The rotation of the nitro and formyl groups relative to the aromatic ring in some ortho-nitroarylaldehydes

Article abstract of DOI:10.3184/030823408X338738

X-Ray crystallographic studies have shown that in ortho-nitroarylaldehydes the plane of an aryl nitro group is rotated relative to the aromatic ring to a greater extent than that of the adjacent formyl group.

Full text of DOI:10.3184/030823408X338738

476 RESEARCH PAPER
AUGUST, 476–478
JOURNAL OF CHEMICAL RESEARCH 2008
The rotation of the nitro and formyl groups relative to the aromatic ring
in some ortho-nitroarylaldehydes
James R. Hanson,* Peter B. Hitchcock and Francois Toche
Department of Chemistry, University of Sussex, Brighton, Sussex BN1 9QJ, UK
X-Ray crystallographic studies have shown that in ortho-nitroarylaldehydes the plane of an aryl nitro group is
rotated relative to the aromatic ring to a greater extent than that of the adjacent formyl group.
Keywords steric hindrance, conformation, o-nitroaldehydes
The steric interactions of a nitro group with an adjacent
substituent on an aromatic ring may be relieved by its rotation
out of the plane of the aromatic ring. There is a balance
between the consequent loss of resonance energy and the relief
of this steric compression.1 This rotation has an impact on the
chemistry of the ortho substituted aromatic nitro compounds
in diminishing the rate of aromatic nucleophilic substitution
of para bromo substituents2 and the activation of aryl methyl
groups by nitro groups in carbanion condensation reactions.3
X-Ray crystallographic studies have shown4 that one ortho
substituent can produce a rotation between the plane of the nitro
group and the aromatic ring of approximately 40° whilst two
ortho substituents lead to a rotation of about 70°. The extent of
this rotation of the plane of the nitro group may be diminished
by an electron-donating para methoxyl group.5 When the nitro
group is adjacent to a carbonyl group there is the possibility of
interaction between the two dipoles which may affect the plane
of rotation. In this paper, we compare by X-ray crystallography,
WKHꢀLQÀXHQFHꢀRIꢀVXEVWLWXHQWVꢀRQꢀWKHꢀURWDWLRQꢀRIꢀDGMDFHQWꢀQLWURꢀ
and carbonyl groups in the solid state.
Fig.
1
X-Ray crystal structure of 4-bromo-2-formylnitro-
benzene; interplanar angles: nitro:aryl, 25.8°; formyl:aryl, 32.6°.
4-Bromo-2-formylnitrobenzene (5-bromo-2-nitrobenzalde-
hyde), prepared by the nitration of 3-bromobenzaldehyde,6
gave suitable crystals for X-ray crystallography (see Fig. 1).
The mutual interaction of the aldehyde and nitro groups led
to their rotation relative to the plane of the aromatic ring to
WKHꢀH[WHQWꢀRIꢀꢁꢂꢃꢄꢀƒꢀDQGꢀꢂꢅꢃꢆꢀƒꢀUHVSHFWLYHO\ꢃꢀ7KHꢀLQÀXHQFHꢀRIꢀDꢀ
para oxygen substituent on the rotation of the formyl and nitro
groups was then examined. Unfortunately 4,5-dimethoxy-
2-nitrobenzaldehyde, prepared by nitrating veratraldehyde,
FU\VWDOOLVHGꢀIURPꢀDꢀQXPEHUꢀRIꢀGLIIHUHQWꢀVROYHQWVꢀDVꢀYHU\ꢀ¿QHꢀ
needles that were unsuitable for X-ray crystallography. 4,5-
Methylenedioxy-2-nitrobenzaldehyde, prepared by nitrating
piperonal,7 gave better crystals. Although the methylenedioxy
group has a diminished electron-donating effect compared
to the methoxy group,8 the X-ray crystal structure of 4,5-
methylenedioxy-2-nitrobenzaldehyde (Fig. 2) showed that the
planes of rotation of the formyl and nitro groups were slightly
diminished to 22.9° and 24.2°.
Fig.
2
X-Ray crystal structure of 4,5-methylenedioxy-2-
nitrobenzaldehyde; interplanar angles: nitro:aryl, 24.2°; formyl:
aryl, 22.9°.
A difference between the rotation of the nitro group and the
formyl group was observed in a comparison of the structures of
4-hydroxy-3-methoxy-2-nitrobenzaldehyde (2-nitrovanillin,
Fig. 3), 4-acetoxy-3,5-dimethoxy-2-nitrobenzaldehyde (Fig. 4)
and 5-bromo-2,3-dimethoxy-6-nitrobenzaldehyde (Fig. 5).
