Design, synthesis, and spectral parameters of transition metal coordination compounds based on organic autocomplexes

Article abstract of DOI:10.1134/S1070428011100113

Organic autocomplexes prepared from 3,5-dinitrobenzoyl chloride and some heterocyclic amines were used to synthesize a series of new coordination compounds with 3d transition metals. The new metal complexes displayed in the electronic absorption spectra charge-transfer bands typical of the initial ligands and an additional long-wave maximum in the region λ 500-625 nm. Pleiades Publishing, Ltd., 2011.

Full text of DOI:10.1134/S1070428011100113

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 10, pp. 1515–1520. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © I.G. Il’ina, O.V. Mikhalev, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 10, pp. 1488–1493.
Design, Synthesis, and Spectral Parameters of Transition Metal
Coordination Compounds Based on Organic Autocomplexes
I. G. Il’ina and O. V. Mikhalev
Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992 Russia
e-mail: igi@org.chem.msu.ru
Received July 12, 2010
Abstract—Organic autocomplexes prepared from 3,5-dinitrobenzoyl chloride and some heterocyclic amines
were used to synthesize a series of new coordination compounds with 3d transition metals. The new metal
complexes displayed in the electronic absorption spectra charge-transfer bands typical of the initial ligands and
an additional long-wave maximum in the region λ 500–625 nm.
DOI: 10.1134/S1070428011100113
In recent years, interest in studies in the field of
supramolecular chemistry has increased due to the ne-
cessity of new chemical structures as building blocks
capable of self-organization to form stable supramolec-
ular assemblies. Problems of supramolecular chemistry
were originally formulated by its founder J.-M. Lehn
[1] as studies on structured stable non-covalently
bound aggregates. As experimental data accumulated
with time, the scope of supramolecular chemistry was
considerably extended, and it now comprises studies
on all types of interactions, from weak intermolecular
to strong coordination [2, 3]. Design of molecular en-
sembles as supramolecular systems of new generation
is based on a predetermined combination of intra- and
intermolecular interactions, and the most important
factors responsible for the possibility for the formation
of self-organized supramolecular systems turned out to
be the presence in the initial ligand molecule of three
types of reactive centers, namely those ensuring hydro-
gen bonding, stacking interaction, and coordination
with metal ions [4, 5].
control over the activity of reaction centers therein.
Therefore, it may be expected that organic compounds
characterized by intramolecular donor–acceptor (D–A)
interactions (so-called autocomplexes) could be appro-
priate ligands for building up supramolecular metal
complex systems, in which intramolecular charge
transfer is possible in addition to the three types of
interactions listed above. Thus development of new
methods of synthesis, diagnostics, and investigation of
donor–acceptor metal complexes and studies on their
electronic structure could considerably supplement
known information on factors determining the possi-
bility for formation of self-organized supramolecular
systems and general relations holding therein.
In the present work we propose possible approaches
to solution of the above problem on the basis of molec-
ular design, synthesis, and analysis of new donor–
acceptor complexes of 3d transition metals as potential
building blocks for construction of self-organized
supramolecular systems. In the first step of our study
we synthesized autocomplexes Ia and Ib consisting of
a dinitrobenzamide acceptor fragment and a nitrogen-
containing heterocycle as donor fragment.
On the other hand, the significance of systems
based on donor–acceptor chromophores with strong
electron conjugation between donor and acceptor frag-
ments (intramolecular charge transfer, ICT) should not
be excluded from consideration [6]. However, the key
problem related to the role of electronic structure
determined by ICT was not studied in detail, though
control over ICT makes it possible to purposefully
vary the degree of charge transfer and hence electron
density distribution in molecule. In other words, varia-
tion of electronic parameters of a molecule ensures
O
O2N
X
N
H
NO2
Ia, Ib
X = pyridin-4-yl (a), quinolin-5-yl (b).
1515

IL’INA, MIKHALEV
Scheme 1.
