Coordinating ability of rhodium(III) porphyrins toward organic bases

Article abstract of DOI:10.1134/S107036321512021X

Reactions of hydroxo(2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) and acetylacetato-(5,10,15,20-tetraphenylporphyrinato)rhodium(III) with nitrogen-containing substrates were studied by spectrophotometry. The stability constants and compositions of the resulting molecular complexes were determined, and the effects of the macrocycle nature and substrate basicity on the stability constants were estimated. The structures of the isolated rhodium porphyrin molecules and their complexes with organic bases were optimized by the PM3 quantum chemical method. The degree of macrocycle deformation was found to change in the course of metal-substrate coordination. A correlation between the metal-substrate bond energy and equilibrium constant was revealed.

Full text of DOI:10.1134/S107036321512021X

ISSN 1070-3632, Russian Journal of General Chemistry, 2015, Vol. 85, No. 12, pp. 2786–2792. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © S.V. Zaitseva, S.A. Zdanovich, T.I. Bryukhanova, O.I. Koifman, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 12,
pp. 2057–2063.
Coordinating Ability of Rhodium(III) Porphyrins
toward Organic Bases
a
a
b
a,b
S. V. Zaitseva , S. A. Zdanovich , T. I. Bryukhanova , and O. I. Koifman
a
Krestov Institute of Solution Chemistry, Russian Academy of Sciences,
ul. Akademicheskaya 1, Ivanovo, 153045 Russia
e-mail: svz@isc-ras.ru
b
Ivanovo State University of Chemistry and Technology, Sheremetevskii pr. 7, Ivanovo, 153000 Russia
Received May 8, 2015
Abstract—Reactions of hydroxo(2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) and acetylacetato-
5,10,15,20-tetraphenylporphyrinato)rhodium(III) with nitrogen-containing substrates were studied by spectro-
(
photometry. The stability constants and compositions of the resulting molecular complexes were determined,
and the effects of the macrocycle nature and substrate basicity on the stability constants were estimated. The
structures of the isolated rhodium porphyrin molecules and their complexes with organic bases were optimized
by the PM3 quantum chemical method. The degree of macrocycle deformation was found to change in the
course of metal–substrate coordination. A correlation between the metal–substrate bond energy and equilibrium
constant was revealed.
Keywords: porphyrin, rhodium, complex, coordination, organic base
DOI: 10.1134/S107036321512021X
Platinum group metals are characterized by a wide
range of possible oxidation states which can occur in
their coordination compounds. Macrocyclic tetra-
pyrrole complexes of platinum metals combine unique
structural specificity of the ligand with valuable physico-
chemical properties of the metal and can therefore be
successfully used for the synthesis of biologically
active compounds, as well as catalysts in various
processes and analytical receptors [1–7]. In particular,
rhodium porphyrins attract interest due to their ability
to activate hydrogen transfer reactions [8–11] and act
as active redox or photophysical agents [12–15]. They
are also used in the preparation of biomimetic models
of vitamin B [16] and cytochrome c [12].
[(OH)RhOEP] and acetylacetato(5,10,15,20-tetra-
phenylporphyrinato)rhodium(III) [(acac)RhTPP] with
nitrogen-containing bases (L), imidazole, 1-methyl-
imidazole, 2-methylimidazole, pyridine, and diethylamine.
The reaction of rhodium porphyrins with nitrogen
bases [Eq. (1)] was accompanied by red shift and
change of the intensity of the main absorption bands in
the electronic spectra (Fig. 1). The spectral curves
recorded at dif-ferent substrate concentrations showed
distinct iso-sbestic points. This pattern indicated
equilibrium coordination of the organic substrate to
rhodium [17–20]. The shift (Δλ) of the B band (λmax
=
4
18 nm) in the spectrum of rhodium tetraphenyl-
1
2
porphyrin was 7–8 nm. The B band of rhodium
octaethylporphyrin (λmax = 405 nm) was displaced by
Further search and design of rhodium porphyrin-
based systems that could show the highest activity in
practically important processes implies study of the
coordination ability of these compounds with respect
to various substrates and features of donor–acceptor
interaction. As a part of our studies on the coordination
properties of platinum metal porphyrins, in the present
work we examined the complexation of hydroxo-
10–12 nm. The Δλ value almost did not depend on the
substrate basicity.