7KHVHꢀ FRPSRXQGVꢀ ZHUHꢀ FKRVHQꢀ WRꢀ UHÀHFWꢀ WKHꢀ HIIHFWꢀ RIꢀ
substituents adjacent to and para to the nitro and formyl
groups. 2-Nitrovanillin was obtained by nitrating 4-
acetoxyvanillin and hydrolysing the acetate.9 4-Acetoxy-3,5-
dimethoxy-2-nitrobenzaldehyde was obtained by nitrating
the acetate of syringaldehyde.10 The nitration of 3,4,5-
trimethoxybenzaldehyde gave 3,4,5-trimethoxynitrobenzene
as a consequence of ipso substitution of the formyl group.
5-Bromo-2,3-dimethoxy-6-nitrobenzaldehyde was prepared
by brominating o-vanillin, methylating the phenol and
Fig. 3 X-Ray crystal structure of 4-hydroxy-3-methoxy-2-
nitrobenzaldehyde; interplanar angles: nitro:aryl, 61.8°; formyl:
aryl, 1.7°.
* Correspondent. E-mail: j.r.hanson@scilet.com

JOURNAL OF CHEMICAL RESEARCH 2008 477
determined as nujol mulls. Mass spectra were determined on a Bruker
Daltonics Apex III electrospray mass spectrometer. The following
ortho-nitrobenzaldehydes were prepared by literature methods. 4-
Bromo-2-formylnitrobenzene had m.p. 71°C (lit.,6 69.1–70.8°C);
4,5-methylenedioxy-2-nitrobenzaldehyde had m.p. 97°C (lit.,7
98.5°C); 4-hydroxy-3-methoxy-2-nitrobenzaldehyde had m.p. 136°C
(lit.,9 137°C); 5-bromo-2,3-dimethoxy-6-nitrobenzaldehyde had m.p.
141°C (lit.,11 141°C).
Nitration of 3,4,5-trimethoxybenzaldehyde: A nitrating mixture
of conc. nitric acid (6 cm3) and conc. sulfuric acid (12 cm3) was
prepared and cooled in an ice-bath. 3,4,5-Trimethoxybenzaldehyde
(2 g) was added in portions over a period of 10 min and the mixture
was left at room temperature for 45 min. It was poured into ice-
ZDWHUꢀDQGꢀWKHꢀSURGXFWꢀZDVꢀ¿OWHUHGꢀDQGꢀUHFU\VWDOOLVHGꢀIURPꢀDTXHRXVꢀ
methanol to give 3,4,5-trimethoxynitrobenzene (0.7 g) as needles,
m.p. 98°C (lit.,12 99°CꢇꢈꢀȞmax/cm-1ꢀꢉꢄꢉꢊꢈꢀꢉꢅꢂꢁꢈꢀꢉꢋꢊꢌꢈꢀꢉꢁꢁꢆꢍꢀįH 3.95
(9H, 3ꢀuꢀOMe), 7.50 (2H, s, ArH).
Nitration of 4-acetoxy-3,5-dimethoxybenzaldehyde: A nitrating
mixture comprising conc. nitric acid (8 cm3), glacial acetic acid
(5 cm3) and acetic anhydride (5 cm3) was carefully prepared with ice-
cooling behind a screen.
Fig. 4 X-Ray crystal structure of 4-acetoxy-3,5-dimethoxy-
2-nitrobenzaldehyde; interplanar angles: nitro:aryl, 89.3°;
formyl:aryl, 4.7°.
CAUTION: Mixtures of fuming nitric acid and acetic
anhydride are known to be dangerously unstable and can
detonate.13–15 Although in the present case the acid used is
not fuming, caution is advised.
4-Acetoxy-3,5-dimethoxybenzaldehyde10 (1.5 g) in glacial acetic acid
(10 cm3) was added and the mixture was left in ice for 1 h. It was poured
onto ice to give 4-acetoxy-3,5-dimethoxy-2-nitrobenzaldehyde (1.2 g)
which crystallised from aqueous methanol as needles, m.p.112°C,
Ȟmax/cm-1ꢀꢉꢌꢌꢌꢈꢀꢉꢌꢎꢉꢈꢀꢉꢅꢆꢋꢈꢀꢉꢅꢁꢉꢈꢉꢁꢁꢄꢍꢀįH 2.39 (3H, s, OAc), 3.95
(6H, s, 2ꢀ uꢀ OMe), 7.26 (1H, s, ArH), 9.93 (1H, s, CHO); HRMS
Found (in MeOH) M+ 324.0682 C12H15NO8Na requires 324.0689;
Found (in MeCN) M+ 292.0419 C11H11NO7Na requires 292.0428.
We thank Dr. Ali Al-Sada for these measurements.
X-Ray crystal data and structure determinations
Data were collected using
a
Kappa CCD diffractometer.
