Some novel organometallic MnIII complexes with porphine and 1,6-diaminohexane

Article abstract of DOI:10.1134/S0036023616020212

A novel series of Mn^III complexes with 5,10,15,20-tetra(p-tolylporphine) and 1,6-diaminohexane has been synthesized. These complexes have been characterized by UV/Vis, IR, ESI-mass spectra, elemental analysis, conductivity and magnetic suscepti

Full text of DOI:10.1134/S0036023616020212

ISSN 0036-0236, Russian Journal of Inorganic Chemistry, 2016, Vol. 61, No. 2, pp. 232–238. © Pleiades Publishing, Ltd., 2016.
PHYSICAL METHODS
OF INVESTIGATION
Some Novel Organometallic MnIII Complexes
with Porphine and 1,6-Diaminohexane1
Shashi Lata Bharatia, Pankaj Kumar Chaurasiab, and Sudha Yadavab
aDepartment of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, Arunachal Pradesh, India
bDepartment of Chemistry, D.D.U. Gorakhpur University, Gorakhpur-273009, U.P. India
e-mail: shashilatachem@gmail.com
Received February 16, 2015
Abstract—A novel series of MnIII complexes with 5,10,15,20-tetra(p-tolylporphine) and 1,6-diaminohexane
has been synthesized. These complexes have been characterized by UV/Vis, IR, ESI-mass spectra, elemental
analysis, conductivity and magnetic susceptibility measurements. These MnIII porphyrins exhibited a blue
shift in soret band in comparison to non-metallated porphyrins. The molar conductance values of these com-
plexes show their non-electrolytic nature in ethanol. The tentative structures have also been proposed. All the
complexes have good level of water solubility due to which they may have medicinal as well as other valuable
biological applications.
Keywords: MnIII porphyrins,1,6-diaminohexane, 5,10,15,20-tetra(p-tolylporphine) ligand, ESI-mass spectra
DOI: 10.1134/S0036023616020212
plexes are soluble to water upto 40–60% only. Keeping
the above views in mind we have synthesized new
MnIII complexes with 5,10,15,20-tetra(p-tolylpor-
phine) ligand and 1,6-diaminohexane as an axial ligand
to observe in which way these ligands change the prop-
erties of previous reported MnIII porphyrins. In this
communication the synthesis and characterization of
these novel MnIII porphyrins have been reported.
Metalloporphyrins can experience reversible redox
reactions in which the site of electro transfer may be
localized at either the central metal or the porphyrin
ring [1]. Due to strong complexing properties and cat-
alytic behavior of metalloporphyrins these compounds
have found numerous applications in chemical analy-
sis [2]. The use of metalloporphyrins as catalysts in
oxidation reactions, like epoxidation of olefins,
hydroxylation of saturated hydrocarbon, has been
reported previously [3–9]. The MnIII Porphyrins have
several interesting aspects of physical, chemical and
biological properties which distinguish them from
other metalloporphyrins [10–12]. There has been
growing interest [13, 14] in MnIII porphyrins because
of their reactivity and accessibility of several oxidation
states that can be used for redox cycles useful for bio-
chemical applications. They hold a special place in
modern chemistry functioning as reaction catalysts,
oxygen transporters, chemical sensors [15, 16], anti-
cancer pharmaceutical drugs [17] or in molecular elec-
tronic devices [18]. MnIII porphyrins using 5,10,15,20-
tetra-phenylporphines have been studied extensively
[19–21].
EXPERIMENTAL
Materials and Physical Measurements
All the chemicals were A.R. Grade and have been
purified and dried whenever necessary by the standard
methods as given in literature [22–24]. Pyrrole was
purchased from Merck (Germany) and acetylacetone
from s.d-fine chemicals (Mumbai). Pyrrole and acet-
yleacetone have been used freshly distilled. Milli-Q
water has been used throughout the experimental pro-
cedures. The complexes were analysed using standard
procedures [25]. The elemental analyses have been
done from Cochin University of Science and Technol-
ogy, Cochin. Conductivity measurements were carried
out on century digital conductivity meter; model CC-601
with 10–3 M concentration in ethanol at room tem-
perature. Electronic spectra were recorded on Hitachi
(Japan) model U-2000 from 200–1100 nm in metha-
nol, using 1 mL quartz cuvette. IR spectra were
recorded on Perkin-Elmer (model-557) Beckman-
Acculab-10. The magnetic susceptibility measure-
ments were carried out at room temperature using EV7
In order to demonstrate different biological appli-
cability of these types of MnIII complexes, it is neces-
sary for them to be dissolved in water to greater
extents. If such complexes are found to be dissolved in
water then its utility in biological as well as medicinal
area will be enhanced. Our previously reported com-
1
The article is published in the original.