1516
H2O
O2NO
ONO2
M
O
N
N
O
H2O
O2N
NO2
M(NO3)2 ·6H2O
N
H
N
H
Ia
NO2
NO2
IIa, IIIa
H2O
O2NO
ONO2
M
N
O
N
H2O
O
M(NO3)2 ·6H2O
NO2
N
Ib
H
O2N
N
H
NO2
NO2
IIb
II, M = Co; III, M = Ni.
While performing systematic studies on the series
of autocomplexes with the general formula A–Z–D
[where A and D are acceptor and donor fragments,
respectively, and Z is a bridging moiety (or spacer)],
we previously synthesized a series of analogous amide
derivatives with various donor fragments and studied
in detail charge transfer in their molecules [7]. The
results of spectral studies showed that these com-
pounds should be regarded as autocomplexes with NH
bridging moiety rather than structures with two-mem-
bered CO–NH spacer (as presumed initially).
m = 0, M = Ni; VII, n = 4, m = 0, M = Ni; L = Ib, n =
m = 1: VIII, L″ = Me2CO, M = Co; IX, L″ = Me2CO,
M = Ni; X, L″ = MeCN, M = Ni.
Unlike pyridine-containing ligand Ia from which
the corresponding cobalt and nickel complexes IIa and
IIIa can be obtained in alcohol, quinoline-containing
ligand Ib with alcohol formed associate IV, and com-
plex formation did not occur. Cobalt complex IIb can
be obtained using a different solvent, e.g., acetonitrile.
Nickel complexes were isolated as adducts with
acetone or acetonitrile.
We previously showed [8, 9] that autocomplexes
can be used as bidentate ligands to obtain metal
chelates. However, coordination compounds of metals
with autocomplexes as ligands were not reported so
far. We tried to use autocomplexes Ia and Ib as ligands
(L) to synthesize cobalt(II) and nickel(II) complexes
with the composition ML2(NO3)2(H2O)2. Ligands Ia
and Ib were prepared by heating equimolar amounts of
3,5-dinitrobenzoyl chloride and 4-aminopyridine or
5-aminoquinoline in acetone in the presence of
an equimolar amount of triethylamine. Reactions of
ligands Ia and Ib with cobalt(II) or nickel(II) nitrate
hexahydrate in appropriate solvent gave metal com-
plexes IIa, IIb, and IIIa (Scheme 1).
The obtained compounds were high-melting yel-
lowish (ligands Ia and Ib) and light red or greenish–
blue (metal complexes) finely crystalline substances.
The complexes changed their color on heating to 100–
180°C due to loss of solvate and/or hydrate shell. The
structure of the products was confirmed by elemental
analysis and IR and UV spectroscopy. The IR spectra
(KBr) contained absorption bands in the regions 1550–
1500 and 1350–1330 cm–1 due to antisymmetric and
symmetric vibrations of nitro groups in the aromatic
ring, stretching vibration band of the amide carbonyl
group was observed at 1670–1710 cm–1, and stretching
vibrations of aromatic C–H bonds gave rise to absorp-
tion at 3095 cm–1. Absorption bands due to stretching
vibrations of the NH group in the initial ligands (3180–
3150 cm–1) were displaced to higher frequencies
(3400–3300 cm–1) upon complex formation.
Depending on the conditions (temperature, reaction
time, solvent nature) complexes L2(NO3)2M·nH2O·
mL″ (V–X) with different compositions may be ob-
tained, including adducts VIII–X containing solvent
molecule L″: L = Ia: V, n = m = 0, M = Co; VI, n =
The most valuable information on intramolecular
charge transfer was obtained by analysis of the elec-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011

DESIGN, SYNTHESIS, AND SPECTRAL PARAMETERS OF TRANSITION METAL
1517
Electronic absorption spectra of autocomplexes Ia and Ib and metal complexes IIa, IIb, IIIa, and X in acetonitrile
(c = 5×10–4 M) and ionization energies of donor fragments
λmax, nm (ε, l mol–1 cm–1)
Comp. no.