No absorption corrections were applied. Structures were solved by
GLUHFWꢀPHWKRGVꢀDQGꢀUH¿QHGꢀXVLQJꢀ6+(/;/ꢏꢊꢌꢃꢀ7KHꢀGUDZLQJVꢀXVHGꢀ
ORTEP-3 for Windows. The CCDC Numbers given below contain
the supplementary crystallographic data for this paper. The data can
be obtained free of charge from the Cambridge Crystallographic
Centre via www.ccdc.cam.ac.uk/data_request.cif.
Fig. 5 X-Ray crystal structure of 5-bromo-2,3-dimethoxy-
6-nitrobenzaldehyde; interplanar angles: nitro:aryl, 85.2°;
formyl:aryl, 7.6°.
nitration.11 In all cases, the plane of the nitro group was rotated
VLJQL¿FDQWO\ꢀZLWKꢀUHVSHFWꢀWRꢀWKHꢀDURPDWLFꢀULQJꢀꢐꢂꢏQLWURYDQLOOLQꢈꢀ
61.8°, 4-acetoxy-3,5-dimethoxy-2-nitrobenzaldehyde, 89.3°,
5-bromo-2,3-dimethoxy-6-nitrobenzaldehyde, 85.2°) whilst
the formyl group remained essentially co-planar with the
aromatic ring (2-nitrovanillin, 1.7°, 4-acetoxy-3,5-dimethoxy-
2-nitrobenzaldehyde, 4.7°, 5-bromo-2,3-dimethoxy-6-nitro-
benzaldehyde, 7.6°).
Although these results were obtained in the crystalline state
and may therefore be affected by crystal packing effects,
they, nevertheless, show that the formyl group has far less of
a tendency to rotate than the nitro group. This suggests that
the electronic interactions between a formyl group and the
aromatic ring may be stronger than those of a nitro group.
In the course of characterisation of 4-acetoxy-3,5-
dimethoxy-2-nitrobenzaldehyde, the high-resolution mass
spectrum was obtained by electrospray ionisation at room
temperature. When this was carried out using methanol as a
solvent, the molecular ion that was observed, was that of a
methoxy hemi-acetal. The same effect was observed from the
parent 4-acetoxy-3,4-dimethoxybenzaldehyde. The molecular
ion of the aldehyde was observed using acetonitrile as the
solvent. Since methanol is a common solvent for electrospray
ionisation, this facile hemi-acetal formation from an aldehyde
might be misleading.
4-bromo-2-formylnitrobenzene
(5-bromo-2-nitrobenzaldehyde),
C7H4BrNO3: Mr 230.02, monoclinic, space group P2i/c (No 14),
aꢀ ꢀꢌꢃꢋꢊꢁꢉꢐꢋꢇꢈꢀbꢀ ꢀꢁꢃꢆꢌꢅꢎꢐꢂꢇꢈꢀcꢀ ꢀꢂꢄꢃꢊꢁꢉꢁꢐꢉꢅꢇꢀcꢈꢀĮꢀ ꢀȖꢀ ꢀꢊꢎꢀƒꢈꢀȕꢀ ꢀ
95.952(3)°, Vꢀ ꢀꢌꢌꢌꢃꢄꢌꢐꢌꢇꢀc3, Zꢀ ꢀꢋꢈꢀDcalcꢀ ꢀꢉꢃꢊꢄꢀJꢀFP-3ꢈꢀȝꢀ ꢀꢅꢃꢂꢅꢀPP-1,
F(OOO) 448. Crystal size 0.4ꢀ uꢀ 0.2ꢀ uꢀ 0.2 mm. A total of 3650
UHÀHFWLRQVꢀZHUHꢀFROOHFWHGꢀIRUꢀꢁꢃꢆꢌꢀꢑꢀșꢀꢑꢀꢂꢅꢃꢎꢎꢀƒꢀDQGꢀ±ꢆꢀ”ꢀhꢀ”ꢀꢆꢈꢀ±ꢋꢀ”ꢀk
”ꢀꢋꢈꢀ±ꢂꢊꢀ”ꢀlꢀ”ꢀꢁꢂꢃꢀ7KHUHꢀZHUHꢀꢉꢁꢅꢊꢀLQGHSHQGHQWꢀUHÀHFWLRQVꢀDQGꢀꢉꢉꢊꢌꢀ
UHÀHFWLRQVꢀZLWKꢀIꢀ!ꢀꢂıꢐIꢇꢀZHUHꢀXVHGꢀLQꢀWKHꢀUH¿QHPHQWꢃꢀ7KHꢀ¿QDOꢀ5ꢀ
indices were [Iꢀ!ꢀꢂıꢐI)] R1 0.033, wR2 0.069 and (all data) R1 0.040,
wR2ꢀꢎꢃꢎꢌꢉꢃꢀ7KHꢀODUJHVWꢀGLIIHUHQFHꢀSHDNꢀDQGꢀKROHꢀZHUHꢀꢎꢃꢄꢎꢀHc3 and
±ꢎꢃꢅꢆꢀHc3. CCDC No. 267843.