In the titration of a benzene solution of rhodium
porphyrin with a solution of organic base equilibrium
in the system established instantaneously throughout
the examined substrate concentration range. The
titration curve was smoothly ascending or descending,
depending on the wavelength (Fig. 1), which is typical
(2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III)
2
786

COORDINATING ABILITY OF RHODIUM(III) PORPHYRINS
2787
OH
Rh
Acac
Rh
N
N
N
N
N
N
N
N
(OH)RhOEP
(acac)RhTPP
X)RhP + nL ⇄ (X)Rh(L) Р.
K
eq
(
n
(1)
of one-step process. The composition of the complex
was determined by the Bent–French method [21], H
NMR, and mass spectrometry.
appeared in a much stronger field (δ = 1.97 ppm). High
basicity of the other substrates and analogous character
of variation of the electronic absorption spectra, as
well as spectrometric data, allowed us to presume 1 : 1
composition of the corresponding complexes.
1
From the slope of the linear plot of log [(A – A )/
eq
0
(
A – A )] versus log c (Fig. 2) we determined the
∞ eq L
number of coordinated substrate molecules (n = 1).
The mass spectra of the rhodium porphyrin complexes
with imidazole contained the molecular ion peaks with
m/z 720.56 and 882.76 corresponding to (OH)Rh(Im)·
OEP and (acac)Rh(Im)TPP, respectively.
Donor–acceptor interaction is a reversible process
characterized by an equilibrium constant (K ). Analysis
eq
of the obtained data (see table) showed that the
stability of rhodium porphyrin complexes increases in
the series Py < 2-MeIm < Im < 1-MeIm. The stability
The formation of these complexes was also
constant K is linearly related to the substrate basicity
eq
1
1
confirmed by the H NMR data. In the H NMR
spectrum of (acac)Rh(Im)TPP, signals from the pyrrole
protons in the macrocycle appeared in a stronger field
relative to the corresponding signal of (acac)RhTPP
(pK ). However, diethylamine (pK = 10.68) does not
a
a
(
a)
A
(
δ = 8.86 and 8.97 ppm, respectively). This signal shift
(b)
A
may be caused by change of the position of the central
metal ion with respect to the coordination plane as a
result of addition of imidazole to the trans position
with respect to the anionic ligand. Signals from
protons of the acetylacetonate ligand in the spectrum
of (acac)Rh(Im)TPP were displaced downfield relative
to those of (acac)RhTPP (δ = 7.13 and 2.63 ppm
against δ = 5.32 and 2.12 ppm), which may be due to
elongation of the Rh–Cacac bond and increase of the
distance between the ligand protons and the
macrocycle. On the other hand, a strong upfield shift
of the NH signal of imidazole was observed relative to
the corresponding signal of the free base (from δ =
4
с × 10 , mol/L
Im
8
.47 to 1.58 ppm). Obviously, this is the result of
shielding effect of the porphyrin macrocycle on pro-
tons of imidazole coordinated to the metal. No
appreciable variation of signals from protons in the
λ, nm
Fig. 1. (a) Electronic absorption spectra of (OH)RhOEP
–6
1
[c(OH)RhOEP = 8.22×10 M] in the presence of imidazole
–5 –3
macrocycle was observed in the H NMR spectrum of
(
c
Im = 1.01×10 → 2.86×10 M) in benzene and (b) the
(
OH)Rh(Im)OEP, but the imidazole NH signal
corresponding spectrophotometric titration curve at λ = 405 nm.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 12 2015

2
788
ZAITSEVA et al.
0 ∞
log (Aeq – A )/(A – Aeq)
0 ∞
log (Aeq – A )/(A – Aeq)
8
9
6
7
1
0
–
log c
L
–
log c
L
Fig. 2. Plots of log (Aeq – A
0
)/(A
∞
– Aeq) vs –logc
L
: (1) (OH)Rh(Py)OEP (tanα = 1.06), (2) – (OH)Rh(Im)OEP (tanα = 1.02),
(
(
(
3) (OH)Rh(1-MeIm)OEP (tanα = 1.03), (4) (OH)Rh(2-MeIm)OEP (tanα = 0.98), (5) (OH)Rh(Et NH)OEP (tanα = 1.11),
2
6) (acac)Rh(Im)TPP (tanα = 1.03), (7) (acac)Rh(2-MeIm)TPP (tanα = 0.95), (8) (acac)Rh· (Et
9) (acac)Rh(Py)TPP (tanα = 1.04), (10) (acac)Rh(1-MeIm)TPP (tanα = 1.01).
2
NH)TPP (tanα = 0.98),
fit this relation. Presumably, its coordination is
hindered for steric reasons, so that the corresponding
complex is less stable than might be expected from the
porphyrin ligand, which favors increase of the
effective positive charge on the metal ion and hence
formation of a stronger metal–substrate coordination
bond.
pK value.
a
It should be noted that the complexes formed by
organic bases with (acac)RhTPP are more stable than
those obtained from (OH)RhOEP (see table). The
reason is electron-withdrawing effect of four phenyl
substituents in (acac)RhTPP on the basicity of the
The examined rhodium porphyrin complexes turned
out to be more stable than analogous complexes
derived from osmium and ruthenium porphyrins [22].
This may be rationalized by the different natures of
metal ions and their coordination environment. Coor-
Stability constants of donor–acceptor complexes of rhodium porphyrins, substrate basicities, and metal–ligand bond lengths
and energies
2
98
Complex
K
eq , L/mol
рK
а
d
Rh–L, Å
2.21
–ERh–L, kcal/mol
47.23
(
(
(
(
(
(
(
(
(
(
2
OH)Rh(Et NH)OEP
26900±3520
41800±2600
17500±1430
4090±402
10.67
7.33
6.65
5.89
5.29
10.67
7.33
6.65
5.89
5.29
OH)Rh(1-MeIm)OEP
2.042
2.053
2.064
2.070
2.181
2.013
2.031
2.047
2.053
58.72
OH)Rh(Im)OEP
53.42
OH)Rh(2-MeIm)OEP
OH)Rh(Py)OEP
51.86
706±42.1
44.83
2
acac)Rh(Et NH)TPP
52500±6370
191000±21700
47300±4650
10900±1960
1193±223
56.28
acac)Rh(1-MeIm)TPP
acac)Rh(Im)TPP
65.72
62.65
acac)Rh(2-MeIm)TPP
acac)Rh(Py)TPP
60.10
54.11
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 12 2015

COORDINATING ABILITY OF RHODIUM(III) PORPHYRINS
2789
(
OH)RhOEP
(acac)RhTPP
(OH)Rh(1-MeIm)OEP
(acac)Rh(1-MeIm)TPP
Fig. 3. Structures of the isolated molecules of rhodium porphyrins and their complexes with 1-methylimidazole according to PM3
quantum chemical calculations.
dination of an organic substrate to osmium and ruthe-
nium porphyrins involves replacement of coordinated
water molecules in the initial complex [22], whereas
rhodium porphyrins take up an organic base at the
vacant sixth coordination site. Direct addition of a
nitrogen base requires much less energy than
substitution, and the metal–substrate bond thus formed
is stronger. Furthermore, trans and cis effects of the
ligands provide an appreciable contribution to the
stability of the complexes.
stronger complexes with organic bases. However, our
experimental data showed the opposite (see table).
Obviously, the stability of the complexes under study
is determined mainly by electronic effects of the
substituents in the macrocycle rather than by
conformational factors.
