peroxide or t-butyl hydroperoxide) and the establishment of the product molecular structures.
Experimental
Synthesis of 6is(5-nitrofurfuraldoximato)tri(m-tolyl)antimony (1).
100 mg of tri(m-tolyl)antimony (0.25 mmol) and 79 mg (0.5 mmol) of 5-nitrofurfuraldoxime were dissolved in the mixture of diethyl ether (15 mL) and heptane (15 mL), then 28 mg of 30 % aqueous solution of hydrogen peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. After the solvent evaporation, the light-yellow crystals of 1 were obtained (m = 0.132 g (78 %), MP = 78 °C).
IR spectrum, v, cm-1: 3155, 3138, 3049, 2957, 2922, 2860, 1558, 1520, 1475, 1456, 1377, 1348, 1300, 1244, 1097, 1016, 970, 937, 810, 773, 739, 706, 689, 545, 505, 474, 426.
Synthesis of ¿M2-oxo-6is[(5-nitrofurfuraldoximato)tri(m-tolyl)antimony] (2).
a) 100 mg of tri(m-tolyl)antimony (0.25 mmol) and 39 mg (0.25 mmol) of 5-nitrofurfuraldoxime were dissolved in the mixture of diethyl ether (25 mL) and heptane (5 mL), then 28 mg of 30 % aqueous solution of hydrogen peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. After the solvent evaporation, the yellow crystals of 2 were obtained (m = 0.134 g (96 %), MP = 143 °C).
IR spectrum (v, cm-1): 3176, 3161, 3049, 2866, 2826, 1570, 1522, 1479, 1381, 1350, 1298, 1246, 1163, 1099, 1018, 966, 914, 860, 810, 775, 739, 689, 552, 484, 426.
b) 100 mg of tri(rn-tolyl)antimony (0.25 mmol) and 39 mg (0.25 mmol) of 5-nitrofurfuraldoxime were dissolved in the mixture of diethyl ether (15 mL) and heptane (15 mL), then 22 mg of 70 % aqueous solution of tert-butyl peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. After the solvent evaporation, the yellow crystals of 2 were obtained (m = 0.127 g (91 %), MP = 144 °C).
Synthesis of 6is(5-nitrofurfuraldoximato)tri(o-tolyl)antimony (3).
a) 100 mg of tri(o-tolyl)antimony (0.25 mmol) and 79 mg (0.5 mmol) of 5-nitrofurfuraldoxime were dissolved in diethyl ether (40 mL), then 28 mg of 30 % aqueous solution of hydrogen peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. When the solvent was evaporated, fine-crystalline precipitate was crystallized from benzene with the addition of heptane (5:1 vol.) to give light-yellow crystals of 3 (m = 0.139 g (83 %), MP = 154 °C, with destr.).
IR spectrum (v, cm-1): 1576, 1560, 1526, 1477, 1456, 1375, 1348, 1298, 1242, 1205, 1180, 1159, 1123, 1018, 964, 924, 864, 837, 808, 746, 737, 704, 683, 631, 582, 548, 507, 480, 436, 412.
b) 100 mg of tri(o-tolyl)antimony (0.25 mmol) and 79 mg (0.5 mmol) of 5-nitrofurfuraldoxime were dissolved in diethyl ether (40 mL), then 22 mg of 70 % aqueous solution of tert-butyl peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. When the solvent was evaporated, fine-crystalline precipitate was crystallized from benzene with the addition of heptane (5:1 vol.) to give light-yellow crystals of 3 (m = 0.139 g (83 %), MP = 154 °C, with destr.).
Synthesis of ^2-oxo-6is[(5-nitrofurfuraldoximato)tri(m-tolyl)antimony] (4).
a) 100 mg of tri(o-tolyl)antimony (0.25 mmol) and 39 mg (0.25 mmol) of 5-nitrofurfuraldoxime were dissolved in heptane (40 mL), then 28 mg of 30 % aqueous solution of hydrogen peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. After the solvent evaporation, the colorless crystals of 4 were obtained (m = 0.138 g (99 %), MP = 164 °C, with destr.).