Ei., eV
CTKdinitro
CT
ICT-I (autocomplex) ICT-II (metal complex)
CO
NHX
Ia
9.26 [13]
233 (27900)0
228 (66280)0
231 (48340)0
229 (39270)0
226 (111830)
227 (100000)
260 (14412)
265 (46790)
262 (34640)
294 (8005)0
293 (17178)
293 (15355)
–
–
IIa
IIIa
Ib
–
518 (94)
610 (18)
–
–
8.67 [14]
314 (6712)0
316 (14216)
314 (12800)
IIb
Xa
514 (65)
625 (22)
a
Nickel complex X is an adduct with acetonitrile.
tronic absorption spectra of coordination compounds
IIa, IIb, IIIa, and X in comparison with the spectra of
initial ligands Ia and Ib. The electronic absorption
spectra of these compounds contained four maxima
with different intensities in the λ range from 230 to
625 nm (see table). The bands were assigned by em-
pirical procedure [10] based on decomposition of
a molecule into polar chromophores. This procedure
was developed for polysubstituted benzenes of donor–
acceptor type, and it makes it possible to determine the
number of absorption bands and their origin without
resorting to quantum-chemical calculations. The proce-
dure was validated by us previously [7–9, 11, 12] using
a large number of both autocomplexes and metal
chelates based thereon.
Like initial autocomplexes Ia and Ib, the electronic
absorption spectra of their coordination compounds
with metals contained charge transfer bands belonging
mainly to electron transitions in the ligand. According
to the empirical procedure described in [10] and the
data of [7], these bands should be assigned as follows
(see table). The short-wave band at λ 230 nm corre-
sponds to charge transfer from the aromatic ring to
nitro group (nitrobenzene band CTdKinitro) which is the
vector sum of transitions from the ring to each meta-
nitro group (CTKnitro). The blue shift of that band
relative to the corresponding band of nitrobenzene
(λmax 250 nm, ε 8900 [17]) may be rationalized in
terms of reduced donor power of the aromatic ring due
to opposite transition from the ring to the acceptor
carbonyl group (CTKCO). Next follows (in order of de-
creasing excitation energy) a band which, according
to [16], results from intramolecular interaction of
chromophores B and C, involving electron density
transfer from the donor fragment to acceptor along the
conjugation chain. This band originates from charge
The compounds under study were arbitrarily
represented as a model system which, in keeping with
the quasi-autonomous model [15], was divided into
donor–acceptor type components; theoretically pos-
sible charge transfer bands and direction of their
polarization were determined, and the bands of the
components were summed.
transfer from the substituted amino group (donor frag-
CO
NHX
ment NH–X) to the acceptor carbonyl group (CT
)
1
According to the data of [16], the electronic spectra
of counter-polarized quasi-autonomous donor–accep-
tor systems like B–C contain an additional broad band
which is absent in the total absorption of the com-
ponents that are simpler compounds including only
acceptor or donor fragment. This band originates from
intramolecular interaction of chromophore systems B
and C as a result of electron transfer from the donor
fragment to acceptor along the conjugation chain. As
applied to ligands Ia and Ib, the corresponding band
with a contribution of LB electron transition in the
aromatic chromophore. The maximum at a longer
wavelength (λ ~300 nm) reflects intramolecular charge
transfer (ICT-I) in a conformation ensuring spatial prox-
imity of the donor and acceptor components, and the
transition occurs in the contact mode through space.
O
O2N
X
N
H
arises from charge transfer from the donor amino
CO
group (NH–X) to acceptor carbonyl group (CT
)
C
NHX
NO2
1
with a contribution of LB type transition in the aro-
matic chromophore.
B
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011

IL’INA, MIKHALEV
1518
Apart from the above ligand bands, the metal com-
1H NMR spectra were recorded from solutions in
CD3OD on a Bruker Avance DPX 400 spectrometer
(400 MHz) using TMS as internal reference.
plexes displayed in the electronic absorption spectra
an additional low-intense long-wave maximum (ICT-
II) in the region λ 500–625 nm, which characterizes
bond configuration at the central metal ion.
