Reaction of small molecules O2, NO, CO, and the Naldini salt (PPh3)2MnBr2: Characterized by infrared spectroscopy, elemental analysis, and single-crystal X-ray diffraction

Article abstract of DOI:10.1002/jccs.201900463

Addition of 2 equiv. of PPh₃ to MnBr₂ in tetrahydrofuran (THF) solution under N₂ atmosphere results in the formation of Naldini salt (PPh₃)₂MnBr₂ (1). Reaction of Complex 1 and O₂

Full text of DOI:10.1002/jccs.201900463

Received: 30 October 2019
DOI: 10.1002/jccs.201900463
Revised: 26 November 2019
Accepted: 26 November 2019
S P E C I A L I S S U E P A P E R
Reaction of small molecules O2, NO, CO, and the Naldini
salt (PPh3)2MnBr2: Characterized by infrared spectroscopy,
elemental analysis, and single-crystal X-ray diffraction
Bo-Wei Huang1 | Minh-Trung Nguyen1,2 | Chung-Hung Hsieh1
1Department of Chemistry, Tamkang
Abstract
University, New Taipei City, Taiwan
2Department of Biology, Faculty of
Natural Science and Technology, Tay
Nguyen University, Buon Ma Thuot City,
Vietnam
Addition of 2 equiv. of PPh3 to MnBr2 in tetrahydrofuran (THF) solution under
N2 atmosphere results in the formation of Naldini salt (PPh3)2MnBr2 (1). Reac-
tion of Complex 1 and O2, NO, and CO (with reducing agent) leads to Complex
(OPPh3)2MnBr2 (2), (PPh3)2Mn(NO)Br2 (3), and (PPh3)2Mn(CO)3Br (4), respec-
tively. Both Complexes 2 and 4 crystallize in the triclinic space group P-1 with
a = 9.94 Å, b = 10.11 Å, c = 10.53 Å; α = 65.42ꢀ, β = 63.16ꢀ, and γ = 89.22ꢀ of
2 and a = 10.23 Å, b = 12.26 Å, c = 14.44 Å and α = 97.03ꢀ, β = 104.34ꢀ, and
γ = 106.33ꢀ of 4. The isoelectronic replacement of 3CO with 2NO yields the
{Mn(NO)2}8 species (PPh3)2Mn(NO)2Br (5). The single crystal of 5 is in the
monoclinic space group C2/c with a = 23.17 Å, b = 9.62 Å, c = 15.92 Å, and
β = 114.91ꢀ. In the THF solution, Complex 5 serves as an NO source in the
presence of NO trapping, Co(TPP), Co(TPP) = 5,10,15,20-tetraphenyl-
21H,23H-porphine cobalt(II).
Correspondence
Chung-Hung Hsieh, Department of
Chemistry, Tamkang University, New
Taipei City 25137, Taiwan.
Email: chsieh@mail.tku.edu.tw
Funding information
Ministry of Science and Technology,
Taiwan, Grant/Award Number: MOST
107-2113-M-032-001-; 105-2113-M-
032-004-MY2
K E Y W O R D S
bromide, carbon monoxide, manganese, Naldini salt, nitric oxide, oxygen, triphenyl phosphine
1 | INTRODUCTION
quantum yields (PLQYs).[4] These manganese complexes
are simple to synthesize and have a stable structure, bipo-
The Naldini salt (PPh3)2MnBr2 (1) was first prepared
under the air and ambient condition in 1960.[1] However,
the reaction product was considered to be an oxygenated
and unoxygenated mixture based on elemental analy-
sis.[2] The preparation was then improved by Dumitru in
1965. The stoichiometric portions of MnBr2 and PPh3
were dissolved in dried, freshly distilled THF and then
refluxed for 4 hr under nitrogen to generate Complex
1 (Equation 1).[3]
In a recent study, the triphenyl phosphine ligand of
Naldini salt was modified to several dibenzofuran-based
phosphines. These unique derivatives exhibit intense
green phosphorescence with high photoluminescence
lar characteristics, and good photo physics properties,
which reduce the manufacturing cost of the luminescent
material and can replace the precious metal ruthenium
complex as the luminescent layer material to prepare the
organic light-emitting diode.[4]
Also in the biological system, the manganese com-
plexes were involved in the light-dependent reaction of
oxygenic photosynthesis (photosystem II) and are known
as the oxygen-evolving center (OEC). Photosynthetic
water splitting to generate molecule oxygen was cata-
lyzed by four manganese-oxo units with an OEC, which
may contribute to effective sunlight as an alternative
energy source and O2 for human daily use.[5]
© 2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2019;1–6.