232

SOME NOVEL ORGANOMETALLIC MnIII COMPLEXES WITH PORPHINE
233
These [MnIII(TTP)X] complexes were dissolved in
ethanol and refluxed with 1,6-diaminohexane to give
[MnIII(TTP)X(dah)]. The proposed reaction scheme
may be given as below:
VSM (ADE-DMS-USA) Vibrating Sample Magne-
tometer from IIT, Kanpur. ESI-mass spectra were
recorded on WATERS-Q-T of premier-HAB213 using
ethanol as a solvent, from IIT Kanpur. Purity of the
complexes were checked by TLC plates, using silica gel
adsorbent and CH2Cl2/CH3OH in 1 : 4 ratio.
[MnIII(TTP)X] + dah
EtOH 42−46 h
Synthesis
Preparation of MnIII Porphyrins, [MnIII(TTP)X].
The ligand, 5,10,15,20-tetra(p-tolylporphine) has
been synthesized by literature method [26]. The syn-
thesis of MnIII-porphyrins have been carried out by
adopting a combined literature methods [27, 28]. The
[MnIII(TTP)X(dah)]
Where dah = 1,6-diaminohexane.
All these complexes were soluble in ethanol, meth-
anol, pyridine, chloroform, DMSO, DMF and mod-
erately (70%) soluble in water. The molar conduc-
bis(acetylacetonato) MnIII complexes with axial halo-
−
or pseudohalo groups i.e. Cl–, Br–, NCS– or
serve tance values of these complexes in ethanol with 10–3 M
N3,
concentration, are in the range of 7–15 Ω–1 cm2 mol–1,
indicating their non-electrolytic nature [30]. Physical
properties of these complexes have been given in Table 1.
as useful synthetic intermediates for the synthesis of
MnIII-porphyrins [29].
For preparation of [MnIII(TTP)Cl], 1.50 g
(0.005 mol) of chlorobis(acetylacetonato) MnIII and
3.5 g. (0.005 mol) of H2TTP were dissolved in 210 mL
of A.R. grade glacial acetic acid containing 60 mL of
acetic anhydride and refluxed it for for 4 h. After reflux-
ing, it was evaporated on steam-bath. The resulting
bright green complex was dried under vacuum over
P2O5. Recrystallization was done with 1 : 1 ratio of
chloroform and methanol and then air dried. The
yield was 3.93 g (78.56%). The Other complexes were
prepared analogously. All these complexes are non-
hygroscopic in nature.
Preparation of 1,6-diaminohexane complexes,
[MnIII(TTP)X(dah)]. For preparation of chloro complex,
0.759 g (0.001 mol) of [MnIII(TTP)Cl] was dissolved
in 4 mL of ethanol and then added 1.8 g (0.015 mol) of
1,6-diaminohexane. The whole content was stirred for
25 min at room temperature and refluxed for 46 h. The
reaction mixture was cooled at room temperature for
1 h and dried under vacuum over P2O5. Recrystalliza-
ton was done with ethanol. Yield was 0.667 g
(76.32%). The other complexes were prepared under
similar conditions.
IR Spectra
IR spectra of these complexes shows a medium
band at ~1326 cm–1 for ν(C=N–) which appears at
1350 cm–1 in the free ligand, this downward shift of
~25 cm–1 is due to co-ordination of porphine ligand
with metal. A sharp band at ~1622 cm–1 suggests
ν(C=C)pyrrole. Other medium bands at ~1179 and
~1571 cm–1 indicate ν(C–N) and ν(C=C)phenyl
respectively. A broad band at ~3020 cm–1 shows ν(C–
H)phenyl. A sharp band at ~980 cm–1 indicates (C–H)
rocking mode of pyrrole. All these bands of porphyrin
are in good agreement with literature values [31]. The
spectra of thiocyanato-tetra(p-tolylporphinato) MnIII
shows two characteristics bands of co-ordinated NCS–,
ν(C–S) at ~836 cm–1 and ν(C–N) at ~2070 cm–1. The
observed value at 836 cm–1 falls in the region expected
for N-bonded NCS– (860–780 cm–1) [32], confirm-
ing the NCS– co-ordinated through N. Two charac-
teristics peaks are observed in the azido-tetra(p-tolyl-
porphinato) MnIII complex for co-ordinated azide
group assigned as νasy(N–N) showing strong absorp-
tion at 1252 cm–1 which usually appears from 1340–
1181 cm–1 and another peak at ~2025 cm–1, indicating
coordination of azide group [33]. All these MnIII-por-
phyrins exhibit a medium band between 437–492 cm–1
for ν(Mn–N) [34, 35].
RESULTS AND DISCUSSION
The MnIII complexes with porphine ligand were
synthesized by the following reaction scheme:
[MnIII(acac2)X] + H2TTP
The ν(NH2) of 1,6-diaminohexane are at ~3422
Gla. Acetic acid
containing acetic
anhydride
and ~3315 cm–1 for free and co-ordinated amine
group respectively. Characteristic bands of diamines
appear between 1400–700 cm–1. A strong band is observed
at ~1325 cm–1 assigned to ω(NH2). The CN stretch of all
4 h
[MnIII(TTP)X]
uncomplexed diamines are at 1090–1070 cm–1 [36]. In
these newly synthesized complexes, bands are at
1055–1046 cm–1. This shift indicates co-ordination of
Where acac = acetylacetonato ligand
−
–
–
N
X = Cl , Br ,
, or NCS–
3
H2TTP = 5,10,15,20-tetra(p-tolylporphine) ligand.
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SHASHI LATA BHARATI et al.
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SOME NOVEL ORGANOMETALLIC MnIII COMPLEXES WITH PORPHINE
Table 2. Selected IR spectral results (cm-1) of MnIII-porphyrins
235
Mn(TTP)N3
Mn(TTP)Cl
Mn(TTP)Br
Mn(TTP)NCS
Assignment
490
1606
1304
1183
1520
3021
1440
–
492
1604
1306
1181
1518
3022
1442
–
488
1608
1304
1184
1515
3023
1440
–
491
1604
1308
1184
1518
3022
1443
2070
–
ν(Mn–N)
ν(C=C) py
ν(C=N)py
ν(C–N)py
ν(C=C) ph
ν(C–H)ph
νantisym(C–H) of CH3
ν(NCS)
–
–
2025
ν(N3)
Table 3. Selected IR spectral results (cm–1) of MnIII-porphyrins
[Mn(TTP)N3(dah)]
[Mn(TTP)Cl(dah)]
[Mn(TTP)Br(dah)]
[Mn(TTP)NCS(dah)]
Assignment
475
473
473
1610
1325
1170
1512
3028
1423
–
475
1610
1328
1170
1510
3030
1425
2073
–
ν(Mn–N)
1613
1611
ν(C=C)py
1323
1328
ν(C=N)
1168
1168
ν(C–N)
1512
1510
ν(C=C)ph
3028
3029
ν(C–H)ph
1425
1423
νantisy(C–H) of CH3
ν(NCS)
–
–
–
3325
–
3323
2023
3323
3421
ν(N3)
3325
3422
ν(NH2)co-ordinated
ν(NH2)unco-ordinated
3422
3421
[Mn(TTP)Cl(dah)]
[Mn(TTP)Br(dah)]
[Mn(TTP)N3(dah)] [Mn(TTP)NCS(dah)] Assignment
with λmax(nm) at 666, 665, 678, 666 for X = Cl–, Br–,
and NCS– respectively [38, 39] (Table 4). The
intense band at 445–460 nm in electronic spectra of
these complexes are assigned to charge transfer band
from a1u(π) and a2u(π) orbital of porphyrin to eg(dπ)
orbital of manganese [40–42].
diamines nitrogen to manganese. The NH2 rocking
mode is a strong band at ~635 cm–1. The ν(C–C) has
been assigned as a strong band at ~1000 cm–1 [37]. The
above data indicates that 1,6-diaminohexane co-ordi-
nates as an unidentate ligand to MnIII (Tables 2, 3).