Commercially available pyridin-4-amine, quinolin-
5-amine, 3,5-dinitrobenzoic acid, and cobalt(II) and
nickel(II) nitrate hexahydrates were used without addi-
tional purification. 3,5-Dinitrobenzoyl chloride was
synthesized by heating 3,5-dinitrobenzoic acid in
boiling thionyl chloride containing 2–3 drops of di-
methylformamide; the crude product was crystallized
from a minimal amount of hot toluene and dried [18].
Thus the presence of a long-wave absorption band
(ICT-II) which is absent in the electronic absorption
spectra of the initial ligands and increased (by a factor
of 1.5–2) intensity of the other absorption bands due to
doubling of interacting fragments may be regarded as
evidences in support of complex formation.
Comparison of the electronic absorption spectra of
Autocomplexes Ia and Ib (general procedure).
A solution of 5 mmol of 3,5-dinitrobenzoyl chloride,
5 mmol of pyridin-4-amine or quinolin-5-amine, and
5 mmol of triethylamine in 30 ml of acetone contain-
ing 5 ml of ethanol (to avoid crystallization of triethyl-
amine hydrochloride) was heated for 40 min under
reflux. The mixture was cooled and left overnight in
a refrigerator. The precipitate was filtered through
a glass filter and washed with cold alcohol, the filtrate
was evaporated, and the residue was combined with
the main portion of the product, recrystallized from
aqueous acetone, and dried in air.
ligands Ia and Ib and metal complexes based thereon
CO
NHX
(see table) shows that the intensity of the CT
band
of the complexes with ligand Ia is considerably higher
than the intensity of the corresponding band of the
complexes with ligand Ib. On the other hand, unlike
ligand Ib, the intensity of the ICT-I band in the spectra
of ligand Ia and its complexes is reduced so strongly
that it becomes almost indistinguishable at λ ~ 300 nm.
It may be presumed that the conformation of pyridine-
containing derivatives excludes ICT through space.
As a result, intramolecular interaction of chromophore
systems B and C in compound Ia and its complexes
involves mainly charge transfer along the conjugation
chain, and the intensity of the corresponding band con-
siderably increases. Although autocomplex Ib contains
a stronger donor fragment, some blue shift of the nitro-
benzene band in its electronic absorption spectrum
may be attributed to a large contribution of electron
density transfer from the donor fragment in the
contact mode.
3,5-Dinitro-N-(pyridin-4-yl)benzamide (Ia).
Yield 75%, light brown crystals, mp 240–250°C
1
(decomp.). H NMR spectrum, δ, ppm: 7.91 d (2H,
pyridine), 8.52 d (2H, pyridine), 9.25 s (1H, Harom),
9.33 s (2H, Harom). Mass spectrum: m/z (Irel, %): 289
(100) [M + H]+, 288 (46) [M]–. Found, %: C 50.21;
H 2.69; N 19.28. C12H18N4O5. Calculated, %: C 50.01;
H 2.80; N 19.44. M 288.22
3,5-Dinitro-N-(quinolin-5-yl)benzamide (Ib).
Yield 85%, light brown needles (from acetone or
acetonitrile), mp 245°C. H NMR spectrum, δ, ppm:
EXPERIMENTAL
1
7.63 d.d (1H), 7.86 d.t (2H), 8.08 d (1H), 8.58 d (1H),
and 8.94 d (1H) (quinoline); 9.25 s (1H) and 9.33 s
(2H) (C6H2). Mass spectrum: m/z (Irel, % ): 339 (100)
[M + H]+, 338 (20) [M]–. Found, %: C 56.72; H 2.82;
N 16.45. C16H10N4O5. Calculated, %: C 56.81; H 2.98;
N 16.56. M 338.28.