http://www.jccs.wiley-vch.de
1

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HUANG ET AL.
The reaction/activation of small molecules (H2, N2,
from bright yellow to orange in about 5 min (Scheme 1b).
The reaction product was identified by FT-IR (ν(NO): 1,737 s
cm−1), which was assigned as a mononitrosyl complex
(PPh3)2Mn(NO)Br2 (3) with {Mn(NO)}6 electronic configura-
tion according to the Enemark-Feltham notation.[8]
No reaction occurred when CO gas was bubbled into
the THF solution of Complex 1, which may be attributed
to the lack electron density of the MnII center, partially
transferred from a d-orbital of the metal to antibonding
O2, NO, N2O, CO2, CO, and CH4) by metal-mediated
binding has been the highlight of fundamental chemistry
in the past 10–15 years,[6] but little is known about the
reactivity of these small molecules and the Naldini salt in
the literature.[1–3] Here, we have examined the character-
istics of O2, NO, and CO toward the Naldini salt (PPh3)
2MnBr2 (1).
2 | RESULTS AND DISCUSSION
TABLE 1 Selected bond distances (Å) and angle (deg) for
Complexes 2, 4, and 5
The Naldini salt (PPh3)2MnBr2 (1) was prepared using an
improved procedure. Complex 1 is a bright yellow solid
with good solubility in the THF or CH2Cl2 at room tem-
perature. Reaction of Complex 1 and freshly prepared O2
gas in the THF solution leads to the formation of greenish
yellow Complex (OPPh3)2MnBr2 (2) (Scheme 1a). The sin-
gle crystal of Complex 2 was obtained by slow diffusion of
the diethyl ether/hexanes solution into a concentrated
THF solution at 0ꢀC. Full crystallographic data of Complex
2 are shown in Tables S1 and S2, and the selected bond
lengths and angles are listed in Table 1. Greenish yellow
crystals of 2 are stable in the air. The structure was first
published in 1966 in the monoclinic system, with
a = 24.33, b = 14.33, c = 13.18 Å, and β 93ꢀ; Z = 7.[7] In
this work, the triclinic system was observed with a = 9.94,
b = 10.11, c = 10.53 Å and α = 65.4ꢀ, β = 63.2ꢀ, γ = 89.2ꢀ;
Z = 1. The distorted tetrahedral geometries in both struc-
tures are largely the same (Figure 1)
2
4
5
Mn-PPh3avg.
Mn-OPPh3avg.
Mn-Br.
—
2.323(5)
—
2.329(6)
2.389(4)
—
2.4739(14)a
2.496(7)
2.4838(14)
—
Mn-COavg.
—
1.7174(19)
—
Mn-NOavg.
—
—
1.687(8)
164.70(4)
—
∠Ph3P-Mn-PPh3
∠O-Mn-O
176.48(2)
100.89(17)
—
—
∠OC-Mn-COavg.
175.7(2)b
89.5(2)c
—
∠ON-Mn-NO
∠Mn-N-Oavg.
—
—
120.00(16)
174.6(7)
Note: The maximum deviations from the average distances and angles are
shown in the table.
aThe average distance of Mn-Br.
bThe angle of trans-CO.
cThe average angle of cis-CO. Full lists of metric parameters are given in
In the reaction of Complex 1 and freshly prepared NO
gas in the THF solution, the color of the solution turned
the SI.
FIGURE 1 View of the thermal ellipsoid plot at 50%
probability of Complex 2. Hydrogen atoms have been removed for
clarity. Full metric data of Complex 2 are listed in the Supporting
Information
SCHEME 1 Reaction of (PPh3)2MnBr2 (1) and O2, NO,
and CO

HUANG ET AL.
3
SCHEME 2 Reaction of (PPh3)2Mn(CO)3Br (4) and NO
FIGURE 2 View of the thermal ellipsoid plot at 50%
probability of Complex 4. Hydrogen atoms have been removed for
clarity. Full metric data of Complex 4 are listed in the Supporting
Information. The site occupancy factor of the Br1 and the C1O1
groups in Complex 4 is found at disordered positions (2/3:1/3)
molecular orbitals of CO.[9] Addition of the reducing
agent (sodium/benzophenone) in an equimolar portion of
1 under CO atmosphere in THF at room temperature over-
night results in the formation of complex (PPh3)2Mn(CO)3Br
(4) (Scheme 1c, FT-IR ν(CO): 1,950 vs, 1,916 w cm−1). Com-
plex 4 was isolated as a light orange semisolid, and single
crystals suitable for the X-ray analysis were obtained by
slow vaporization of the diethyl ether/hexanes mixed solu-
tion in the refrigerator. The structural determination data
are shown in the SI (Tables S2 and S3), and selected bond
lengths/angles are summarized in Table 1. The structure
of 4 is described as an octahedral with two PPh3 ligands
located in the trans- position of the MnI center (Figure 2).
Another synthetic option of Complex 4 is to react
Mn(CO)5Br and 2 equiv. of PPh3 in THF solution and
FIGURE 3 View of the thermal ellipsoid plot at 50%
probability of Complex 5. Hydrogen atoms have been removed for
clarity. Full metric data of Complex 5 are listed in the Supporting
Information. The site occupancy factor of the Br1 and the N1O1
groups in Complex 5 is found at disordered positions (1/2:1/2)
distorted trigonal bipyramidal (TBP) geometry is shown in
Figure 3. The structure is best described as two NO and
one bromide located in the equatorial and two PPh3 occu-
pying the axial position. Complex 5 was first synthesized
by Henri and Manfred in 1973, which was characterized as
an impurity from the reaction of [(C5H5) (PPh3)Mn(CO)
(NO)][PF6] and PhLi (where PhLi is prepared from PhBr)
and lack of X-ray structural evidence.[11] In this study, the
isoelectronic replacement of 3CO by 2NO is presented,
which leads to the formation of pure product 5. The Mn-
PPh3avg. and Mn-Br distances of Complex 5 are 2.329
(6) and 2.4838(14) Å, respectively, which are approximately
identical to Complex 4 (2.323(5) and 2.496(7) Å). The Mn-
NOavg. angle of 5 is close to linear (174.6(7)ꢀ). Therefore,
we assign the electronic configuration of 5 as a composition
of MnI and two NO radicals, that is, {MnI(•NO)2}8[8]
[10]
reflux under N2
We also test the reactivity of Complex 4 and NO gas.
The freshly prepared dried NO was bubbled into the solu-
tion until the reaction mixture turned from yellow to
orange (about 5 min) at ambient temperature (Scheme 2).
The FT-IR characterization (ν(NO): 1,712 m, 1,668 s cm−1
(THF)) was assigned to the formation of complex
(PPh3)2Mn(NO)2Br (5). Single crystals were obtained by
slow diffusion of the diethyl ether/hexane solution into a
concentrated THF solution of Complex 5 at −20ꢀC. The full
crystal data of 5 are shown in the SI (Tables S4 and S5),
and selected bond distances and angles are listed in
Table 1. The ORTEP plot of five coordinate Complex 5 with
To probe the ability of the Dinitrosyl Manganese Com-
plex 5 (DNMC 5) to release or transfer NO, the DNMC 5 was
combined with 2 equiv. of NO trapping reagent Co(TPP),
Co(TPP) = 5,10,15,20-tetraphenyl-21H,23H-porphine
cobalt(II)), in THF solution. Coupled with an almost

4
HUANG ET AL.
immediate color change, the FT-IR band that grew at
1,683 cm−1, concomitant with the loss of NO bands from the
DNMC 5, indicated (NO)Co(TPP) formation (Equation 2).[12]
This reactivity of the {Mn(NO)2}8 DNMC 5 was consistent
with the oxidized {Fe(NO)2}9 Dinitrosyl Iron Complexes,
DNICs, which showed NO-releasing ability upon mixing
with THF solutions of Co(TPP).[13] The preliminary result of
this study suggests that DNMC in the {Mn(NO)2}8 oxidation
level is able to act as a 2NO donor in the presence of a suit-
able NO-trapping agent. Nevertheless, the mechanism of NO
transfer is unknown, similar to the fate of the DNIC follow-
ing loss of NO.[14]
3.1.2 | Reaction of Complex 1 and NO
A 50 ml Schlenk flask was loaded with Complex
1 (0.296 g，0.4 mmole) and dissolved in THF (10 ml).
The freshly prepared dried NO was bubbled until the
mixed solution turned from light yellow to orange (about
5 min) at ambient temperature. The product was identi-
fied by FT-IR to confirm the formation of Complex
(PPh3)2Mn(NO)Br2 (3). The solution was filtered through
celite to separate the insoluble solid. After the resulting
solution was reduced under vacuum, diethyl ether and
hexanes (10 and 20 ml, respectively) were added to pre-
cipitate the solid and dried under vacuum to afford the
solid of Complex 3 (yield 0.189 g, 64%). The orange crys-
tals, suitable for single-crystal X-ray diffraction analysis,
were obtained by slow diffusion of the diethyl ether/hex-
anes solution into a concentrated THF solution of Com-
plex 3 in the refrigerator at −20ꢀC. IR ν(NO): 1,737 s
cm−1 (THF). Anal. Calcd. for C36H30Br2MnNOP2: C,
56.20; H, 3.93; N, 1.82. Found: C, 56.13; H, 4.10; N, 2.00
3 | EXPERIMENTAL
3.1 | Synthesis
Manipulations, reactions, and transfers were conducted
under nitrogen according to Schlenk techniques or in a
glovebox (nitrogen gas). Solvents were distilled under nitro-
gen from appropriate drying agents (diethyl ether, hexanes,
and tetrahydrofuran (THF) from sodium benzophenone)
and stored in dried, N2-filled flasks over 4 Å molecular
sieves. Nitrogen was purged through these solvents before
use. The solvent was transferred to the reaction vessel via
stainless cannula under positive pressure of N2. The
reagents MnBr2, triphenylphosphine (PPh3) (TCI), sodium,
and benzophenone (Sigma-Aldrich) and infrared spectra of
the carbonyl ν(CO) and ν(NO) stretching frequencies were
recorded on a Thermo iS5 FT-IR spectrophotometer. Ana-
lyses of carbon, hydrogen, and nitrogen were conducted
with a CHN analyzer (Heraeus)
3.1.3 | Reaction of Complex 1 and CO
with reducing agent Na/benzophenone
To a stirred solution of Complex 1 (0.296 g, 0.4 mmole) in
THF (15 ml) under CO(g) atmosphere at room tempera-
ture, a portion of Na/benzophenone THF solution (0.011 g
and 0.48 mmole of metal Na and 0.073 g of benzophenone
in 10 ml THF) was added dropwise by syringe. The reac-
tion solution was stirred for 10 hr at room temperature
and then dried under vacuum to afford the semisolid.
After diethyl ether and hexane (5 and 15 ml, respectively)
were added to dissolve the semisolid, the reaction mixture
was filtered through celite to remove the insoluble solid.