It was found that substrate coordination at the trans
position with respect to the anionic is more
energetically favorable (see table, Fig. 3). Such
coordination changes the character of steric strain in
the macrocycle (Figs. 3, 4). Depending on the organic
base, the average deviation of the skeletal atoms from
the mean molecular plane increases by 0.013–0.04 Å
for (OH)RhOEP and decreases by 0.014–0.38 Å for
The complexation of organic bases with rhodium
porphyrins was also studied by computer simulation
[23–25]. Our quantum chemical calculations showed
that rhodium porphyrin molecules have nonplanar
structure with C symmetry (Fig. 3). Rhodium tetra-
4
v
(
acac)RhTPP. The complexes derived from rhodium
phenylporphyrin and rhodium octaethylporphyrin are
characterized by preferentially saddle type distortion
tetraphenylporphyrin generally retain the deformation
type typical of the initial complex, whereas bowl-type
deformation becomes predominant for the complexes
of (OH)RhOEP.
(
Fig. 4). The average deviation of the skeletal atoms of
the macrocycle along the z axis from the xy mean plane
is 0.074 and 0.011 Å for (acac)RhTPP and
(
(
(
OH)RhOEP, respectively, i.e., the macrocycle in
acac)RhTPP is distorted to a greater extent than in
OH)RhOEP. Increase of steric strain in the porphyrin
It should be noted that the formation of metal–
substrate donor–acceptor bond induces different deforma-
tions of the macrocycle. In going from (acac)RhTPP to
(acac)Rh(L)TPP, reduction of the torsional strain and
increase of the plane strain in the pyrrole fragments are
observed, whereas (OH)Rh(L)OEP features the op-
ligand is accompanied by reduction of its aromaticity
and increase of the basicity. Therefore, it could be
expected that rhodium octaethylporphyrin would form
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 12 2015

2
790
ZAITSEVA et al.
(acac)RhTPP
(acac)Rh(1-MeIm)TPP
(acac)Rh(2-MeIm)TPP
ΔZ, Å
ΔZ, Å
ΔZ, Å
Atom no.
acac)Rh(Im)TPP
Atom no.
Atom no.
(acac)Rh(Et NH)TPP
(
(acac)Rh(Py)TPP
2
ΔZ, Å
ΔZ, Å
ΔZ, Å
Atom no.
Atom no.
Atom no.
(OH)RhOEP
(OH)Rh(1-MeIm)OEP
(OH)Rh(2-MeIm)OEP
ΔZ, Å
ΔZ, Å
ΔZ, Å
Atom no.
Atom no.
Atom no.
(OH)Rh(Im)OEP
(OH)Rh(Py)OEP
2
(OH)Rh(Et NH)OEP
ΔZ, Å
ΔZ, Å
ΔZ, Å
0
.1
0.1
0
.0
0.0
–
0.1
–0.1
Atom no.
Atom no.
Atom no.
Fig. 4. Deviations of skeletal atoms of the porphyrin macrocycle along the z axis from the average plane for rhodium porphyrins and
their complexes according to PM3 quantum chemical calculations.
posite pattern (Fig. 4). Increase of the torsional strain
affects the Rh–L bond energy, which should reduce the
stability of the complexes. In fact, this is confirmed by
the experimental data (see table).
charge on the central metal ion, coordination environ-
ment, and substrate nature. The stability of the
resulting complexes also depends on the conforma-
tional change of the porphyrin ligand as a result of
metal–substrate coordination.
Analysis of the structure and energy parameters
revealed a relation between the energy (ERh–L) and
length (strength) of the Rh–L bond (lRh–L), on the one
hand, and substrate basicity, on the other. Comparison
of the calculated and experimental data suggests a
The results of this study may be useful for the
design of efficient catalysts and biomimetic systems.
EXPERIMENTAL
correlation between K and E
(see table).
eq
Rh–L
The electronic absorption spectra were measured in
the λ range from 380 to 700 nm in benzen on a Varian
Cary-50 spectrophotometer. The optical densities at a
We can conclude that the coordination ability of
rhodium porphyrins is determined by the effective
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 12 2015

COORDINATING ABILITY OF RHODIUM(III) PORPHYRINS
2791
constant rhodium porphyrin concentration and dif-
ferent concentrations of organic bases were measured
at λ = 404–428 nm using 1-cm cells. The H NMR
spectra were recorded on a Bruker Avance 500
spectrometer. The mass spectra (electrospray ioniza-
tion) were obtained on a Bruker microTOF mass
spectrometer.
CH , acac). Electronic absorption spectrum (benzene),
λmax, nm (logε): 574.0 (3.20), 524.0 (4.31), 418.0 (5.28).
3
1
Hydroxo(imidazole)(2,3,7,8,12,13,17,18-octa-
1
ethylporphyrinato)rhodium(III). H NMR spectrum
(
CDCl ), δ, ppm: 10.14 s (4H, meso-H), 7.72 s (1H, 2-
3
H, Im), 7.14 s (2H, 4-H, 5-H, Im), 4.08 m (16H,
CH CH , J = 14.0 Hz), 1.97 s (1H, NH, Im), 1.72 q
2
3
(
24H, CH CH , J = 6.3 Hz), 1.14 s (H, OH).
2 3
Hydroxo(2,3,7,8,12,13,17,18-octaethylporphyri-
nato)rhodium(III) [(OH)RhOEP] or acetylacetonato-
Acetylacetonato(imidazole)(5,10,15,20-tetra-
1
(
[
5,10,15,20-tetraphenylporphyrinato)-rhodium(III)
(acac)RhTPP] (general procedure) [26]. A mixture of
phenylporphyrinato)rhodium(III). H NMR spec-
trum (CDCl ), δ, ppm: 8.86 s (8H, β-pyrrole), 8.18 d
3
0
1
.51 mmol of the corresponding porphyrin and
and 8.05 d (4H each, o-H, J = 6.9 Hz), 7.78 m (12H, p-
H, m-H, J = 8.1 Hz), 7.70 s (1H, 2-H, Im), 7.13 s (2H,
.00 mmol of RhCl ·3H O [or Rh(acac) ] in 30 mL of
3
2
3
4
-H, 5-H, Im), 7.13 s (1H, CH, acac), 2.63 s and 2.03 s
benzonitrile was heated for 3 h under nitrogen. The
solvent was removed under reduced pressure, and the
residue was subjected to silica gel chromatography
(
3H each, CH , acac), 1.58 s (1H, NH, Im).
3
The Keq values were determined by spectrophoto-
(
using methylene chloride as eluent) and dried at 80°C
metric titration according to the procedure described
21, 27] using the equation for a three-component
equilibrium mixture:
under reduced pressure to remove coordinated
benzonitrile. The product was additionally purified by
recrystallization from methylene chloride–methanol.
Yield 65–76%, purple red solid.
[
n
Keq = [(L)
n
MP]/[MP][L] .
(2)
The concentrations of colored components, metal
porphyrins and their complexes with organic bases,
were determined by spectrophotometry using the
equation
1
(
OH)RhOEP. H NMR spectrum (CDCl ), δ, ppm:
3
1
0.12 s (4H, meso-H), 4.06 m (16H, CH CH ), 1.72 t
2 3
(
24H, CH CH , J = 6.2 Hz), 1.11 s (H, OH). Electronic
2 3
absorption spectrum (benzene), λmax, nm (logε): 569.0
A = εcl,
(3)
(
4.48), 532.0 (4.03), 405.0 (5.03).
where A is the optical density, ε is the molar absorption
coefficient, c is the concentration (mol/L), and l is the
cell path length.
1
(
acac)RhTPP. H NMR spectrum (CDCl ), δ, ppm:
3
8
.97 s (8H, β-pyrrole), 8.18 d and 8.10 d (4H each, o-
H, J = 6.9 Hz), 7.74 m (12H, p-H, m-H, J = 8.1 Hz),
.32 s (1H, CH, acac), 2.12 s and 2.06 s (3H each,
Then the equilibrium constant is given by the
following equation:
5
(
Aeq – A
0
)/(A
∞
0
– A )
1
K
eq = ———————— · ————–———————–––—.
