Adducts of tetraphenylstibium nitrate with nitric acid and of tetraphenylstibium acetate with acetic acid: Syntheses and structures

Article abstract of DOI:10.1134/S0036023608070206

The reactions of tetraphenylstibium nitrate with nitric acid and of tetraphenylstibium acetate with acetic acid yield adducts Ph ₄SbONO₂ · HNO₃ (I) and Ph ₄SbOC(O)CH₃ ? CHH₃COOH (II). According to X-ray diffraction data, the antimony atom in [Ph₄Sb] ⁺[O₂N-O?H?O-NO₂]^- has a tetrahedral coordination. The CSbC bond angles and Sb-C bond lengths vary within 108.04(6)°-109.75(4)° and 2.096(1)-2.098(1) A?, respectively. The anion includes the intermolecular hydrogen bond O(1)-H(1)?O(1)″: the O(1)-H(1), H(1)?O(1)″, and O(1)?O(1)″ distances are 0.91(4), 1.56(4), and 2.460(2) A?, respectively; and the OHO angle is 169(5)°. The nitrate groups are usually planar. Complex II also contains the intermolecular hydrogen bond with the following parameters: O(3)-H(3), 0.92 A?; H(3)?O(2), 1.68 A?; and O(3)?O(2) 2.594 A?; the O(2)H(3)O(3) angle is 172.1°. This H-bond noticeable changes the coordination polyhedron of the antimony atom compared to that in tetraphenylstibium acetate.

Full text of DOI:10.1134/S0036023608070206

ISSN 0036-0236, Russian Journal of Inorganic Chemistry, 2008, Vol. 53, No. 7, pp. 1110–1114. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © V.V. Sharutin, V.S. Senchurin, O.K. Sharutina, L.P. Panova, 2008, published in Zhurnal Neorganicheskoi Khimii, 2008, Vol. 53, No. 7, pp. 1194–1198.
PHYSICAL METHODS
OF INVESTIGATION
Adducts of Tetraphenylstibium Nitrate with Nitric Acid
and of Tetraphenylstibium Acetate
with Acetic Acid: Syntheses and Structures
V. V. Sharutin, V. S. Senchurin, O. K. Sharutina, and L. P. Panova
Blagoveshchensk State Pedagogical University, ul. Lenina 104, Blagoveshchensk, 675000 Russia
Received June 1, 2007
Abstract—The reactions of tetraphenylstibium nitrate with nitric acid and of tetraphenylstibium acetate with
acetic acid yield adducts Ph4SbONO2 · HNO3 (I) and Ph4SbOC(O)CH3 · CHH3COOH (II). According to X-ray
diffraction data, the antimony atom in [Ph4Sb]+[O2N–O···H···O–NO2]– has a tetrahedral coordination. The
CSbC bond angles and Sb–C bond lengths vary within 108.04(6)°–109.75(4)° and 2.096(1)–2.098(1) Å,
respectively. The anion includes the intermolecular hydrogen bond O(1)–H(1)···O(1)'': the O(1)–H(1),
H(1)···O(1)'', and O(1)···O(1)'' distances are 0.91(4), 1.56(4), and 2.460(2) Å, respectively; and the OHO angle
is 169(5)°. The nitrate groups are usually planar. Complex II also contains the intermolecular hydrogen bond
with the following parameters: O(3)–H(3), 0.92 Å; H(3)···O(2), 1.68 Å; and O(3)···O(2) 2.594 Å; the
O(2)H(3)O(3) angle is 172.1°. This H-bond noticeable changes the coordination polyhedron of the antimony
atom compared to that in tetraphenylstibium acetate.
DOI: 10.1134/S0036023608070206
Pentaarylstibium reacts with organic compounds
(HX) containing an active hydrogen atom, such as alco-
hols, phenols, β-diketones, and carboxylic and sulfonic
acids, to form, as a rule, products of the general formula
Ar4SbX; i.e., pentaarylstibium is selectively dearylated
to eliminate only one aryl group [1, 2]. The addition of
one mole of carboxylic acid to tetramethyl- or tetraphe-
nylstibium acylate results in the formation of stable
crystalline monomeric adducts R4SbOC(O)R' ·
HOC(O)R'' (R = CH3; R' = H, R'' = H; R' = CH3, R'' = CH3;
R' = CH3, R'' = C6H5; R'= C6H5, R''= C6H5; R = C6H5, R' =
CH3, R'' = CH3 [3]. Under severe conditions, pentaphe-
nylstibium and tetraphenylstibium bromide are dephe-
nylated to triphenylstibium dibromide [1].