The filtrate was then dried under vacuum to afford the
light orange semisolid of complex (PPh3)2Mn(CO)3Br
(4) (yield 0.139 g, 47%). The light orange crystals, suitable
for single-crystal X-ray diffraction analysis, were obtained
by slow vaporization of the diethyl ether/hexanes solution
in the refrigerator at −20ꢀC. IR ν(CO): 1,950 vs
1,916 w/cm (THF). Anal. Calcd. for C39H30BrMnO3P2: C,
62.75; H, 4.46. Found: C, 63.01; H, 4.07
3.1.1 | Reaction of Complex
(PPh3)2MnBr2 (1) and O2
A 50 ml Schlenk flask was loaded with Complex 1 (0.296 g,
0.4 mmole) and dissolved in THF (10 ml). The freshly pre-
pared dried O2 was bubbled until the reaction mixture turned
from light yellow to greenish yellow (about 30 min) at ambi-
ent temperature. The solution was filtered through celite to
separate the insoluble solid. After the resulting solution was
reduced under vacuum, diethyl ether and hexanes (10 and
20 ml, respectively) were added to precipitate the solid and
dried under vacuum to afford the solid of Complex
(OPPh3)2MnBr2 (2) (yield 0.234 g, 76%). The greenish yellow
crystals, suitable for single-crystal X-ray diffraction analysis
were obtained by slow diffusion of the diethyl ether/hexanes
solution into a concentrated THF solution of Complex 2 in the
refrigerator at 0ꢀC. Anal. Calcd. for C36H30Br2Mn1O2P2: C,
56.06; H, 3.92. Found: C, 56.00; H, 3.75
3.1.4 | Reaction of Complex 4 and NO
A 50 ml Schlenk flask was loaded with Complex
4 (0.297 g，0.4 mmole) and dissolved in THF (10 ml).
The freshly prepared dried NO was bubbled into the solu-
tion until the reaction mixture turned from yellow to
orange (about 5 min) at ambient temperature. The prod-
uct was identified by FT-IR to confirm the formation of

HUANG ET AL.
5
Complex (PPh3)2Mn(NO)2Br (5). The solution was fil-
tered through celite to separate the insoluble solid. After
the resulting solution was reduced under vacuum, diethyl
ether and hexanes (10 and 20 ml, respectively) were
added to precipitate the solid and dried under vacuum to
afford the solid of Complex 5 (yield 0.189 g, 58%). The
dark orange crystals, suitable for single-crystal X-ray dif-
fraction analysis, were obtained by slow diffusion of the
diethyl ether/hexanes solution into a concentrated THF
solution of Complex 5 in the refrigerator at −20ꢀC. IR
ν(NO): 1,712 m, 1,668 s/cm (THF). Anal. Calcd. for
C36H30BrMnN2O2P2: C, 60.10; H, 4.20; N, 3.89. Found: C,
59.83; H, 3.98; N, 4.01
atoms. Hydrogen atoms were placed at idealized posi-
tions and refined with fixed isotropic displacement
parameters. The following is a list of programs used: data
collection and cell refinement, APEX2;[15] data reduc-
tions, SAINTPLUS Version 6.63;[16] absorption correc-
tion, SADABAS;[17] structural solutions, SHELXS-97;[18]
structural refinement, SHELXL-97;[19] and graphics and
publication materials, Mercury Version 2.3.[20] Full crys-
tal data have been submitted to the Chambridge Crystal-
lographic Data Centre (CCDC).
4 | CONCLUSIONS
We have synthesized the Naldini salt (PPh3)2MnBr2
(1) and reacted it with O2, NO, and CO. We have given
an account of the characterization of each product,
including the IR, elemental analysis, single-crystal X-ray
diffraction, and the NO transferring from DNMC 5 in the
presence of NO trapping agent Co(TPP). This study may
provide information for sensing/releasing of these gas
molecules for future applications.