4,5-methylenedioxy-2-nitrobenzaldehyde, C8H5NO5: Mr 195.13,
orthorhombic, space group Pna21 (No 33), aꢀ ꢀ ꢉꢋꢃꢎꢉꢌꢐꢂꢇꢈꢀ
bꢀ ꢀꢁꢃꢌꢄꢆꢆꢐꢄꢇꢈꢀcꢀ ꢀꢉꢋꢃꢄꢎꢋꢌꢐꢉꢄꢇꢀcꢈꢀĮꢀ ꢀȕꢀ ꢀȖꢀ ꢀꢊꢎꢀƒꢈꢀVꢀ ꢀꢌꢌꢉꢃꢅꢐꢂꢇꢀc3,
Zꢀ ꢀꢋꢈꢀDcalcꢀ ꢀꢉꢃꢄꢆꢀJꢀFP-3ꢈꢀȝꢀ ꢀꢎꢃꢉꢋꢀPP-1, F(OOO) 408. Crystal size
0.1ꢀuꢀ0.1ꢀuꢀꢎꢃꢉꢀPPꢃꢀ$ꢀWRWDOꢀRIꢀꢁꢁꢅꢉꢀUHÀHFWLRQVꢀZHUHꢀFROOHFWHGꢀIRUꢀꢋꢃꢎꢁꢀ
ꢑꢀșꢀꢑꢀꢂꢄꢃꢉꢁꢀƒꢀDQGꢀ±ꢉꢅꢀ”ꢀhꢀ”ꢀꢉꢌꢈꢀ±ꢋꢀ”ꢀkꢀ”ꢀꢋꢈꢀ±ꢉꢌꢀ”ꢀlꢀ”ꢀꢉꢆꢃꢀ7KHUHꢀZHUHꢀ
ꢉꢋꢁꢎꢀLQGHSHQGHQWꢀUHÀHFWLRQVꢀDQGꢀꢉꢎꢎꢂꢀUHÀHFWLRQVꢀZLWKꢀIꢀ!ꢀꢂıꢐI) were
XVHGꢀLQꢀWKHꢀUH¿QHPHQWꢃꢀ7KHꢀ¿QDOꢀ5ꢀLQGLFHVꢀZHUHꢀ>Iꢀ!ꢀꢂıꢐI)] R1 0.050,
wR2 0.103 and (all data) R1 0.082, wR2 0.119. The largest difference
SHDNꢀDQGꢀKROHꢀZHUHꢀꢎꢃꢂꢅꢀHc3 DQGꢀ±ꢎꢃꢂꢁꢀHc3. CCDC No. 267844.
4-hydroxy-3-methoxy-2-nitrobenzaldehyde, C8H7NO5: Mr 197.15,
orthorhombic, space group P212121 (No 19), aꢀ ꢀ ꢁꢃꢆꢁꢆꢆꢐꢂꢇꢈꢀ
bꢀ ꢀꢉꢋꢃꢋꢂꢋꢌꢐꢅꢇꢈꢀcꢀ ꢀꢉꢅꢃꢂꢋꢁꢂꢐꢆꢇꢀcꢈꢀĮꢀ ꢀȕꢀ ꢀȖꢀ ꢀꢊꢎꢀƒꢈꢀVꢀ ꢀꢆꢋꢋꢃꢎꢌꢐꢌꢇꢀ
c3, Zꢀ ꢀꢋꢈꢀDcalcꢀ ꢀꢉꢃꢅꢅꢀJꢀFP-3ꢈꢀȝꢀ ꢀꢎꢃꢉꢁꢀPP-1, F(OOO) 408. Crystal
size 0.2ꢀuꢀ0.2ꢀuꢀꢎꢃꢉꢀPPꢃꢀ$ꢀWRWDOꢀRIꢀꢉꢎꢊꢄꢎꢀUHÀHFWLRQVꢀZHUHꢀFROOHFWHGꢀ
IRUꢀꢁꢃꢆꢊꢀꢑꢀșꢀꢑꢀꢂꢄꢃꢎꢎꢀƒꢀDQGꢀ±ꢋꢀ”ꢀhꢀ”ꢀꢋꢈꢀ±ꢉꢌꢀ”ꢀkꢀ”ꢀꢉꢌꢈꢀ±ꢉꢆꢀ”ꢀlꢀ”ꢀꢉꢆꢃꢀ
7KHUHꢀZHUHꢀꢉꢄꢄꢂꢀLQGHSHQGHQWꢀUHÀHFWLRQVꢀDQGꢀꢉꢋꢂꢊꢀUHÀHFWLRQVꢀZLWKꢀ
Iꢀ !ꢀ ꢂıꢐLