Inner complex compounds of dioxomolybdenum(VI) with o-oxyazomethines, derivatives of substituted salicylaldehydes and tris(hydroxymethyl)aminomethane. crystal structures of two complexes [MoO(L)] · CH3OH; L = Z-substituted salicylalimines, Z =

Article abstract of DOI:10.1134/S1070328413080010

Ten new dioxomolybdenum(VI) compounds with o-oxyazomethines, derivatives of substituted salicylaldehydes (I-X) and tris(hydroxymethyl)aminomethane, are synthesized. The structures of two of them, [MoO₂(L)] · CH₃OH; L = Z-substituted

Full text of DOI:10.1134/S1070328413080010

ISSN 1070ꢀ3284, Russian Journal of Coordination Chemistry, 2013, Vol. 39, No. 8, pp. 553–559. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © V.L. Abramenko, A.V. Churakov, V.S. Sergienko, Yu.N. Mikhailov, M.D. Surazhskaya, 2013, published in Koordinatsionnaya Khimiya, 2013, Vol. 39,
No. 8, pp. 456–462.
Inner Complex Compounds of Dioxomolybdenum(VI)
with oꢀOxyazomethines, Derivatives of Substituted Salicylaldehydes
and Tris(hydroxymethyl)aminomethane. Crystal Structures
of Two Complexes [MoO(L)] · CH3OH; L = ZꢀSubstituted
Salicylalimines, Z = 3ꢀNO2 and 3ꢀOCH3
V. L. Abramenkoa, A. V. Churakovb, V. S. Sergienkoa, *, Yu. N. Mikhailovb, and M. D. Surazhskayab
a East Ukrainian State University, Lugansk, Ukraine
b Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences,
Leninskii pr. 31, Moscow, 119991 Russia
*eꢀmail: sergienko@igic.ras.ru
Received January 16, 2013
Abstract—Ten new dioxomolybdenum(VI) compounds with
salicylaldehydes (I–X) and tris(hydroxymethyl)aminomethane, are synthesized. The structures of two of
them, [MoO2(L)] · CH3OH; L = Zꢀsubstituted salicylalimines, Z = 3ꢀNO2 (IV) and 3ꢀOCH3 ( ), are deterꢀ
have similar structures and geometric parameters.
oꢀoxyazomethines, derivatives of substituted
V
mined by Xꢀray diffraction analysis. Compounds IV and
V
The Mo atoms are coordinated through the octahedral mode by two oxo ligands in the cis positions to each
other, two O atoms, one N atom of the tridentate bis(chelating) ligand L, and the O atom of the MeOH molꢀ
ecule.
DOI: 10.1134/S1070328413080010
INTRODUCTION
Salicylalimines ( ꢀoxyazomethines, Schiff bases)
represent a classical example of prototropic tauꢀ
tometic systems for which two tautomers can theoretꢀ
c; scheme). One of them can be presented in two resoꢀ
nance forms (b, c; scheme), which makes it possible to
obtain from them complexes of different types and
structures: adducts or molecular complexes, and inner
o
ically exist in the crystalline state and in solution (a, b, complex compounds [1, 2].
O−
O
O
H
N
H
H
N
N+
R
R
R
Z
Z
Z
а
b
c
Quinoid (
b
) and zwitterionic (c) resonance forms of keto–amine tautomer
Phenol–imine tautomer (а)
Scheme.
The introduction of additional donor centers or function and is coordinated through the oxygen atom
functional groups into amine fragment R extends of the deprotonated phenolic OH group and the
coordination possibilities of salicylalimines. In particꢀ azomethine nitrogen atom or through two oxygen
ular, salicylalcoholimines (H2L), where R is atoms of the phenolic and alcoholic hydroxy groups
(СН2)nОН, form with transition metal salts several and the nitrogen atom of doubly deprotonated anion
types of inner complex compounds of the monomeric L2–. The data of elemental analysis, IR and NMR
[1–5] and diꢀ and polymeric structures [6, 7]. In these spectroscopy [8–11], and Xꢀray diffraction analysis
structures, the ligand exhibits the biꢀ or tridentate [12] showed that the solvated dioxomolybdenum(VI)
553

554
ABRAMENKO et al.
complexes with substituted salicylalmonoethanolꢀ ture
amines MoO2L CH3OH were monomeric. Continuꢀ rier syntheses and refined isotropically. Other hydroꢀ
ing the systematic study of the complex formation of gen atoms in structure (and H(Me) atoms in IV
V were objectively localized from difference Fouꢀ
⋅
V
)
dioxomolybdenum(VI) with salicylalcoholimines and were specified in the calculated positions and refined
the direct proof of the complexes formed, we syntheꢀ by the riding model.
sized ten inner complex compounds of Mo(VI) with a
Selected interatomic distances and bond angles are
series of
hyde (Z = H (
3ꢀOCH3 ), 3,5ꢀCl2
3ꢀOCH3ꢀ5ꢀNO2 (VIII) and
(Z = 5,6ꢀcycloꢀC4H4 (IX
thyl)aminomethane (R = C(CH2OH)3). The strucꢀ
оꢀoxyazomethines, derivatives of salicylaldeꢀ
given in Table 3. The hydrogen bond parameters are
listed in Table 4. The full tables of atomic coordinates,
bond lengths, and bond angles for compounds IV
I
), 5ꢀBr (II), 5ꢀNO2 (III), 3ꢀNO2 (IV),
VI), 3,5ꢀBr2 VII), and
ꢀoxynaphthoic aldehyde
) and tris(hydroxymeꢀ
(
V
(
(
β
and
V were deposited with the Cambridge Crystalloꢀ
,
X
graphic Data Centre (nos. 917591 and 917592, respecꢀ
tively; deposit@ccdc.cam.ac.uk; http://www.ccdc.
cam.ac.uk/data_request/cif).
tures of compounds IV and
V were determined by
Xꢀray diffraction analysis.
RESULTS AND DISCUSSION
EXPERIMENTAL
The Xꢀray diffraction results for free оꢀoxyazomeꢀ
Synthesis of I–X. Azomethines were synthesized by
refluxing for 0.5 h of equimolar amounts of the correꢀ
sponding aldehydes and amine NH2C(CH2OH)3 in
alcohol followed by keeping the solution in a refrigerꢀ
ator for 24 h. The crystals formed were filtered off,
washed with cold alcohol, and dried first on the filter
and then over СаСl2. The purity of the substances was
monitored chromatographically.
thines and derivatives of salicylaldehydes and
tris(hydroxymethyl)aminomethane show that in
the crystalline state these azomethines exist predomiꢀ
nantly in the quinoid form [14–20], whereas the zwitꢀ
terionic form is rarely met [20]. For example, the
N
⎯
H bond length is 1.01 Å and the
Н
⋅⋅⋅
О distance is
1.77 Å in an ꢀsalicylideneaminoꢀ1ꢀtris(hydroxymeꢀ
N
thyl)methane molecule, which unambiguously indiꢀ
cates the localization of the hydrogen atom on the
nitrogen atom [14]. At the same time, the nature of
substituents in both the aldehyde and amine fragments
affects the stabilization of a specific tautomeric form
of salicylalimines in the crystalline state. In this
respect, the Xꢀray diffraction data are convincing for
salicylalimines, condensation products of substituted
Zꢀsalicylaldehyde and tris(hydroxymethyl)amiꢀ
The complexes were synthesized by refluxing soluꢀ
tions of equimolar amounts of molybdenyl acetylaceꢀ
tonate and azomethines in methanol, distilling off a
portion of the solvent, and cooling the solutions to
0
°
С
. The yields of the complexes ranged from 80 to
90% of the theoretical value. Compounds VIII and
with dimethylformamide (DMF), MoO2L DMF,
were synthesized by the recrystallization of complexes
MoO2L CH3OH in methanol with the addition of 1–
2 mL of dimethylformamide.
X
⋅
⋅
nomethane [20]. Zwitterionic form
c is detected in the
crystalline state for azomethine with the substituent
Z = 3ꢀOEt in the aldehyde fragment. In the case of
On heating to 140–150°С complexes I–X are desꢀ
olvated and on further heating melt with decomposiꢀ
tion.
Z = 5ꢀNO2, the quinoid form b is observed as a result
of a resonance between the zwitterionic form and nitro
group. Unsubstituted (Z = H) salicylideneꢀ2ꢀ(1ꢀ
hydroxybutyl)imine crystallizes in the phenol–imine
The elemental analysis data, melting points, and
IR spectra of complexes I–X (IKSꢀ29 spectrophoꢀ
tometer, suspension in Nujol) are given in Table 1.
form
a [20].
The IR spectra of complexes
I–X (Table 1) demonꢀ
Xꢀray diffraction analysis. The main crystalloꢀ
graphic characteristics and refinement parameters for
strate the following features. Broad diffuse absorption
bands of alcoholic groups are observed at 3000–
3600 cm–1, which (along with the elemental analysis
data) suggests the participation of only one of three
OH groups of the amine fragment in coordination. It
is most likely that the ligands are transformed into the
benzoid tautomeric form followed by the deprotonaꢀ
tion of one of the alcohol groups and fiveꢀmembered
metallocycle closure. The stretching vibrations of the
structures IV and
mental data were obtained on Bruker SMART
APEX II (for IV) and EnrafꢀNonius CADꢀ4 (for
diffractometers ( Mo radiation, = 0.7073 Å,
graphite monochromator, scan mode). An absorpꢀ
V are listed in Table 2. The experiꢀ
V)
λ
K
λ
α
ω
tion correction was applied empirically by equivalent
reflections.
Structures IV and
V were determined by direct C=N azomethine bond appear as intense bands
methods and refined by least squares for F2 in the fullꢀ at 1620–1630 cm–1 as in the spectra of the dioxomoꢀ
matrix anisotropic approximation for nonꢀhydrogen lybdenum(VI) complexes with salicylidenemonoethaꢀ
atoms [13]. The hydrogen atoms in structure IV nolamines [12]. The absorption bands at 500–590 cm–1
(except for the hydrogen atoms of the methyl group) can be assigned to stretching vibrations of the Мо–OL
and the H(1–3) atoms of the hydroxy groups in strucꢀ bond. The strong bands at 900–950 cm–1 are attribꢀ
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
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INNER COMPLEX COMPOUNDS OF DIOXOMOLYBDENUM(VI)
555
(а)
O(5)
C(11)
C(6)
C(8)
C(7)
C(1)
C(5)
C(10)
N(1)
C(9)
O(1)
C(4)
C(2)
O(6)
O(4)
Mo(1)
O(2)
O(3)
C(3)
O(7)
N(2)
O(8)
O(9)
C(12)
(b)
O(5)
C(6)
C(5)
C(11)
C(7)
O(6)
C(8)
C(1)
C(4)
N(1)
C(10)
C(3)
O(8)
C(2)
O(1)
C(9)
O(4)
O(3)
Mo(1)
C(13)
C(12)
O(7)
O(2)
Structures of complex molecules (a) IV and (b) V. The intramolecular hydrogen bond is shown by dashed line.
of the metal atom with ligand L2– in structures IV and
uted to symmetric and antisymmetric stretching vibraꢀ
tions of the cis МоО2 group [13].
ꢀ
V
, two condensed metallocycles are closed: the sixꢀ
membered cycle Mo, O(3), C(2), C(1), C(7), N(1)
) and fiveꢀmembered metallocycle Мо, О(4), С(9),
(8), N(1) ( ). The conformation of chelate in
According to the Xꢀray diffraction data, complexes IV
and (figure) have the monomeric octahedral strucꢀ
(А
V
С
B
A
ture. The structures of the complex molecules of both
structure IV is a flattened sofa (the O(3) atom is
declined by 0.153 Å from the plane of other five coplaꢀ
compounds and analogous geometric parameters
2+
МоО2
are similar. The
dioxo group is in the cis conꢀ
nar ( 0.003–0.011 Å) atoms). The cycle in structure
V
figuration typical of complexes of d0 metals of
Groups V–VII in the highest oxidation state [21, 22].
The O(7) atoms of the solvate methanol molecules and
the N(1) atoms of tridentate bis(chelate) ligands L2–
are in the trans positions to the oxo ligands in strucꢀ
has a substantially nonplanar conformation with the
deviation of the Mo and O(3) atoms from the plane of
other four coplanar ( 0.017–0.038 Å) atoms by 0.317
and 0.199 Å, respectively. The fiveꢀmembered metalꢀ
locycles
B in structures IV and V have the same skewed
tures IV and V. The deprotonated O(3) atoms of the
oxyazomethine fragment and O(4)(ethanolamine) are
arranged in the trans positions to each other and in the
conformation with the deviation of the О(4) and С(9)
atoms from the plane of the Mo, N(1), and C(8) atoms
cis positions to the oxo ligands. For the coordination by –0.456, 0.127 Å in IV and –0.183, 0.443 Å in V,
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
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556
ABRAMENKO et al.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
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INNER COMPLEX COMPOUNDS OF DIOXOMOLYBDENUM(VI)
557
Table 2. Main crystallographic and experimental characteristics of compounds IV and
V
Value
Parameter
IV
V
Crystal system
Space group
Monoclinic
21/
Monoclinic
P
n
P21/c
a
, Å
, Å
6.9228(3)
25.0045(11)
8.4795(4)
100.384(1)
1443.77(11)
150(2)
10.883(2)
9.098(3)
15.801(4)
101.30(2)
1534.2(7)
100(2)
4
b
c
, Å
β
, deg
V
, Å3
Temperature, K
Z
4
M
428.21
413.23
1.789
ρcalcd, g/cm3
1.970
F(000)
864
840
μ, mm
0.964
0.897
θmax, deg
Sample size, mm
Rint
27.00
25.98
0.40
×
0.10
×
0.02
0.40
×
0.30
× 0.10
0.0253
0.0313
Tmax
,
Tmin
0.9810, 0.6991
0.9156, 0.7155
Total number of reflections
11319
11590
Number of independent reflections
3142
2893
3006
2723
Number of reflections,
I
> 2σ(I)
Number of refined parameters
270
222
R
R
(
I
> 2
σ
(
I
))
R
1 = 0.0221, wR2 = 0.0541
1 = 0.0251, wR2 = 0.0556
1.039
R
1 = 0.0181, wR2 = 0.0460
1 = 0.0226, wR2 = 0.0474
1.048
(all data)
R
R
Goodnessꢀofꢀfit
/Å3
ρmax
,
ρmin
,
e
0.464, –0.446
0.393, –0.280
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
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558
ABRAMENKO et al.
respectively. The phenylene ring C(1–6) (
gated with the sixꢀmembered chelate is planar with
an accuracy of 0.004–0.016 and 0.005–0.016 Å in
structures IV and , respectively. The inflection angles
along the C(1)–C(2) line are 4.0 and 11.9 in strucꢀ
tures IV and , respectively.
C) conjuꢀ
Table 3. Selected bond lengths (
d
) and bond angles ( ) for
ω
compounds IV and
V
A
IV
V
V
Bond
d
, Å
°
°
Mo(1)–O(1)
Mo(1)–O(2)
Mo(1)–O(4)
Mo(1)–O(3)
Mo(1)–N(1)
Mo(1)–O(7)
N(1)–C(7)
N(1)–C(8)
N(2)–O(9)
N(2)–O(8)
N(2)–C(3)
O(3)–C(2)
O(4)–C(9)
O(5)–C(11)
O(6)–C(10)
O(7)–C(12)
1.7025(15)
1.7053(15)
1.9259(13)
1.9780(14)
2.2795(16)
2.3021(16)
1.280(2)
1.497(2)
1.225(2)
1.230(2)
1.465(3)
1.6997(13)
1.7055(13)
1.9550(13)
1.9649(13)
2.2985(15)
2.3054(14)
1.288(2)
1.481(2)
1.339(2)
1.419(2)
1.424(2)
V
The lengths of the Мо=О(1,2) multiple bonds
1.704 0.001 Å in IV 1.703 0.003 Å in ) fall in the
(
,
V
typical range of values from 1.66 to 1.77 Å (Table 5 in
[23, 24]).