3.1.5 | NO trapping experiments
Orange Complex 5 was formed in situ according to the pro-
cedure described above (0.05 mmole) and transferred via a
cannula to a Schlenk flask containing Co(TPP) (0.067 g,
0.1 mmole in 10 ml of THF, Co(TPP) = 5,10,15,20-
tetraphenyl-21H,23H-porphine cobalt(II)).Within minutes,
an FT-IR absorption band at 1,683 cm−1 assignable to (NO)
Co(TPP) appeared and continued to grow over the course
of 2 hr, along with a distinct color change of the solution
from dark orange-red to red. A decrease of Complex 5 FT-
IR bands at 1,712 and 1,668 cm−1 and an increase of the
band at 1,683 cm−1 were considered an indication of NO
transfer[12,13]
ACKNOWLEDGMENTS
This work was supported by the Ministry of Science and
Technology, Taiwan (MOST 107-2113-M-032-001-;
105-2113-M-032-004-MY2). We thank Dr. Gene-Hsiang
(Instrumentation Canter, National Taiwan University)
for the discussions of crystallographic analyses.
ORCID
3.2 | Crystallography
Chung-Hung Hsieh https://orcid.org/0000-0003-1509-
8146
Crystallographic data and structure refinements param-
eters of Complexes 2, 4, and 5 are summarized in the
Supporting Information (Tables S1–S6). The crystals of
Complexes 2, 4, and 5 chosen for X-ray diffraction stud-
ies are measured in sizes of 0.30 × 0.03 × 0.3 mm,
0.12 × 0.10 × 0.04 mm, and 0.09 × 0.03 × 0.02 mm,
respectively. Each crystal was mounted on a glass fiber
and quickly coated in epoxy resin. Unit-cell parameters
were obtained by least-squares refinement. Diffraction
measurements for Complexes 2, 4, and 5 were carried
out on a Bruker SMART Apex CCD diffractometer
using graphite-monochromated Mo Kα radiation
(λ = 0.7107 Å), with values between 3.60ꢀ and 28.34ꢀ
for Complex 2, between 2.54ꢀ and 2,747ꢀ for Complex
4, and between 3.33 and 28.34ꢀ for Complex 5. The
space groups were determined on the basis of system-
atic absences and intensity statistics. The structures
were solved by direct methods and refined by full-
matrix least-squares on F2. Anisotropic displacement
parameters were determined for all nonhydrogen
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synthesis/isolation of bioactive complexes and drug
target development.
Chung-Hung Hsieh is a Taiwanese,
with a Ph.D. from the National Tsing
Hua University, Taiwan. Following
as associated research scantiest at
Taxes A&M University, College Sta-
tion, USA, he joined the faculty at
Department of Chemistry, Tamkang
[20] C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock,
G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl.
Crystallogr. 2006, 39, 453.
University, Taiwan, in 2013. Trained as
a
bioorganometallic chemist, his research focuses on
the small molecules (H2O, O2, CO, NO or H2) activa-
tion via organometallic compounds and metal in
medicine.
AUTHOR BIOGRAPHIES
Bo-Wei Huang received his B.S. and
M.S. degree in Chemistry from Tam-
kang University, Taiwan, in 2014 and
2016, respectively. He undertook
research on synthesis of the organo-
metallic manganese complexes under
the supervision of Professor Chung-
Hung Hsieh.
SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
How to cite this article: Huang B-W,
Minh-Trung Nguyen is currently a
Lecturer at Tay Nguyen University,
Vietnam. He received his M.S. degree
of Science in Chemical Biology, Tam-
kang University, Taiwan, under the
supervision of Professor Chung-Hung
Hsieh. His scientific interests include
Nguyen M-T, Hsieh C-H. Reaction of small
molecules O2, NO, CO, and the Naldini salt
(PPh3)2MnBr2: Characterized by infrared
spectroscopy, elemental analysis, and single-crystal
X-ray diffraction. J Chin Chem Soc. 2019;1–6.
https://doi.org/10.1002/jccs.201900463