(4)
0
0
(
A
∞
– Aeq)/(A
∞
– A ) c
0 L
– cMP [1 – (Aeq – A )/(A
0 ∞
0
– A )]
0
0
Here, c are c the initial concentrations of metal
The bond lengths and bond angles in the macrocycle
were initially set on the basis of averaged data for
metal porphyrins [31]. The geometric parameters of
alkyl substituents and organic bases were taken from
[32].
MP
L
porphyrin and substrate in benzene; A , A , and A are
the optical densities corresponding to metal porphyrin,
equilibrium mixture at definit substrate
0
eq
∞
a
concentration, and the resulting complex, respectively.
The relative error in the determination of K was 5–10%.
eq
ACKNOWLEDGMENTS
Quantum chemical calculations were performed by
the PM3 method [23–25] using PC version [28] of
Gamess software package [29]. The computation was
terminated when a gradient of 0.0004 kJ mol Å was
achieved. The initial data were entered, and the results
were processed using ChemCraft (version 1.3) [30].
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 12-03-00 824-a) using the equipment of the Upper
Volga Regional Center of Physicochemical Research.
–
1
–1
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ZAITSEVA et al.
17. Stulz, E., Scott, S.M., Bond, A.D., Otto, S., and
REFERENCES
Sanders, J.K.M., Inorg. Chem., 2003, vol. 42, no. 9,
1
. Saka, E.T., Çakır, D., Bıyıklıoğlu, Z., and Kantekin, H.,
Dyes Pigm., 2013, vol. 98, no. 2, p. 255. DOI: 10.1016/
j.dyepig.2013.02.021.
p. 3086. DOI: 10.1021/ic026257a.
18. Zaitseva, S.V., Zdanovich, S.A., Semeikin, A.S., and
Koifman, O.I., Russ. J. Inorg. Chem., 2005, vol. 50,
no. 11, p. 1798.
2
3
4
5
6
. Afanasiev, P., Kudrik, E.V., Albrieux, F., Briois, V.,
Koifman, O.I., and Sorokin, A.B., Chem. Commun.,
19. Bichan, N.G., Tyulyaeva, E.Yu., and Lomova, T.N.,
Macroheterocycles, 2013, vol. 6, no. 2, p. 144. DOI:
10.6060/mhc121212l.
2012, vol. 48, no. 49, p. 6088. DOI: 10.1039/C2CC31917A.
. Liu, C.-J., Yu, W.-Y., Peng, S.-M., Mak, T.C.W., and
Che, C.-M., J. Chem. Soc., Dalton Trans., 1998, vol. 48,
p. 1805. DOI: 10.1039/A800535D.
. Caselli, A., Gallo, E., Ragaini, F., Ricatto, F., Abbiati, G.,
and Cenini, S., Inorg. Chim. Acta, 2006, vol. 359, no. 9,
p. 2924. doi: 10.1016/j.ica.2005.11.020.
. Smieja, J.A., Borneman, M., Kittilstved, K., Edwards, D.,
and Borda, E., Polyhedron, 2002, vol. 21, no. 19,
p. 1889. DOI: 10.1016/S0277-5387(02)01078-1.
. Mamardashvili, N.Zh. and Koifman, O.I., Macro-
heterocycles, 2011, vol. 4, no. 1, p. 30. DOI: 10.6060/
mhc2011.1.06.
2
0. Zaitseva, S.V., Zdanovich, S.A., and Golubchikov, O.A.,
Russ. J. Coord. Chem., 2002, vol. 28, no. 12, p. 843.
DOI: 10.1023/A:1021630228084.
2
1. Bulatov, M.I. and Kalinkin, I.P., Prakticheskoe ruko-
vodstvo po fotokolorimetricheskim
i
spektrofoto-
metricheskim metodam analiza (A Practical Guide to
Photocolorimetric and Spectrophotometric Analytical
Methods), Leningrad: Khimiya, 1968.