N3−
Electronic Spectra
The ligand field parameters i.e. 10Dq, B and β have
also been calculated for these MnIII-porphyrins. The
value of 10Dq have been calculated from λmax at maxi-
mum absorbance. The value of B has been calculated
by using the formula Dq/B = 2.7 using the Tanabe–
Sugano diagram while β has been calculated using the
formula
Electronic spectra of the porphyrins exhibit an
intense band near 400 nm that are assigned as soret or
B band. Several weaker absorptions also occur near
480–700 nm which are known as Q bands.
For [MnIII(TTP)X] complexes, the B band appear
with λmax(nm) at 455, 453, 450 and 452 and Q bands
with λmax(nm) at 648, 644, 642 and 645, while for
[MnIII(TTP)X(dah)] complexes, the B band appear
with λmax(nm) at 449, 445, 460 and 455 and Q bands
β = Bin complex/Bfree ion
.
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SHASHI LATA BHARATI et al.
Table 4. UV-visible spectroscopic data of free base porphy- Table 5. Different ligand field parameters calculated for dif-
rin and MnIII-porphyrins
Ligand/complexes
ferent MnIII-porphyrins
Complexes
10Dq (cm–1) B (cm–1)
λmax (nm)
β
Soret (B)
band
[Mn(TTP)Cl]
[Mn(TTP)Br]
[Mn(TTP)N3]
21978
22075
22022
22123
23923
25000
22042
23570
814
815
822
819
885
925
816
872
0.71
0.71
0.72
0.71
0.77
0.81
0.71
0.76
Q band
H2TTP
484
455
453
450
452
449
445
460
455
651
648
644
642
645
666
665
678
666
[Mn(TTP)NCS]
[Mn(TTP)Cl(dah)]
[Mn(TTP)Br(dah)]
[Mn(TTP)N3(dah)]
[Mn(TTP)NCS(dah)]
[Mn(TTP)Cl]
[Mn(TTP)Br]
[Mn(TTP)N3]
[Mn(TTP)NCS]
[Mn(TTP)Cl(dah)]
[Mn(TTP)Br(dah)]
[Mn(TTP)N3(dah)]
[Mn(TTP)NCS(dah)]
m/z at 670 for [C48H36N4 + 2H]+ molecular ion was
found for the complex [Mn(TTP)NCS(dah)].
Magnetic Susceptibility
The value of B are below the free ion value for
MnIII-ion (1140 cm–1) [43], this indicates the covalent
metal-ligand bonds in all these complexes, with the
covalency factor β varying in the range 0.71–0.81
(Table 5).
The magnetic susceptibility measurements show
that these complexes have μeff values in the range of
4.70–4.98 μB [47]. The presence of four unpaired
electrons indicates the high spin MnIII complexes with
porphyrins.
ESI-Mass Spectra
CONCLUSION
ESI-mass spectra was used for identity and purity
of these MnIII-porphyrins [44–46]. The different
molecular ion peaks found for different complexes and
data is given below: m/z at 723 for [C48H36N4Mn–Cl]+
The manganeseIII complexes with 5,10,15,20-
tetra(p-tolylporphine) ligand have been prepared for
the first time. On the basis of positions of ν(NH2) in
molecular ion, m/z 670 for [C48H36N4 + 2H]+ molec-
ular ion, for the complex [Mn(TTP)Cl], m/z at 724 for
[C48H36N4Mn + H]+ molecular ion, m/z at 670 for
[C48H36N4 + 2H]+ molecular ion for the complex
[Mn(TTP)Br], m/z at 723 for [C48H36N4Mn]+ molec-
ular ion, m/z at 670 for [C48H36N4 + 2H]+ molecular
ion for the complex [Mn(TTP)N3], and m/z at 724 for
[C48H36N4Mn + H]+ molecular ion, m/z at 670 for
[C48H36N4 + 2H]+ molecular ion for the complex
[Mn(TTP)NCS].
While m/z at 839 for [C54H52N6Mn–Cl]+ molecu-
lar ion, m/z at 725 for [C48H36N4Mn + 2H]+ molecu-
lar ion and m/z at 670 for [C48H36N4 + 2H]+ molecular
ion for the complex [Mn(TTP)Cl(dah)], m/z at 803
for [C48H36N4BrMn]+ molecular ion, m/z at 725 for
[C48H36N4Mn + 2H]+ molecular ion and m/z at 670
for [C48H36N4 +2H]+ molecular ion for the complex
[Mn(TTP)Br(dah)], m/z at 766 for [C48H36N7Mn +
H]+ molecular ion, m/z at 723 for [C48H36N4Mn]+
molecular ion and m/z at 670 for [C48H36N4 + 2H]+
molecular ion for the complex [Mn(TTP)N3(dah)]
and m/z at 781 for [C49H36N5SMn]+ molecular ion,
m/z at 724 for [C48H36N4Mn + H]+ molecular ion and
IR spectra of [MnIII(TTP)X(dah)] complexes, it was
concluded that 1,6-diaminohexane is co-ordinated to
MnIII as unidentate ligand. The ESI-mass spectra
indicates that these complexes are monomeric in
nature having octahedral geometry, while the
[MnIII(TTPX] complexes have square pyramidal
geometry as reported earlier [38, 39]. The previously
synthesized MnIII-porphyrins have shown depolymer-
isation activity towards Humic acid model compound,
in the same way these newly synthesized MnIII por-
phyrins can be studied for their depolymerisation
activity which can also be used as a feedstock for
preparation of commodity and rare chemicals. One
important finding of this manuscript is that all the
synthesized MnIII complexes of this manuscript are
soluble in water to much more extent in comparison to
our previously synthesized complexes (~70%) which
may be valuable from the points of view of their bio-
logical studies. Studies of biological and medicinal
importance on the basis of their solubility in water are
in progress.
ACKNOWLEDGMENTS
Dr. Shashi Lata Bharati is grateful to Department
of Chemistry, DDU Gorakhpur University, Gorakh-
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SOME NOVEL ORGANOMETALLIC MnIII COMPLEXES WITH PORPHINE
CH3
237
X
N
N
N
Mn(III)
CH3
H3C
N
CH3
III
Fig. 1. [Mn (TTP)X] complexes.
CH3
X
N
N
N
Mn(III)
CH3
H3C
N
dah
CH3
III
Fig. 2. [Mn (TTP)X(dah)] complexes.
2. M. Biesaga, K. Pyrzynska, and M. Trojanowicz,
pur for the award of UGC-DSA fellowship during her
Ph.D. The academic support of Prof. V.K. Yadav and
Prof. S.S. Manoharan, Department of Chemistry, IIT
Kanpur, for recording ESI-mass spectra and magnetic
susceptibility measurements, respectively, is gratefully
acknowledged.
Talanta 51, 209 (2000).
3. Meunier B., Chem Rev. 92, 1411 (1992).
4. Quici S., Banafi S., Pozzi G., Gazz. Chim. Ital., 123,
597 (1993).
5. Mansuy D., Pure Appl. Chem. 66, 737 (1994).
6. Metalloporphyrins in Catalytic Oxidations, Ed. by
REFERENCES
R. A. Sheldon (Marcel Dekker, New York, 1994).
1. S. Jeon H. K. Lee, and Yong-Cook Chai, Bull. Korean
7. Metalloporphyrins Catalysed Oxidations, Ed. by F. Mon-
Chem. Soc. 17, 929 (1996).
tanari and L. Casella (Kluwer, Dordrecht, 1994).
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 61 No. 2 2016

238
SHASHI LATA BHARATI et al.
8. A. M. R. Gonsalves and M. M. Pereira, J. Mol. Catal. 28. B. R. Stults, V. W. Day, E. L. Tassett, and R. S. Mari-
A: Chem. 113, 209 (1996). anelli, Inorg. Nucl. Chem. Lett. 9, 1259 (1973).
9. D. Dolphin, T. G. Traylor, and L. Y. Xie, Acc. Chem. 29. B. R. Stults, V. W. Day, and R. S. Marianelli, Inorg.
Res. 30, 251 (1997). Chem. 14, 722 (1975).
10. B. M. Hoffman, C. J. Weschler, and F. Basolo, J. Am. 30. S. F. A. Kettle, Coordination Compounds (Nelson, Pit-
Chem. Soc. 100, 4416 (1978). man Press, London, 1975).
11. A. Harriman, J. Chem. Soc, Dalton Trans., 141 (1984). 31. D. W. Thomas and A. E. Martell, J. Am. Chem. Soc.
78, 1338 (1956).