IR spectrum (v, cm1): 1587, 1570, 1550, 1516, 1473, 1377, 1352, 1304, 1242, 1206, 1178, 1155, 1121, 1031, 1013, 982, 968, 943, 860, 822, 808, 798, 748, 723, 698, 674, 665, 542, 503, 471, 438, 409.
b) 100 mg of tri(o-tolyl)antimony (0.25 mmol) and 39 mg (0.25 mmol) of 5-nitrofurfuraldoxime were dissolved in heptane (40 mL), then 22 mg of 70 % aqueous solution of tert-butyl peroxide (0.25 mmol) were added. The mixture was kept for 24 hours at 20 °C. After the solvent evaporation, the yellow crystals of 4 were obtained (m = 0.138 g (99 %), MP = 164 °C, with destr.).
IR spectra of compounds 1-4 were recorded on a Shimadzu IRAffinity-1S FTIR spectrometer (pellets with KBr; 4000-400 cm-1).
X-ray diffraction analysis of crystalline substances 2, 4 was performed on Bruker D8 QUEST automatic four-circle diffractometer (Mo Ka- emission, X = 0.71073 A, graphite monochromator).
Data collection and editing, the refinement of unit cell parameters, and correction for absorption were carried out in SMART and SAINT-Plus software [10]. All calculations aimed at solving and refining the structures of 2, 4 were performed in SHELXL/PC software [11]. The structures of 2, 4 were
determined using direct methods and refined with LS method in the anisotropic approximation for non-hydrogen atoms. The selected crystallographic data and the structure refinement results are listed in Table 1. Selected bond lengths and bond angles are summarized in Table 2.
The full tables of atomic coordinates, bond lengths, and bond angles were deposited with the Cambridge Crystallographic Data Centre (CCDC 1048763, 1048167, 1048131 for compounds 2 and 4, respectively; [email protected]; http://www.ccdc.cam.ac.uk).
Table 1
Crystallographic data and the experimental and structure refinement parameters for compounds 2, 4
Parameter Value
2 4
Empirical formula Cs2H48N4O9Sb2 C26H24N2O4.5 Sb
Formula weight 1116.44 558.22
^ K 273.15 273.15
Crystal system monoclinic monoclinic
Space group P2j/c C2/c
a, A 22.472(2) 20.5292(11)
b, A 13.1397(11) 10.1119(6)
c, A 21.1657(18) 27.9617(15)
a, deg 90.00 90.00
P, deg 110.646(3) 91.075(2)
Y, deg 90.00 90.00
V, A3 5848.3(9) 5803.5(6)
Z 4 8
P(calcd.), g/cm3 1.268 1.278
|i, mm1 0.974 0.981
F(000) 2248.0 2248.0
9 Range of data collection, deg 6.5-38.12° 7-49.5°
Range of refraction indices -20 < h < 20, -12 < k < 12, -19 < l < 19 -24 < h < 19, -11 < k < 11, -32 < l < 31
Measured reflections 32451 9023
Independent reflections 4701 4648
Rint 0.0476 0.0428
Refinement variables 610 307
GOOF 1.117 1.078
R factors for F2 > 2ct(F2) R1 = 0.0738, wR2 = 0.2106 R1 = 0.0792, wR2 = 0.2043
R factors for all reflections R1 = 0.0906, wR2 = 0.2430 R1 = 0.1291, wR2 = 0.2323
Residual electron density (min/max), e/A3 1.54/-0.41 1.05/-0.47
Table 2
Selected bond lengths and bond angles in the structures of compounds 2, 4
Bond d, Â Angle ra, deg
2
Sb(1)-C(1) 2.156(17) O(1)Sb(1)O(2) 176.5(4)
Sb(1)-C(11) 2.107(19) C(11)Sb(1)C(1) 121.5(7)
Sb(1)-C(21) 2.051(16) C(21)Sb(1)C(11) 118.3(7)