The bonds in the trans positions to Мо=О(oxo) are
usually elongated strongly due to the random transꢀ
effect of the multiply bonded oxo ligands. Nevertheꢀ
less, the Мо–N(1) bonds in IV and
V (2.280 and
1.313(2)
1.431(2)
1.425(2)
1.427(3)
1.422(2)
1.427(2)
1.366(2)
1.436(2)
2.299 Å, respectively), as a similar bond in the close in
composition structure [MoO2(L)]
⋅
CH3OH (XI),
where L2 is 3,5ꢀdichlorosalicylidene monoethanolimꢀ
inate; R,R is 3,5ꢀCl2 (Mo–N 2.277 Å), are among the
shortest (in other words, least weakened) bonds
according to literature data (for example, Мо–Ntrans
2.308–2.486 Å for 12 structures of the monomeric
1.420(3)
1.403(2)
IV
V
Angle
ω
, deg
O(1)Mo(1)O(2)
O(1)Mo(1)O(4)
O(2)Mo(1)O(4)
O(1)Mo(1)O(3)
O(2)Mo(1)O(3)
O(4)Mo(1)O(3)
O(1)Mo(1)N(1)
O(2)Mo(1)N(1)
O(4)Mo(1)N(1)
O(3)Mo(1)N(1)
O(1)Mo(1)O(7)
O(2)Mo(1)O(7)
O(4)Mo(1)O(7)
O(3)Mo(1)O(7)
N(1)Mo(1)O(7)
C(7)N(1)C(8)
C(7)N(1)Mo(1)
C(8)N(1)Mo(1)
O(9)N(2)O(8)
O(9)N(2)C(3)
O(8)N(2)C(3)
C(2)O(3)Mo(1)
C(9)O(4)Mo(1)
C(12)O(7)Mo(1)
O(3)C(2)C(3)
O(3)C(2)C(1)
C(4)C(3)N(2)
C(2)C(3)N(2)
N(1)C(7)C(1)
N(1)C(8)C(9)
N(1)C(8)C(10)
N(1)C(8)C(11)
O(4)C(9)C(8)
O(6)C(10)C(8)
O(5)C(11)C(8)
C(11)O(5)H(1)
C(10)O(6)H(2)
C(12)O(7)H(3)
Mo(1)O(7)H(3)
106.27(8)
99.38(7)
97.41(6)
105.65(6)
98.04(6)
97.35(6)
octahedral Mo(VI) dioxo complexes with
ligands ( = 2–4) [21]). In particular, the Mo–N
bonds in structures IV , and XI are shorter than simꢀ
nꢀdentate
n
,
V
97.35(7)
97.91(6)
100.05(7)
151.31(6)
93.57(7)
159.69(7)
74.57(6)
81.31(6)
168.67(7)
85.02(7)
79.76(6)
101.78(5)
150.69(5)
89.76(6)
163.60(6)
74.50(5)
81.15(5)
170.27(5)
84.03(6)
81.41(5)
ilar bonds in the structures of the salicylaliminate
complexes [MoO2{R–N=CH–C6H4–O}2], R = Ph
(
XII) [23] and Ме (XIII) [25]: Mo–Ntrans 2.382 and
2.341 Å, respectively. The presence of the third donor
center (the oxygen atom of the ethanolamine substituꢀ
ent at the nitrogen atom) enhances the dentate charꢀ
acter of oxyazomethine ligand L on going from XII
and XIII to III
from the periphery of the bidentate ligand to the cenꢀ
tral position of the bicyclic system in structures III, V,
, V, and XI. The nitrogen atom migrates
79.29(6)
75.27(6)
78.76(5)
80.71(5)
118.49(16)
127.74(14)
113.53(11)
123.42(19)
119.03(17)
117.50(18)
138.07(13)
118.78(11)
127.48(14)
120.95(18)
122.93(18)
116.87(18)
120.20(18)
125.72(18)
106.02(15)
109.53(15)
111.87(15)
111.11(16)
108.61(16)
112.40(16)
105(2)
119.74(14)
126.68(12)
113.32(10)
133.21(11)
117.11(10)
133.28(12)
116.45(14)
119.69(16)
123.07(16)
119.09(15)
124.66(16)
119.99(16)
120.43(16)
104.42(13)
106.38(14)
110.25(14)
110.02(14)
110.00(15)
110(2)
and XI, which results in some fixation and
mobility restriction of the Mo–N bond. Note that the
Мо⎯Ntrans distances in structures III, V, and XI are
elongated by 0.160, 0.179, and 0.157 Å, respectively,
compared to the standard (“expected”) value of the
Мо–NR3 bond (2.12 Å [26]).
