Experimental and theoretical study of the substituted (η6-arene)Cr(CO)3 complexes

Article abstract of DOI:10.13005/ojc/330218

Synthesis of arenetricarbonylchromium(0) complexes, [(η⁶-arene)Cr(CO)₃], has been carried out, wherein arene were benzene (Ph), chlorobenzene (PhCl), phenyl trimethyl silane (PhSiMe₃), and acenaphthene (PhNp). Characterization of the compounds was carried out using NMR, IR and UV-visible spectrophotometers. Electronic absorption of these complexes were measured in various solvents namely methanol, methylene chloride, chloroform, benzene, and isooctane. The complexes showed the electronic absorption of the lowest in the energy range of 313-320 nm, with a relatively high intensity. Density functional theory at the B3LYP/LanL2DZ level of theory was also used to study the geometry parameters, binding energy (BE), vibrational spectra, electronic spectra, frontier molecular orbital (NBO analysis), charge transfer (CT) of the complexes. It was found that the order of the complex stability is: (PhSiMe₃)Cr(CO)₃> (Ph)Cr(CO)₃> (PhNp)Cr(CO)₃> (PhCl)Cr(CO)₃. The NBO analysis showed that the stability of the complexes arising from intramolecular interactions and electron delocalization in which synergistic interaction occurs in the arene hyper conjugative orbital ring for metal antibonding orbital and back donation (via metal bonding orbital to bond antibonding orbital ring). The electronic spectrum shows the charge transfer is dominated by ligand to metal charge transfer (LMCT) transition, except for (PhNpe) Cr(CO)₃ that is dominated by metal to ligand charge transfer (MLCT) and only a small portion is set to d-d transition.

Full text of DOI:10.13005/ojc/330218

ISSN: 0970-020 X
CODEN: OJCHEG
2017, Vol. 33, No. (2):
Pg. 717-724
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Experimental and Theoretical Study of the
6
Substituted (η -arene)Cr(CO)3 Complexes
AgUS AbHI PURwOkO* and SAPRIzAL HAdISAPUTRA
Chemistry Education Department, University of Mataram, Indonesia.
*Corresponding author E-mail: agus_ap@unram.ac.id
http://dx.doi.org/10.13005/ojc/330218
(Received: March 16, 2017; Accepted: April 14, 2017)
AbSTRACT
Synthesis of arenetricarbonylchromium(0) complexes, [(η6-arene)Cr(CO)3], has been carried
out, wherein arene were benzene (Ph), chlorobenzene (PhCl), phenyl trimethyl silane (PhSiMe3),
and acenaphthene (PhNp). Characterization of the compounds was carried out using NMR, IR and
UV-visible spectrophotometers.Electronic absorption of these complexes were measured in various
solvents namely methanol, methylene chloride, chloroform, benzene, and isooctane.The complexes
showed the electronic absorption of the lowest in the energy range of 313-320 nm, with a relatively
high intensity. Density functional theory at the B3LYP/LanL2DZ level of theory was also used to
study the geometry parameters, binding energy (BE), vibrational spectra, electronic spectra, frontier
molecular orbital (NBO analysis), charge transfer (CT) of the complexes. It was found that the order
of the complex stability is: (PhSiMe3)Cr(CO)3> (Ph)Cr(CO)3> (PhNp)Cr(CO)3> (PhCl)Cr(CO)3. The
NBO analysis showed that the stability of the complexes arising from intramolecular interactions and
electron delocalization in which synergistic interaction occurs in the arene hyper conjugative orbital
ring for metal antibonding orbital and back donation (via metal bonding orbital to bond antibonding
orbital ring). The electronic spectrum shows the charge transfer is dominated by ligand to metal
charge transfer (LMCT) transition, except for (PhNpe) Cr(CO)3that is dominated by metal to ligand
charge transfer (MLCT) and only a small portion is set to d-d transition.
keywords: Arenetricarbonylchromium, Charge transfer transition, DFT, TD-DFT, NBO.
INTROdUCTION
information storage devices and nonlinear optical
materials10-12. Many earlier studies have explored
preparation of arena chromium tricarbonyl
compounds, yet, their syntheses remain an ongoing
challenge. The presence of electron withdrawing
substituent on the benzene ring deflects p-electron
density of the arene, therefore the arene fails to react
Arene chromium tricarbonyl compounds
have been explored extensively and are very
versatile agents1-9. This compound has many
applications ranging from organic synthesis,
molecular switches, tunable molecular cables, optical

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PURwOkOB & HADISAPUTRA, Orient. J. Chem., Vol. 33(2), 717-724 (2017)
with the chromium hexacarbonyl;several arenes with Physical measurements
electron withdrawing substituentsdo not undergo
The infrared spectra were recorded on a
complexation, e.g. benzoic acid, benzaldehyde, Perkin-Elmer 283B spectrophotometer using kBr
nitrobenzene and benzonitrile13.
pellet. Electronic spectra were measured on UV-
Vis (HP 8450A) spectrophotometer in methanol,
The polysubstituted complex reported in benzene, chloroform, dichloromethane, and iso
this paper are (benzene)Cr(CO)3, (chlorobenzene) octane solution. 1H NMR spectra were obtained at
Cr(CO)3, (acenaphthene) Cr(CO)3, and room temperature in CDCl3 using a Bruker AM 360
(phenyltrimethylsilane)Cr(CO)3. Earlier study spectrometer.
explored the nature of the lowest excited states of
these complexes, in which it was reported that the Computational Method
lowest absorption energy band consist with a mixture
All calculations have been performed
of ligand field (LF) and metal to arene charge transfer with the GAUSSIAN-03 program15. Geometry
(MArCT) transitions14. Unfortunately, the definite optimizations utilized the B3LYP method16-18 and
order of these transitions could not be resolved well the LANL2DZ basis set19. Previous studies have
experimentally.This study reported the synthesis and shown this to be an appropriate level of theory
quantum chemical study of polysubstituted (η6-arene) for chromium tricarbonyl complex of arenes20-21
.
Cr(CO)3complexes. The quantum chemical study NBO22-24 calculations have been done at B3LYP/
includes geometry molecules, electronic populations LANL2DZ level.
and electronic structures of the complexes. The
theoretical analysis was performed for optimized
molecular geometry, frontier molecular orbital by
using the natural bond orbitals scheme, vibrational
RESULTS and dISCUSSION
The structures of arene chromium
frequencies, and electronic absorption spectra.The tricarbonyl complexes were optimized at the density
latterwasusedtoidentifythenatureoftheinteractions functional level of theory using the B3LYP/LanL2DZ
between metal and the ligands in terms of the methodology. The different types of substituents
intensity of metal to ligand or ligand to metal charge were added into the benzene unit as depicted in
transfer (MLCT/LLCT). The electronic absorption Scheme 1. Figure 1 depicts the mode of substitution
spectra were calculated by time dependent density of the benzene unit, which was performed with all of
functional theory (TD-DFT) to interpret the UV–Vis the aforementioned moieties.
spectra obtained at an experimental level.
Thegeometricalpropertiesofthecomplexes
ExPERIMENTAL
show that the structural changes in (η6-arene)Cr(CO)3
complex induced by introducing different substituent
All reagents were commercially available groups is very small (Fig. 1) owing to the tripod C-O
and were used without further purification.
bonds making the molecule rigid. This leads to a
small number of conformational isomers, and as
a result the computational effort is also reduced.
Synthesis
In general, the chromium tricarbonyl The calculated geometry is in a good agreement
complexes were synthesized by refluxing the same with the X-ray structural measurements of (Ph)
amount of moles of chromium hexacarbonyl and Cr(CO)3. The calculated Cr-O bond distances for all
appropriate aromatic ligands in aninert solvent complexes are relatively similar range from 1.8293
for 9 - 48 hours depending on the arene ligands. Å to 1.8386 Å. In the complex of (PhNp)Cr(CO)3 the
The mixtures were then filtered using alumina position of Cr(CO)3 tripod 0.17 Å shifts from the ring
column, followed by rotatory evaporation, and center toward the most external C-C bond (parallel
recrystallization.The complexes are obtained in the to the bond between the two rings). The distance of
form of robust solids which have the color ranging chromium to the ring center for (PhNp)Cr(CO)3 is
from yellow to orange. They are relatively stable in about 1.80 Å, a slightly longer distance compared
air at room temperature.
to benzene-Cr interaction at (Ph)Cr(CO)3 of 1.720 Å
(exp.: 1.724-1.726 Å)25.