Sb(1)-0(1) 1.971(9) C(1)Sb(1)C(21) 119.1(7)
Sb(1)-O(2) 2.130(10) N(1)O(2)Sb(1) 107.1(9)
0(2)-N(1) 1.409(17) O(2)N(1)C(35) 108.2(13)
O(6)-N(3) 1.332(17) Sb(1)O(1)Sb(2) 146.0(5)
N(1)-C(35) 1.267(19) N(3)O(6)Sb(2) 116.3(8)
N(3)-C(75) 1.206(17) O(6)N(3)C(75) 113.9(12)
Table 2 (end)
Bond d, Ä Angle ra, deg
Sb(2)-C(41) 2.119(15) C(61)Sb(2)C(51) 120.9(6)
Sb(2)-C(51) 2.088(13) C(51)Sb(2)C(41) 121.0(5)
Sb(2)-C(61) 2.092(14) C(41)Sb(2)C(61) 116.9(6)
Sb(2)-0(1) 1.975(8) O(1)Sb(1)C(11) 92.8(7)
Sb(2)-O(6) 2.127(9) O(1)Sb(1)C(21) 94.8(5)
Sb(1)-N(1) 2.88(2) O(1)Sb(2)C(61) 96.6(4)
Sb(2)-N(3) 2.97(1) O(1)Sb(2)C(41) 91.0(5)
4
Sb(1)-C(1) 2.097(10) O(1)Sb(1)O(2) 173.6(2)
Sb(1)-C(11) 2.116(16) C(11)Sb(1)C(1) 123.3(5)
Sb(1)-C(21) 2.107(17) C(21)Sb(1)C(1) 122.1(6)
Sb(1)-0(1) 1.960(8) C(11)Sb(1)C(21) 114.0(6)
Sb(1)-O(2) 2.193(8) N(1)O(2)Sb(1) 111.3(6)
0(2)-N(1) 1.335(11) O(4)N(2)C(34) 116.9(14)
O(5)-N(2) 1.187(14) Sb(1)O(1)Sb(2) 180.00(3)
N(1)-C(35) 1.302(13) O(5)N(2)C(34) 119.7(13)
N(2)-C(34) 1.395(16) O(1)Sb(1)C(11) 95.1(3)
Sb(1)-N(1) 2.95(1) O(1)Sb(1)C(21) 91.4(4)
Results and Discussion
We have studied the reactions of tri(m-tolyl) - and tri(o-tolyl)antimony with 5-nitrofurfuraloxime at various molar ratios in the presence of an oxidizing agent. It has been found that at molar ratio 1:2 of triarylantimony and 5-nitrofurfuraldoxime the product of the reactions, regardless of the nature of the oxidant, is bis(5-nitrofurfuraloximato)triarylantimony: m-Tol3Sb[ON=CHC4H2O(NO2-5)]2 (1) or o-Tol3Sb[ON=CHC4H2O(NO2-5)]2 (3):
Ar3Sb + 2 HON=CHC4H2O(NO2-5) + ROOH ^ Ar3Sb[ON=CHC4H2O(NO2-5)]2 + 2 ROH Ar = m-Tol, o-Tol; R = H, Bu-t
At the equimolar ratio of the reagents, in the presence of both hydrogen peroxide and tert-butyl hydroperoxide, ^-oxo-bis^-mtroforfuraldoxymato) tri(m-tolyl)antimony[m-Tol3SbON=CHC4H2O(NO2-5)]2O (2) or ^2-oxo-bis[(5-nitrofurfuraldoxymato)tri(o-tolyl) antimony] [o-Tol3SbON=CHC4H2O(NO2-5)]2O (4) is formed:
2 Ar3Sb + 2 HON=CHC4H2O(NO2-5) + 2 ROOH ^ [Ar3SbON=CHC4H2O(NO2-5)]2O + 2 ROH + H2O
Ar = m-Tol, o-Tol; R = H, Bu-t
Compounds 1-4 are crystalline substances, which are resistant to the effect of moisture and air oxygen and freely soluble in aromatic and aliphatic hydrocarbons.
The synthesized triarylantimony dioximates have been identified by infrared spectroscopy and X-ray diffraction analysis.
In the IR-spectrum of compounds 1-4 there are intensive absorption bands, which characterize nitro group vibrations. Thus, the absorption band due to NO2-group asymmetric vibrations is at 1520, 1522, 1526 h 1516 cm-1, while the band, corresponding to NO2-group symmetric vibrations appears at 1348, 1350, 1348 h 1352 cm-1 in the spectra of 1-4, respectively. The C-NO2 vibrations are characterized by the bands at 810, 810, 808 h 808 cm-1. In addition, there are bands at 426, 426, 436 h 438 cm-1, which have been attributed to the Sb-C(Ar) vibration of the C3-symmetric [12] SbC3 fragment. The characteristic bands at 1558-1587 cm-1 (C=N bonds), 964-970 cm-1 (N-O bonds) have also been found.