For C24H21O6N2Sb anal. calcd. (%): C, 51.70; H,
3.54; N, 4.97.
Found (%): C, 51.89; H, 3.78; N, 5.04.
Synthesis of compound II. Tetraphenylstibium
acetate was recrystallized from 95% acetic acid. Uncol-
ored crystals with mp = 118°ë (112–113°ë [4]) were
obtained. IR, cm–1: 3059, 2988, 2923, 1733, 1634,
1582, 1570, 1479, 1431, 1395, 1364, 1335, 1295, 1275,
1067, 1019, 997, 738, 692, 469.
For C28H27O4Sb anal. calcd. (%): C, 61.20; H, 4.92.
Found (%): C, 61.01; H, 4.83.
IR spectra were recorded on an FSM1201 FTIR
spectrometer in KBr pellets.
Single-crystal X-ray diffraction analyses of com-
pounds I and II were carried out on a SMART-1000
CCD diffractometer (Bruker, MoKα radiation, graphite
monochromator).
Structures I and II were determined by a direct
method and refined by the least-squares method in the
anisotropic approximation for non-hydrogen atoms.
The positions of hydrogen atoms were calculated geo-
metrically and included into the refinement in the riding
model.
This work studies the reaction of tetraphenylstibium
nitrate with nitric acid and the structure of the resulting
adduct Ph4SbNO3 · HNO3 (I). We also refine the earlier
established [4] structure of the adduct of tetraphenyl-
stibium acetate with acetic acid, Ph4SbOC(O)CH3 ·
HOC(O)CH3 (II). The changes in the geometric param-
eters of Ph4Sbï molecules caused by the additional
acid molecule are analyzed.
The data were collected and edited and the unit cell
parameters were refined using the SMART and SAINT
Plus programs [5]. All calculations on structure deter-
mination and refinement were performed according to
the SHELXTL/PC programs [6].
Selected crystallographic data and the results of
refinement for structures I and II are given in Table 1.
EXPERIMENTAL
Synthesis of compound I. Tetraphenylstibium
nitrate was recrystallized from 10% nitric acid. Uncolored
crystals with mp = 102°ë were obtained. IR, cm–1: 3054,
2924, 1699, 1575, 1478, 1444, 1434, 1419, 1384, 1334,
1161, 1066, 1019, 999, 929, 800, 739, 688, 509, 463.
1110

ADDUCTS OF TETRAPHENYLSTIBIUM NITRATE WITH NITRIC ACID
1111
Table 1. Crystallographic data and details of the X-ray experiment and structure refinement for compounds I and II
Value
Parameter
I
II
FW
T, K
555.18
173(1)
549.25
296(2)
Crystal system
Space group
a, Å
Monoclinic
C2/c
18.133(1)
Monoclinic
P21/n
16.288(2)
b, Å
6.519(1)
10.334(1)
c, Å
19.095(1)
17.117(2)
β, deg
V, Å3
93.713(1)
2252.4(1)
117.113(2)
2567.1(5)
Z
ρ
4
4
calcd, g/cm3
1.637
1.269
1.421
1.105
µ, mm–1
F(000)
1112
1112
Crystal shape (size, mm)
θ range, deg
Intervals of reflection indices
Prism (0.35 × 0.30 × 0.15)
3.00–31.64
–26 ≤ h ≤ 20,