PURwOkOB & HADISAPUTRA, Orient. J. Chem., Vol. 33(2), 717-724 (2017)
719
Hexacarbonylchromium(0), Cr(CO)6, is a
reactantinthesynthesisof(arene)Cr(CO)3complexes.
In the Cr(CO)6 molecule, Cr-C-O bond has a linear
shape and structure of the Cr-C-O can easily be
identified on the IR spectrum that showed CO
stretching mode in the 1850-2125 cm-1 26.The unique
identity of (arene)Cr(CO)3 is the presence of two
high-intensity IR absorption which are stretching
modes of COligand; the energy absorptions are in
the area 2000 - 1960 cm-1, and in the area of energy
from 1910 to 1870 cm-1. Assuming C3v symmetry
locally on the cluster of Cr(CO)3, the two uptakes
is thought to originate from vibrations of symmetric
non degenerate (A1) and antisymmetric double
(prior coordinated with the group Cr(CO)3. This
phenomenon is interpreted as a form of a reduction
in the degree of aromaticity of the ring of arene after
coordination with chromium group of tricarbonyl29;
an explanation that is consistent with the results of
1HNMR spectra in this study. Interaction of Cr(CO)3
with the arene ring reduce selectron density in the
ring30. This results in lower degrees of aromaticity,
manifested in the 1HNMR spectra that indicate the
presence of hydrogen aromatic shift into a higher
energy position (up field) (d = 4.6 to 5.6 ppm, while
the free aromatic ranging from 6.0 to 7.0 ppm).
A characteristic feature of electronic
absorptions of arenetricarbonylchromium(0)
complexes is the maximum absorption
in the region 313-320 nm with high intensity
(ε ~ 0.97 x 104 up to 2.04 x 104 M-1cm-1), except
for (PhNp)Cr(CO)3complex, that has lmax at 352
nm with an intensity that is almost the same
(ε ~ 0.91 x 104 M-1cm-1).Thisindicatesatransitionfrom
metal to ligand and ligand to metal charge transfers
(MLCT/LMCT).
1
degenerate (E) 27. IR spectra and HNMR spectra
for all of four chromium tricarbonyl complexes are
presented in Table 1.
X-ray crystallography and neutron
diffraction28 concluded that the C - C in the
arene ring elongated compared to its native form
R
In order to assign the already reported
experimental electronic absorption bands of (Ph)
Cr(CO)3, (PhCl)Cr(CO)3, (PhNp)Cr(CO)3, and
(PhSiMe)Cr(CO)3, the TD-DFT calculations have
been carried out on these complexes in methanol
at the B3LYP/GEN level of theory. TD-DFT is a
useful method for studying excitation energies, and
its application has increased in the recent years31.
C
C
CO
CO
CO
OC
OC
CO
Scheme 1: Molecular structure of the studied
polysubstituted (η6-arene)Cr(CO)3 complexes
(Ph)Cr(CO)3 (side)
(PhCl)Cr(CO)3 (side)
(PhNp)Cr(CO)3 (side)
(PhSiMe)Cr(CO)3 (side)
(Ph)Cr(CO)3
(PhCl)Cr(CO)3
(PhNp)Cr(CO)3
(PhSiMe)Cr(CO)3
Fig. 1:Two projections of the fully optimized structures of (η6-arene)-Cr(CO)3
complexes at b3LYP level of theory

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PURwOkOB & HADISAPUTRA, Orient. J. Chem., Vol. 33(2), 717-724 (2017)
This method does give some errors in the excitation and transitions with significant coefficients of the
energies of charge-transfer states, however; better wave function are listed in Table 4, along with the
results may be obtained by using hybrid functionals experimental transition wavelengths (lexp).
which include a mixture of exact Hartree-Fock
exchange with DFT exchange correlation32. The
Transition metal complexes generally
calculated electronic excitation energies and show three types of electronic excitation bands that
transition wavelengths (lcal) of the complexes, cover a wide wavelength range: d-d (crystal-field)
along with their oscillator strengths, assignments transitions (300 - 1500 nm); metal-to-ligand charge-
transfer (MLCT) and ligand-to-metal charge transfer
(LMCT) transitions (200 - 500 nm); transitions that
Table 1: geometric parameters of the fully
optimized structures of (η6-arene)Cr(CO)3
complexes at b3LYP level of theory
are localized on the ligands commonly known as
intra-ligand charge transfer (ILCT) transitions, that
regularly occur in the ultraviolet region33.ILCT results
from n → p* and n → p* transitions and are affected
by the type of coordination.
geometrical Complexes
Parameters
bond
(Ph)
(PhCl) (PhNp) (PhSiMe3)
The scaling factor 0.72 was used to correct
the calculated singlet-singlet electronic excitation
wavelengths34. The calculate electronic spectrum
of (Ph)Cr(CO)3, (PhCl)Cr(CO)3, and (PhSiMe3)
Cr(CO)3 have closely similar bands, between 325-
360 nm, that can be attributed mainly to ligand to
metal charge transfer transitions and smaller band
with low oscillator strength (f < 0.0005), that is due
to a d-d transition. The latter assignment was made
since d-d transitions usually have very low intensities
and lack of solvent dependent. For ((PhNp))Cr(CO)3
complex, the band at 426 nm with oscillator strength
Length (A) Cr(CO)3 Cr(CO)3 Cr(CO)3 Cr(CO)3
Cr-O12(10) 1.8333 1.8386 1.8265 1.8281
Cr-O13(11) 1.8354 1.8354 1.8314 1.8293
Cr-O14(12) 1.8386 1.8339 1.8203 1.8304
Cr-C1
Cr-C2
Cr-C3
Cr-C4
Cr-C5
Cr-C6
2.3183 2.3183
2.353 2.3015
2.3172 2.3172 2.4035 2.3469
2.3281 2.3281 2.4586 2.3027
2.2985 2.2985 2.3266 2.326
2.3124 2.3124 2.2842 2.3188
2.298
2.298
2.3269 2.3243
Table 2: Experimented and calculated 1H NMR and
IR spectra of the (η6-arene)Cr(CO)3complexes
Complexes
1H-NMR, d (ppm)a
IR, CO, cm-1 (lit)b
H aromatic H substituent
A1
E
1887 (1898) (1878)f
1922 (1931)e(1981)f
1871 (1868)f
(Ph)Cr(CO)3
5,4 (s)
"-"
"-"
1965 (1974)d(1939)f
1980 (1992)e(1947)f
1968 (1928)f
(PhCl)Cr(CO)3
(PhNp)Cr(CO)3
5,4 – 5,5 (m)
7,3 – 7,7 (m)
3,4 (s)
0,3 (s)
(PhSiMe)Cr(CO)3 5,2 – 5,6 (m)
1980 (1934)f
1904 (1875)
a) The spectra were taken in CDCl3 solution; using TMS as an internal
standard; (s) = singlet, (m) = multiplet
b) Stretching frequencies of CO relative to polystyrene. Using solvents CDCl3
d) In CHCl330
e) In cyclohexane 30
f) Calculated IR spectra