According to the X-ray diffraction analysis data, the antimony atoms in the molecules of compounds 2 and 4 have distorted trigonal-bipyramidal coordination with oxygen atoms in axial positions (Fig. 1-2). Molecule 4 is centrosymmetric. In binuclear molecules 2, 4 the Sb (1) and Sb (2) atoms are connected by the bridging oxygen atom, Sb(1)O(1)Sb(2) bond angles are equal to 146.0(3)° h 180.0(0)°, respectively. The oximate ligands in molecules 2, 4 are monodentate as in the case of ¡u2-oxo-bis [(furfuraloxymat)tri(o-tolyl) antimony] [10].
C47
Fig. 1. The structure of compound 2
Fig. 2. The structure of compound 4
The sums of CSbC bond angles are equal to 358.9(7)°, 358.8(6)° (2), 359.4(6)° (4), at that the values of the individual angles differ from the theoretical angle not more than by 6°. The Sb atoms are shifted from the correlated planes [C3] at 0.002 Á (1), 0.091, 0.098 Á (2), 0.052 Á (3). The axial OSbO angles are equal to 176.5(4)°, 176.1(3) (2), 173.6(2)° (4). The OSbC angles vary within the ranges 92.8(7)°-94.8(5)°, 91.0(5)°-96.6(4)° (2), 91.4(4)°-95.1(3)° (4).
The lengths of Sb-C bonds lie within the ranges of 2.051(16)-2.156(17) Á, 2.088(13)-2.119(15) Á (2), 2.097(10)-2.116(16) Á (4). The Sb-O bridging bond lengths in 2 (1.971(9), 1.975(8) Á) are longer in comparison with the same characteristic in 4 (1.960(8) Á), which correlates with the previously discovered pattern for the molecules with the similar structure: the closer the angle SbOSb is to linear, the shorter the Sb-O bond is [11]. The lengths of the Sb-O terminal bonds are 2.130 (10), 2.127 (9) Á (2), and 2.195 (8) Á (4). It should be noted that the values of angles for the antimony atom in molecule 4 are approximately equal to the corresponding values in the fragment of the molecule of ¡2-oxo-bis [(furfuraloxime)tri(o-tolyl)antimony], where the Sb-O-Sb fragment is linear, but the internuclear distances Sb-C and Sb-O in these molecules are different. Thus, the bonds Sb-O (1.9706 (3), 2.112 (6) Á [10]) in the latter compound are shorter than in 4, which can be explained by the presence of the nitro group in the furan ring of its oximate ligand.
In molecules 2, 4 the Sb-N distances between the Sb atom and N atoms of iminoxy groups [2.88(8), 2.97(1) Á (2), 2.95(1) Á (4)] are considerably less than the sum of Van der Waals radiuses of
the Sb and N atoms (3.8 Á [15]). Obviously, there is no correlation between the Sb-O bond lengths and strength of Sb- • N contacts. Thus, in the molecule of ^2-oxo-67's[(furfualoximatio)tri(o-tolyl)antimony], the distance Sb- • N (2.951(1) Á [10]) coincides with the comparable distance in 4. The decrease of the Sb-N distances does not result in the expected N-O bond lengthening [1.409(17), 1.332(17) Á (2), 1.335(11) Á (4)].
The structure organization of crystals 2, 4 is due to weak intermolecular 0--H hydrogen bonds between the oxygen atoms of nitro groups and the hydrogen atoms of methyl groups or aromatic rings, as well as due to C-H- • • n interactions.
Conclusions
The structure of the products of the reactions of tri(m-tolyl)- and tri(o-tolyl) antimony with 5-nitrofurfuraldoxime depends on the molar ratio of the reactants. Regardless of the nature of the oxidant, the reaction of triarylantimony with 5-nitrofurfuraloxime at molar ratio 1:2 leads to the formation of tritolylantimony dioxymates. At the stoichiometric ratio of the reagents the antimony-organic product with the bridging oxygen atom is formed.
The structure of molecules is determined by the aryl radical nature, thus, the p2-oxo-bis[(5-nitrofurfuraldoxymato)tri(m-tolyl)antimony molecule] has the angular structure of the central fragment, and the ^2-oxo-bis[(5-nitrofurfuraldoximato)tri(o-tolyl) antimony] molecule is centrosymmetric and has a linear structure. The oxime ligands are monodentate in both cases; they are bound to the antimony atom via the oxygen atom.