12. T. Jin, T. Suzuki, T. Imamura, and M. Fujimoto, Inorg.
Chem. 26, 1280 (1987).
32. R. J. H. Clark and C. S. Williams, Spectrochim. Acta
22, 1081 (1966).
13. L. F. Lauffer, Chem. Rev. 87, 901 (1987).
33. J. R. Dyer, Applications of Absorption Spectroscopy of
Organic Compounds (Prentice-Hall of India Private,
New Delhi, 1969).
14. M. Ravikanth and T. K. Chandrashekhar, Struc. Bond.
82, 105 (1995).
15. E. Malinowaska, J. Niedziolka, and M. E. Meyerhoff,
34. T. N. Lomova and B. D. Berezin, Russ. J. Coord.
Anal. Chim. Acta 432, 67 (2001).
Chem. 27, 85 (2001).
16. D. Vlascici, E. Fagadar-Cosma, and O. Bizerea-
35. G. Wilkinson, R. D. Gillard, and J. A. McCleverty,
Comprehensive Coordination Chemistry (Pergamon,
Oxford, 1987), Vol. 1, p. 816.
Spirido, Sensors 6, 892 (2006).
17. H. Brunner and K. M. Schellerer, Monatch. Chem.
133, 679 (2002).
36. I. Gamo, Bull. Chem. Soc. Jpn. 34, 760 (1961).
18. C. M. Drain, J. T. Hupp, K. S. Suslick, et al., J. Porph.
37. A. D. Allen and C. V. Senoff, Can. J. Chem. 45, 888
Phthal. 6, 243 (2002).
(1965).
19. Day V.W., Stults B.R., Tassett E.L., et al., J. Inorg.
38. S. Yadava and S. L. Bharati, J. Coord. Chem. 64, 3950
Nucl. Chem. Lett. 11, 505 (1975).
(2011).
20. A. Tulinsky and B. M. L. J. Chen, J. Am. Chem. Soc.
39. S. Yadava and S. L. Bharati, J. Coord. Chem. 65, 3492
197799, p. 3647.
(2012).
21. J. F. Kirner and W. R. Scheidt, Inorg. Chem. 14, 2081
40. E. Fagadar-Cosma, M. C. Mirica, I. Balcu, et al., Mol-
(1975).
ecules, 14, 1370 (2009).
22. R. J. Errington, Advanced Practical Inorganic and
Metalloorganic Chemistry, 1st Ed. (Chapman and Hall,
London, 1997).
23. W. L. F. Armarego and D. D. Perrin, Purification of
Laboratory Chemicals, 4th Ed. (Butterworth-Heine-
mann, Oxford, 1997).
24. B. S. Furniss, A. J. Hannaford, V. Rogers, et al., Vogel’s
Text Book of Practical Organic Chemistry, 4th Ed.
(ELBS, London, 1984).
41. Y. Lamamoto, M. D. Assis, K. J. Ciuffi, et al., J. Mol.
Catal. A: Chem. 116, 365 (1997).
42. H. A. O. Hill, A. J. MacFarlane, and R. J. P. Williams,
J. Chem. Soc., 1704 (1969).
43. J. E. Huheey, E. A. Keiter, and R. L. Keiter, Inorganic
Chemistry, Principles of Structure and Reactivity, 4th Ed.
(Pearson Education, Singapore, 2005).
44. I. Batinic-Haberle, I. Spasojevic, R. D. Stevens, et al.,
Dalton Trans., 617 (2006).
25. G. H. Jeffery, J. Bassett, J. Mendham, and R. C. Denny,
Vogel’s Text Book of Quantitative Chemical Analysis, 45. I. Batinic-Haberle, I. Spasojevic, R. D. Stevens, et al.,
5th Ed. (ELBS, London, 1996).
26. A. D. Adler, F. R. Longo, J. D. Finarelli, et al., J. Org. 46. I. Batinic-Haberle, I. Spasojevic, R. D. Stevens, et al.,
Chem. 32, 476 (1967). Dalton Trans. 1696 (2004).
27. E. B. Fleischer, J. M. Palmer, T. S. Srivastava, and A. 47. D. V. Behere and S. Mitra, Inorg. Chem. 19, 992
Chatterjee, J. Am. Chem. Soc., 93, 3163 (1971). (1980).
J. Chem. Soc., Dalton Trans. 2689 (2002).
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