PURwOkOB & HADISAPUTRA, Orient. J. Chem., Vol. 33(2), 717-724 (2017)
721
of 0.0240, is the most intense and attributed to
electronic excitation from HOMO-2 to LUMO. This
band, therefore, arises from a mixed of MLCT and
LMCT charge transfer character.
their monomer. The calculated binding energies for
the complexes are listed in Table 5.
The calculated binding energy of the
complex are 48.73 kcal.mol-1, 45.64 kcal.mol-1,
45.62 kcal.mol-1, and 41.46 kcal.mol-1 for (PhSiMe3)
Cr(CO)3, (Ph)Cr(CO)3, (PhNp)Cr(CO)3, (PhCl)
Cr(CO)3, respectively. The (Ph)Cr(CO)3 binding
energy is 45.64 kcal.mol-1, not too far from the
In general, the binding energy is related to
the stability of the complexes.The binding energies
for the chromium-arene complexes were calculated
as the energy difference between the complexes and
Table 3: Electronic absorbtion data of (η6-arene)Cr(CO)3complexes
in a variety of solvent-saturated N2 at 298 k
Complexes
Absorbance maximum (λmax, nm)
CH3OH
CH2Cl2
CHCl3
C6H6
C8H18
(Ph)Cr(CO)3
312
320
344
315
313
319
347
316
315
320
350
318
313
320
352
316
313
318
353
316
(PhCl)Cr(CO)3
(PhNp)Cr(CO)3
(PhSiMe3)Cr(CO)3
Table 4: Caculation of electronic absorptions of (Ph)Cr(CO)3, (PhCl)Cr(CO)3, (PhNp)Cr(CO)3, and
(PhSiMe3)Cr(CO)3complexes, in methanol, from Td-dFT calculations at the b3LYP/LanL2dz.
Complexes
(Ph)Cr(CO)3
(PhCl)Cr(CO)3
Electronic Transition weight % Oscillator Excitation
scaled
transition Coefficient
(c)
of
Strength
Energy
lcal
lcal
lexp
Assignment
Transition
H →L
0.471
0.387
22.2
0.0001
0.0007
3.288
3.363
377
368
271
265
MCT/ILCT
d-d/MLCT/LMCT
/LLCT/ILCT
LMCT/ILCT
LMCT/ILCT
LMCT/ILCT
d-d/MLCT/LMCT
/LLCT/ILCT
d-d/MLCT/LMCT
/LLCT/ILCT
LMCT/ILCT
MLCT /LMCT
/ILCT
H → L+3
15.01
H → L+3
H → L
0.185
-0.23
3.42
5.09
0.0051
0.0002
0.0043
0.0000
3.446
3.227
3.290
359
384
360
259
276
259
312
320
H-2→ L+2
H-1→ L
0.384
-0.240
14.75
5.53
H-1→ L
0.374
13.97
0.0009
3.688
336
242
(PhNp)Cr(CO)3
H→ L
0.617
0.559
38.02
31.27
0.0056
0.0240
2.736
2.906
453
426
326
307
H-2→ L
344
315
H → L+2
0.474
0.421
0.591
0.273
22.50
17.74
34.90
7.44
0.0074
0.0001
0.0030
0.0000
3.390
3.297
3.632
365
376
341
263
270
245
LMCT/ILCT
LMCT/ILCT
LMCT/ILCT
d-d/MLCT/LMCT
/LLCT/ILCT
LMCT/ILCT
(PhSiMe3)Cr(CO)3 H-1 → L+2
H-1 → L+1
H-2 → L+2
H → L
0.288
8.29
0.0002
3.809
325
234