2
2. Zaitseva, S.V., Zdanovich, S.A., and Koifman, O.I.,
Russ. J. Inorg. Chem., 2015, vol. 60, no. 6, p. 759. DOI:
1
0.1134/S0036023615060182.
7
. Koifman, O.I. and Ageeva, T.A., Ros. Khim. Zh., 2004,
vol. 48, no. 4, p. 140.
2
2
2
2
3. Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, no. 2,
p. 221. DOI: 10.1002/jcc.540100208.
8. Collman, J.P., Ha, Y., Guilard, R., and Lopez, M.A.,
4. Fletcher, R., Methods of Optimization, New York:
Inorg. Chem., 1993, vol. 32, no. 9, p. 1788. DOI:
Wiley, 1980, p. 45.
1
0.1021/ic00061a040.
5. Stewart, J.J.P., J. Comput.-Aided Mol. Des., 1990,
9
. Bosch, H.W. and Wayland, B.B., J. Chem. Soc., Chem.
Commun., 1986, no. 12, p. 900. DOI: 10.1039/
C39860000900.
vol. 4, no. 1, p. 1. DOI: 10.1007/BF00128336.
6. Zhou, X., Wang, R.-J., Mak, T.C.W., and Chan, K.S.,
Inorg. Chim. Acta, 1998, vol. 270, nos. 1–2, p. 551.
DOI: 10.1016/S0020-1693(97)05825-8.
1
1
1
1
0. Guilard, R. and Kadish, K.M., Chem. Rev., 1988,
vol. 88, no. 7, p. 1121. DOI: 10.1021/cr00089a007.
2
7. Lomova, T.N., Zaitseva, S.V., Molodkina, O.V., and
Ageeva, T.A., Russ. J. Coord. Chem., 1999, vol. 25,
no. 6, p. 397.
1. Kimata, S. and Aida, T., Tetrahedron Lett., 2001, vol. 42,
no. 25, p. 4187. DOI: 10.1016/S0040-4039(01)00685-2.
2. Collman, J.P. and Boulatov, R., J. Am. Chem. Soc.,
2
2
8. Granovsky, A.A., Gamess. http://classic.chem.msu.su/
2000, vol. 122, no. 48, p. 11 812. DOI: 10.1021/ja001364u.
gran/gamess/index.html.
3. Kadish, K.M., Hu, Y., Tagliatesta, P., and Boschi, T.,
9. Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T.,
Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N.,
Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and
Montgomery, J.A., Jr., J. Comput. Chem., 1993, vol. 14,
no. 11, p. 1347. DOI: 10.1002/jcc. 540141112.
Inorg. Chem., 1993, vol. 32, no. 14, p. 2996. DOI:
1
0.1021/ic00066a007.
1
1
1
4. Grass, V., Lexa, D., Momenteau, M., and Seveant, J.M.,
J. Am. Chem. Soc., 1997, vol. 119, no. 15, p. 3536. DOI:
1
0.1021/ja964023i.
3
3
0. http://www.chemcraftprog.com/index.html.
5. Vitols, S.E., Friesen, D.A., Williams, D.S., Melamed, D.,
and Spiro, T.G., J. Phys. Chem., 1996, vol. 100, no. 1,
p. 207. DOI: 10.1021/jp952003h.
1. Porfiriny: struktura, svoistva, sintez (Porphyrins:
Structure, Properties, and Synthesis), Enikolopyan, N.S.,
Ed., Moscow: Nauka, 1985.
6. Wayland, B.B., Vanvoorhees, S.L., and Del Rossi, K.J.,
3
2. Comprehensive Organic Chemistry, Barton, D. and
J. Am. Chem. Soc., 1987, vol. 109, no. 21, p. 6513. DOI:
Ollis, W.D., Eds., Oxford: Pergamon, 1979, vols. 1, 4.
1
0.1021/ja00255a048.
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