–8 ≤ k ≤ 9,
–28 ≤ l ≤ 28
9046
Prism (0.30 × 0.30 × 0.35)
2.34–30.04
–22 ≤ h ≤ 19,
–11 ≤ k ≤ 14,
–21 ≤ l ≤ 24
18216
Measured reflections
Independent reflections
Refinement variables
GOOF
R factors for F2 > 2σ(F2)
R factors for all reflections
3726 (Rint = 0.0288)
154
7156 (Rint = 0.0476)
303
1.039
0.869
R1 = 0.0219, wR2 = 0.0639
R1 = 0.0229, wR2 = 0.0648
–0.643/0.637
R1 = 0.0291, wR2 = 0.0569
R1 = 0.0507, wR2 = 0.0616
–0.454/0.366
Residual electron density (min/max),
e/Å3
atom in the [Ph4Sb]+ cation has an almost regular tetra-
hedral coordination. The CSbC bond angles and Sb–C
bond lengths vary in intervals of 108.04(6)°–
109.75(4)° and 2.096(1)–2.098(1) Å, respectively
(Table 3). The anion includes the intermolecular hydro-
gen bond O(1)–H(1)···O(1)'': the O(1)–H(1),
H(1)···O(1)'', and é(1)···é(1)'' distances are 0.91(4),
1.56(4), and 2.460(2) Å, respectively, and the OHO
angle is 169(5)°. The nitrate groups are planar, and the
ONO angles range from 118.05° to 124.66°. The
N−O(2,3) distances in complex I are equal to 1.218(1)
and 1.221(1)Å and correspond to the length of the delo-
The coordinates of atoms and temperature factors are
presented in Table 2. Selected bond lengths and bond
angles are listed in Table 3.
RESULTS AND DISCUSSION
Tetraphenylstibium nitrate (light yellow crystals
with mp = 186°ë), synthesized from pentaphenyl-
stibium and an equimolar amount of nitric acid in an
aqueous-acetate solution, was treated with excess nitric
acid. Regardless of the reaction conditions (tempera-
ture, solvent, time, acid concentration), the product was
the same compound Ph4SbNO3 · HNO3 (I) in the form
of colorless needle-like crystals with mp = 102°ë. The
IR spectrum of complex I, unlike the IR spectrum of
tetraphenylstibium nitrate, contains absorption bands at
1384 cm–1 (vs) and 800 cm–1 (w), which are character-
istic of the nitrate ion.
…
calized double bond N—O (1.22 Å [7]), and the
N−O(1) bond (1.316(1) Å) is substantially shorter than
the ordinary bond N–O in nitric acid (1.41 Å [7]).
In a molecule of compound III, the antimony atom
has a distorted trigonal bipyramidal coordination [8].
The CaxSbCeq, OSbCeq, CeqSbCeq, and OSbCax bond
angles in molecules a and b in a crystal of compound
III are as follows: 100.0°–100.2° (100.2°), 78.1°–
81.3° (79.8°), 114.7°–119.6° (350.8°), and 178.4° and
96.3°–100.3° (98.7°), 74.5°–85.1° (81.53°), 114.4°–
According to the X-ray diffraction data, the compo-
sition of adduct I can be presented by the formula
[Ph4Sb]+[O2N–O···H···O–NO2]– (Fig. 1). The antimony
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 53 No. 7 2008

1112
SHARUTIN et al.