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PURwOkOB & HADISAPUTRA, Orient. J. Chem., Vol. 33(2), 717-724 (2017)
Table 5: Calculated binding energy (bE), selected second order binding energy (E2), frontier
molecular orbital (HOMO-LUMO), and charge transfer (CT) of (η6-arene)Cr(CO)3complexes.
E2 (kcal)
Cr-CO Cr-O
EHOMO
(a.u)
ELUMO
(a.u)
Mulliken CT
(Ring Cr)
Systems
bE (kcal.mol-1) Ring
→
→
Ring
→
(Ph)Cr(CO)3
(PhCl)Cr(CO)3
(PhNp)Cr(CO)3
-45.64 (43)*
-41.46
199.48
199.28
151.35
202.33
15.64
15.36
16.66
16.72
-0.2213
-0.2109
-0.2284
-0.2175
-0.0584
-0.0773
-0.0687
-0.0562
0.167
0.133
0.135
0.195
-45.62
(PhSiMe3)Cr(CO)3 -48.72
*Experimental value 35
.
experimental value (43 kcal.mol-1) as reported by
Brown et al.. The binding energy trend shows that
electron withdrawing substituent on the ring reduces
the binding energies from the initial (Ph)Cr(CO)3. In
contrast, the presence of additional two benzene
rings on (PhNp)Cr(CO)3acts as electron donating
groups, and therefore the binding energy increase
compared to (Ph)Cr(CO)3 binding energy. The
binding energy trend is consistent with calculated
Mulliken charge transfer trend from ring → Cr.
CONCLUSION
The aim of this study was to synthesize
tricarbonylchromium(0) arene complexes and to
analyze synthesis products using experimental
and theory studies. Synthesis products of
tricarbonylchromium (0) arene complexes were
(Ph)Cr(CO)3, (PhCl)Cr(CO)3, (PhSiMe3)Cr(CO)3,
1
and (PhNp)Cr(CO)3. Characterization by H-NMR,
IR, and UV-visible show that the complexes were
successfully synthesized. DFT study at B3LYP/
LanL2DZ level of theory was also used to study
the geometry parameters, binding energy (BE), the
frontier molecular orbital (NBO analysis), the charge
transfer (CT), electronic and vibration spectrum.
The electronic spectrum shows the transfer fee is
dominated by metal to ligand charge transfer (LMCT)
transition, except (PhNp)Cr(CO)3 is dominated by
metal to ligand charge transfer (MLCT) and only a
small portion is set to d-d transition.It was found that
the complex stability order were (PhSiMe3)Cr(CO)3>
(Ph)Cr(CO)3> (PhNp)Cr(CO)3> (PhCl)Cr(CO)3.NBO
analysis showed that the stability of the complexes
arising from hyperconjugative orbital rings for metal
antibonding orbital donation and back bonding
orbital.
The stability trend of the complexes is
further studied by the second-order binding energies
(E2) trend based on the natural bond orbital (NBO)
analysis.E2 corresponds to the intensity of interaction
between Lewis donor and non-Lewis acceptor
NBO30-32, 36,37. Table 5 shows a positive correlation
of the binding energy with the second-order binding
energy. All the complexes have either the bonding
(ring ’! s*Cr–CO) (or) back bonding (Cr–CO → ring)
interactions.The maximum E2 contribution of ring →
s*Cr–CO for(PhSiMe3)Cr(CO)3, (Ph)Cr(CO)3, (PhCl)
Cr(CO)3range from 199.28-202.33 kcal with Cr–CO
→ ringback bonding15.64-16.72 kcal.The difference
was found for ring → s*Cr–COE2 maximum of
(PhNp)Cr(CO)3 complex (151.35 kcal), where two
additional benzene on ligand (acenapthene) may
distort interaction between Lewis donor and non-
Lewis acceptor NBO.
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