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Received 15 March 2017
УДК 546.863+546.865+547.152+547.53.024+548.312.5 DOI: 10.14529/chem170207
ОСОБЕННОСТИ ВЗАИМОДЕЙСТВИЯ ТРИ(МЕТА-ТОЛИЛ)СУРЬМЫ И ТРИ(ОРТО-ТОЛИЛ)СУРЬМЫ С 5-НИТРОФУРФУРАЛЬДОКСИМОМ. МОЛЕКУЛЯРНЫЕ СТРУКТУРЫ м2-ОКСО-БИС[(5-НИТРОФУРФУРАЛЬДОКСИМАТО)ТРИ(МЕТА-ТОЛИЛ)СУРЬМЫ] И М2-ОКСО-БИС[(5-НИТРОФУРФУРАЛЬДОКСИМАТО)ТРИ(ОРТО-ТОЛИЛ)СУРЬМЫ]
Е.В. Артемьева, М.С. Макерова, В.В. Шарутин, О.К. Шарутина
Южно-Уральский государственный университет, г. Челябинск
Взаимодействием три(мета-толил)сурьмы и три(орто-толил)сурьмы с 5-нитро-фурфуральдоксимом в присутствии окислителя (пероксида водорода или трет-бутилгидропероксида) синтезированы бис(5 -нитрофурфуральдоксимато)три(мета-толил)сурьма (1), f2-оксо -бис [(5 -нитрофурфуральдоксимато)три(мета-толил)сурьма] (2), бис(5-нитрофурфуральдоксимато)три(орто-толил)сурьма (3) и бис(5-нитро-фурфуральдоксимато)три(орто-толил)сурьма (4). Соединения 2, 4 охарактеризованы методом рентгеноструктурного анализа.
Ключевые слова: три(м-толил)сурьма, три(о-толил)сурьма, 5-нитрофурфур-альдоксим, третбутилгидропероксид, пероксид водорода, окисление, бис(5-нитрофурфуральдоксимато)три(м-толил)сурьма, ц2гоксо-бис[(5-нитрофурфур-
альдоксимато)три(м-толил)сурьма], бис(5-нитрофурфуральдоксимато)три(о-толил)-сурьма, ц2-оксо-бис[(5-нитрофурфуральдоксимато)три(о-толил)сурьма], молекулярные структуры, рентгеноструктурный анализ.
Литература
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Артемьева Екатерина Владимировна - аспирант химического факультета, ЮжноУральский государственный университет. 454080, г. Челябинск, пр. им. В.И. Ленина, 76. E-mail: [email protected].
Макерова Марина Сергеевна - аспирант химического факультета, Южно-Уральский государственный университет. 454080, г. Челябинск, пр. им. В.И. Ленина, 76. E-mail: [email protected].
Шарутин Владимир Викторович - доктор химических наук, профессор, старший научный сотрудник УНИД, Южно-Уральский государственный университет. 454080, г. Челябинск, пр. им. В.И. Ленина, 76. E-mail: [email protected].
Шарутина Ольга Константиновна - доктор химических наук, профессор, кафедра теоретической и прикладной химии, Южно-Уральский государственный университет. 454080, г. Челябинск, пр. им. В.И. Ленина, 76. E-mail: [email protected].
Поступила в редакцию 15 марта 2017 г.
ОБРАЗЕЦ ЦИТИРОВАНИЯ
The oxidative-addition reactions of tri(meta-tolyl)antimony and tri(ortho-tolyl)antimony with 5-nitrofurfuraldoxime in the presence of peroxides. The molecular structures of ^2-oxo-è/i[(5-nitrofurfur-aldoximato)tri(meta-tolyl)antimony] and ^2-oxo-fe[(5-nitrofurfuraldoximato)tri(ortho-tolyl)antimony] / E.V. Arte-meva, M.S. Makerova, V.V. Sharutin, O.K. Sharutina // Вестник ЮУрГУ. Серия «Химия». - 2017. - Т. 9, № 2. -С. 50-57. DOI: 10.14529/chem170207
FOR CITATION
Artemeva E.V., Makerova M.S., Sharutin V.V., Sharutina O.K. The Oxidative-Addition Reactions of Tri(meta-tolyl)antimony and Tri(ortho-tolyl)antimony with 5-Nitrofurfuraldoxime in the Presence of Peroxides. The Molecular Structures of ^2-Oxo-bis[(5-Nitrofurfur-aldoximato)tri(mefa-tolyl)antimony] and ^2-Oxo-fa's[(5-Nitrofurfuraldoximato)tri(ortho-tolyl)antimony]. Bulletin of the South Ural State University. Ser. Chemistry. 2017, vol. 9, no. 2, pp. 50-57. DOI: 10.14529/chem170207