Table 2. Coordinates of atoms (×104) and their isotropic equiv- Table 3. Bond lengths (d) and bond angles (ω) in structures
alent temperature parameters (×103) in structures I and II
I and II
Ueq, Å2
Atom
x
y
z
Bond
d, Å
Angle
ω, deg
I
I
Sb
10000
3069.4(1) 7500
17.35(2)
32.5(2)
42(3)
Sb–C(11)
Sb–C(11)'
Sb–C(21)
Sb–C(21)'
O(1)–N
2.0964(10) C(11)SbC(11)'
2.0964(10) C(11)SbC(21)
2.0985(10) C(11)'SbC(21)
2.0985(10) C(11)SbC(21)'
1.3158(14) C(11)'SbC(21)'
108.04(6)
108.58(4)
109.75(4)
109.75(4)
108.58(4)
112.04(6)
103(3)
O(1)
H(1)
O(2)
O(3)
N
C(11) 9066(1)
C(12) 8899(1)
C(13) 8291(1)
C(14) 7867(1)
C(15) 8039(1)
C(16) 8636(1)
C(21) 9902(1)
C(22) 10468(1)
C(23) 10390(1)
C(24) 9747(1)
C(25) 9189(1)
C(26) 9262(1)
7052(1)
7410(30)
6874(1)
7862(1)
7274(1)
3915(2) 5003(1)
2940(50) 5050(30)
6755(2) 5555(1)
4983(2) 5812(1)
5280(2) 5479(1)
1180(2) 7365(1)
–124(2) 7914(1)
–1421(2) 7828(1)
–1446(2) 7193(1)
–157(2) 6648(1)
1182(2) 6732(1)
4869(2) 8401(1)
6211(2) 8623(1)
7406(2) 9217(1)
7260(2) 9577(1)
5912(2) 9356(1)
4703(2) 8768(1)
II
43.7(3)
46.0(3)
27.5(2)
19.0(2)
23.0(2)
26.0(2)
25.8(2)
24.8(2)
21.6(2)
20.1(2)
24.8(2)
30.0(3)
30.5(3)
29.1(2)
23.2(2)
O(1)–H(1)
O(2)–N
0.91(4)
C(21)SbC(21)'
1.2179(15) NO(1)H(1)
1.2207(14) O(2)NO(3)
O(3)–N
124.66(12)
117.29(11)
118.05(11)
C(11)–C(16) 1.3941(14) O(2)NO(1)
C(11)–C(12) 1.3986(15) O(3)NO(1)
C(12)–C(13) 1.3902(16) C(16)C(11)C(12) 120.91(9)
C(13)–C(14) 1.3943(17) C(16)C(11)Sb
120.53(7)
118.53(7)
C(14)–C(15) 1.3885(17) C(12)C(11)Sb
II
Sb–C(31)
Sb–C(11)
Sb–C(41)
Sb–C(21)
Sb–O(1)
2.105(2)
2.118(1)
2.119(1)
2.166(2)
2.291(1)
1.279(2)
1.232(2)
1.313(2)
1.181(2)
1.509(3)
1.469(3)
C(31)SbC(11)
C(31)SbC(41)
C(11)SbC(41)
C(31)SbC(21)
C(11)SbC(21)
C(41)SbC(21)
C(31)SbO(1)
C(11)SbO(1)
C(41)SbO(1)
C(21)SbO(1)
O(2)C(1)O(1)
O(2)C(1)C(2)
O(1)C(1)C(2)
O(4)C(3)O(3)
O(4)C(3)C(4)
O(3)C(3)C(4)
115.79(5)
124.07(6)
116.17(6)
96.15(6)
95.83(6)
97.83(5)
83.05(5)
81.47(5)
85.43(5)
176.47(4)
124.4(2)
121.5(2)
114.0(2)
121.4(2)
122.1(2)
116.6(2)
Sb
4844.85(6) 8225.0(1) 1819.78(5)
40.27(3)
56.3(3)
74.0(4)
94.5(5)
124.3(7)
63.3(5)
151(1)
77.1(6)
130(1)
42.8(4)
56.0(5)
71.8(6)
70.7(6)
64.8(5)
52.8(4)
43.3(4)
52.4(4)
63.4(5)
70.5(6)
69.5(6)
57.0(5)
44.4(4)
55.7(5)
69.6(5)
78.4(6)
79.5(6)
61.4(5)
43.7(4)
54.3(5)
64.6(5)
68.4(6)
67.6(5)
55.7(5)
110
O(1)
O(2)
O(3)
O(4)
C(1)
C(2)
C(3)
C(4)
3408(1)
3684(1)
3219(1)
3582(1)
3171(1)
2190(1)
3753(1)
4573(2)
7845(1) 1703(1)
8884(1) 2934(1)
9401(2) 4163(1)
8898(2) 5515(1)
8277(2) 2271(1)
7960(4) 2071(1)
8846(2) 4916(1)
8174(3) 4972(2)
7131(1)
7351(2)
6657(2) –716(1)
5722(2) –895(1)
5478(2) –305(1)
O(1)–C(1)
O(2)–C(1)
O(3)–C(3)
O(4)–C(3)
C(1)–C(2)
C(3)–C(4)
C(11) 4294(1)
C(12) 4640(1)
C(13) 4306(1)
C(14) 3650(1)
C(15) 3318(1)
C(16) 3630(1)
C(21) 6164(1)
C(22) 6349(1)
C(23) 7143(1)
C(24) 7751(1)
C(25) 7573(1)
C(26) 6791(1)
C(31) 4419(1)
C(32) 4871(1)
C(33) 4607(1)
C(34) 3907(1)
C(35) 3465(1)
C(36) 3716(1)
C(41) 5337(1)
C(42) 6143(1)
C(43) 6479(1)
C(44) 6033(1)
C(45) 5238(1)
C(46) 4883(1)
645(1)
54(1)
C(11)–C(12) 1.383(2)
C(11)–C(16) 1.384(2)
C(12)–C(13) 1.376(2)
C(13)–C(14) 1.368(3)
C(14)–C(15) 1.370(3)
6184(2)
458(1)
8603(2) 1844(1)
9771(2) 1564(1)
9925(2) 1465(1)
8924(2) 1641(1)
7755(2) 1919(1)
7596(2) 2021(1)
10168(2) 1692(1)
11035(2) 2367(1)
12316(2) 2258(1)
12727(2) 1481(1)
Symmetry transformations:' –x + 2, y, –z + 3/2; " –x + 3/2, –y + 1/2,
–z + 1.