The Мо–О(7)(СН3ОН) bonds, which are trans
ꢀ
coordinated to О(1 oxo (2.302 and 2.305 Å in IV and V,
)
respectively) as Мо–О(СН3ОН) 2.336 Å in XI, are
elongated due to the random transꢀeffect of the multiꢀ
ply bonded oxo ligand. The lengths of these bonds in
three above mentioned structures are elongated by
0.350, 0.345, and 0.380 Å, on the average, in IV, V,
and ХI, respectively, compared to the Мо–О(3,4)cis
distances (1.952, 1.960, and 1.956 Å). The Мо–Оcis
bonds in structures IV
length with analogous values in complexes XII and
XIII containing two bidentate ( , N) ligands (Schiff
bases) (Мо–Оcis 1.942 and 1.964 Å, respectively). The
, V, and XI are comparable in
103.3(18)
114(2)
109(2)
120
О
109(3)
116(2)
117(2)
Мо–О(СН3ОН)trans bonds in structures IV
,
V, and XI
120
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
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INNER COMPLEX COMPOUNDS OF DIOXOMOLYBDENUM(VI)
Table 4. Geometric parameters of hydrogen bonds for compounds IV and
559
V*
Distance
, Å
Contact D–H⋅⋅⋅
A
Angle DHA, deg
D–H
H⋅⋅⋅A
D⋅⋅⋅A
IV
O(7)–H(3)⋅⋅⋅O(6)
0.72(3)
0.68(3)
0.69(3)
2.06(3)
2.05(3)
2.23(3)
V
2.734(2)
2.721(2)
2.879(2)
156(3)
171(3)
156(3)
O(5)–H(1)⋅⋅⋅O(4)#1
O(6)–H(2)⋅⋅⋅O(5)#2
O(5)–H(1)⋅⋅⋅O(8)#3
O(6)–H(2)⋅⋅⋅O(5)
O(7)–H(3)⋅⋅⋅O(4)#4
0.80(3)
0.77(3)
0.70(3)
2.09(3)
2.05(3)
1.94(3)
2.863(2)
2.703(2)
162(3)
143(2)
2.6323(19)
169(3)
#1
#2
#3
#4
* Symmetry transforms of equivalent atoms:
x, –y
+ 3/2,
z
+ 1/2;
–x
,
–y + 1, –
z
+ 1;
x + 1/2, –y + 1/2, z + 1/2; –1, y, z.
14. Zhang Cungen, Zu Peizi, Wu Dan, and Ju Kaibei,
are 0.212, 0.215, and 0.246 Å longer than the standard
Мо–ОR2 bond (2.09 Å [26]).
J. Chem. Res., 2000, no. 8, p. 402.
15. Odabasoglu, M., Albayrak, C., Buyukgungor O., et al.,
Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2003,
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Translated by E. Yablonskaya
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RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
No. 8
2013