The electronic absorption spectra were measured on
a Thermo Evolution-300 BB spectrophotometer from
solutions in acetonitrile with a concentration of 5×
10–4 M (cell path length 0.1 or 1 cm). The IR spectra
were recorded on a Thermo-Nicolet IR 200 spectrom-
eter with Fourier transform; in some cases, attenuated
total reflectance spectra were recorded to avoid un-
desirable absorption in the region of 3400 cm–1 (OH
stretching vibrations). The progress of reactions and
the purity of products were monitored by TLC on
Silufol UV-254 plates using toluene–acetone (1:1) as
eluent. The mass spectra (MALDI, positive and nega-
tive ion detection) were obtained on a Bruker Auto-
flex II instrument (FWHM resolution 18000); samples
were applied onto a polished steel support. The
Metal complexes (general procedure). The corre-
sponding transition metal salt, 1 mol, was added to
a hot solution of 2 mol of compound Ia or Ib in alco-
hol, acetone, or acetonitrile, and the resulting homo-
geneous solution was heated for 5 h under reflux,
cooled, and left to stand on exposure to air for slow
evaporation. The precipitate was filtered off, washed
with several portions of the corresponding cold sol-
vent, and dried in air.
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DESIGN, SYNTHESIS, AND SPECTRAL PARAMETERS OF TRANSITION METAL
1519
Bis[3,5-dinitro-N-(pyridin-4-yl)benzamide]-
cobalt(II) dinitrate dihydrate (IIa). Yield 80%, light
red crystals, mp >160°C (decomp.). Found, %: C 36.43;
H 2.84; N 17.45. C24H20CoN10O18. Calculated, %:
C 36.24; H 2.53; N 17.61.
light–red crystalline powder, mp >160°C (decomp.).
Found, %: C 45.12; H 2.75; N 15.39. C35H28CoN10O18.
Calculated, %: C 44.93; H 3.02; N 14.97.
Bis[3,5-dinitro-N-(quinolin-5-yl)benzamide]-
nickel(II)–nitrate–acetone–water (1/1/1/1) (IX) was
obtained using acetone as solvent. Yield 87%, greenish
finely crystalline powder, mp >300°C (decomp.).
Found, %: C 45.24; H 2.31; N 15.86. C35H28N10NiO18.
Calculated, %: C 44.94; H 3.02; N 14.98.
Bis[3,5-dinitro-N-(quinolin-5-yl)benzamide]-
cobalt(II) dinitrate dihydrate (IIb) was synthesized
using acetonitrile as solvent. Yield 89%, light red crys-
talline powder, mp >225°C (decomp.). Found, %:
C 43.20; H 2.48; N 15.59. C32H24CoN10O18. Calculat-
ed, %: C 42.92; H 2.70; N 15.64.
Bis[3,5-dinitro-N-(quinolin-5-yl)benzamide]-
nickel(II)–nitrate–acetonitrile–water (1/1/1/1) (X)
was obtained using acetonitrile as solvent. Yield 90%,
large greenish–blue crystals, mp >225°C (decomp.).
Found, %: C 44.27; H 2.55; N 16.35. C34H25N11NiO17.
Calculated, %: C 44.47; H 2.74; N 16.78.
Bis[3,5-dinitro-N-(quinolin-5-yl)benzamide]-
nickel(II) dinitrate dihydrate (IIIa) was synthesized
by prolonged (10–20 days) keeping of a solution of an-
hydrous complex VI in alcohol at room temperature.
Yield quantitative, grayish–green crystals, mp >170°C
(decomp.). Found, %: C 36.29; H 2.60; N 17.59.
C24H20N10NiO18. Calculated, %: C 36.24; H 2.54;
N 17.62.
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3,5-Dinitro-N-(quinolin-5-yl)benzamide–ethanol
(1/1) (IV) was isolated by recrystallization of auto-
complex Ib from ethanol. Yield quantitative, light
yellow plates, mp 245°C. Found, %: C 56.62; H 4.25;
N 14.61. C18H16N4O6. Calculated, %: C 56.25; H 4.20;
N 14.58.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 10 2011

IL’INA, MIKHALEV
1520
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