119.8° (353.3°), and 170.7° respectively (the average
values of the angles or the sums of the corresponding
angles are given in parentheses). The average Sb–Ceq
bond lengths (2.108 (a) and 2.104 (b) Å) are less than
the Sb–C axial bonds (2.138 and 2.134 Å, respectively).
The Sb–O distances are 2.548 Å (a) and 2.493 Å (b).
11874(2)
10597(2)
816(1)
912(1)
7157(2) 3004(1)
7551(2) 3721(1)
6849(2) 4495(1)
5766(2) 4550(1)
5370(2) 3842(1)
6070(2) 3066(1)
9240(20) 3693(12)
The nitrate groups in both compounds III and I are
planar; the angles at the nitrogen atoms do not virtually
differ from a theoretical value of 120° (118.0°–121.6°,
118.0°–121.3° in III, a and b). The N–O bond lengths in
H(3)
3330(12)
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 53 No. 7 2008

ADDUCTS OF TETRAPHENYLSTIBIUM NITRATE WITH NITRIC ACID
1113
C(25)
C(24)
O(2)
C(13)
C(11)
C(26)
C(12)
N
C(14)
O(1)
C(21)
C(15)
C(16)
C(23)
O(3)
H(1)
C(22)
C(11)'
C(21)''
O(1)''
Fig. 1. Structure of complex I.
C(2)
C(35)
O(3)
O(4)
C(34)
C(1)
O(2)
C(15)
O(1)
C(33)
C(36)
C(14)
C(3)
C(4)
C(16)
C(31)
C(13)
C(32)
C(11)
C(46)
Sb
C(12)
C(41)
C(42)
C(45)
C(44)
C(22)
C(21)
C(23)
C(24)
C(43)
C(26)
C(25)
Fig. 2. Structure of complex II.
compound III (a and b) are 1.278, 1.249, 1.225 Å and implemented in complex I, because the introduction of
1.269, 1.241, and 1.226 Å, respectively. The longer an acid molecule enhances the efficient delocalization
bond is observed with the oxygen atom that is coordi- of the negative charge and the stability of the anion.
nated to the antimony atom. The observed values sug-
We refined the structure of complex II, in which the
gest the electron density distribution in the nitrate
group like that in the nitrate anion.
carbonyl oxygen atom of the acetate ligand is hydro-
gen-bonded to the hydroxy group of the acetic acid
Thus, the tendency of the central atom in compound molecule (Fig. 2). The presence of the rather stable
III to acquire the tetrahedral coordination mode is intermolecular hydrogen bond (O(3)–H 0.92, ç···O(2)
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 53 No. 7 2008

1114
SHARUTIN et al.
1.68, é(3)···O(2) 2.594 Å, O(2)HO(3) angle 172.1°)
noticeably changes the geometric parameters of com-
plex II (Table 3) compared to the same characteristics
of tetraphenylstibium acetate (IV). For example, the
Sb–O bond (2.291 Å) in complex II is much longer than
that in compound IV (2.234 Å). The Sb···O=C distance
in compound I is 3.307 Å, whereas this distance in IV
is 2.594 Å. On the contrary, the axial and equatorial
Sb−C bonds (2.166 Å and 2.105, 2.118, and 2.119 Å) in
compound II are much shorter than those in IV (2.179 Å
and 2.136, 2.138, and 2.143 Å). The coordination poly-
hedron of the antimony atom in compound II is less
distorted (the CSbO axial angle is 176.47°; the CSbC
equatorial angles are 115.79°, 116.17°, and 124.07°)
than that in compound IV (the corresponding angles are
170.04°, 102.15°, 102.92°, and 152.62°) because the
strong intramolecular Sb···O=C interaction is absent.
REFERENCES
1. K. A. Kocheshkov, A. P. Skoldinov, and N. N. Zemlyan-
skii, The Methods of Organoelement Chemistry: Anti-
mony and Bismuth (Nauka, Moscow, 1976) [in Russian].
2. O. K. Sharutina, Doctoral Dissertation in Chemistry
(Favorsky Inst. of Chemistry, Irkutsk, 2001).
3. H. Schmidbaur and K. H. Mitschke, Angew. Chem. 83,
149 (1971).
4. S. P. Bone and D. B. Sowerby, Phosphorus, Sulfur, Sili-
con Relat. Elem. 45 (1–2), 23 (1989).
5. SMART and SAINT-Plus. Versions 5.0. Data Collection
and Processing Software for the SMART System (Bruker
AXS, Madison (WI, USA), 1998).
6. SHELXTL/PC. Versions 5.10. An Integrated System for
Solving, Refining and Displaying Crystal Structures From
Diffraction Data (Bruker AXS, Madison (WI, USA),
1998).
In adduct II, the C–O distance in the acetate frag-
ment is 1.279 Å and coincides with that in IV. The ë=é
bond in the carbonyl group in II (1.232 Å) is shorter
than that in IV (1.266 Å), which correlates with a less
stable Sb···O=C contact. The C(3)–O(3) and C(3)–O(4)
distances in an acetic acid molecule are 1.313 and 1.181 Å,
respectively.
7. F. H. Allen, O. Kennard, D. G. Watson, et al., J. Chem.
Soc. Perkin Trans. II, No. 12, S1 (1987).
8. V. V. Sharutin, O. K. Sharutina, L. P. Panova, et al., Zh.
Obshch. Khim. 72 (1), 45 (2002).
9. S. P. Bone and D. B. Sowerby, Phosphorus, Sulfur, Sili-
con. Relat. Elem. 45 (1–2), 23 (1989).
In tetraphenylstibium carboxylates Ph4SbOC(O)R,
the distance between the antimony atom and carbonyl
oxygen atom (which are not formally linked to each
other) was found to be 2.594–3.509 Å [9–21] (the sum
of the van der Waals radii of the antimony and oxygen
atoms is 3.70 Å [22]), and in IV this value is minimum
(2.594 Å) [9]. The strength of the Sb···O=C intramolec-
ular contact, associated with the donor-acceptor inter-
action, is obviously due to many factors, for instance,
the electron-donating ability of the oxygen atom of the
carbonyl group. This ability, in turn, is caused by the
nature of the organic radical R. A considerable weaken-
ing of the Sb···O=C contact in II compared to that in IV
indicates that intermolecular interactions involving the
carbonyl oxygen atom play an important role in the for-
mation of compound IV.
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in the Ph4Sbï · çï adduct (X = NO3 or OC(O)CH3)
affects the geometric parameters of the X fragments
and also substantially changes the coordination polyhe-
dron of the antimony atom.
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ACKNOWLEDGMENTS
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Zhurn. Obshch. Khimii 74 (2), 234 (2004).
The authors are grateful to A.V. Gerasimenko and
M.A. Pushilin (Institute of Chemistry, Far East Divi-
sion, Russian Academy of Sciences, Vladivostok) for
X-ray diffraction analyses of complexes I and II.
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Koord. Khim. 28 (5), 356 (2002).
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RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 53 No. 7 2008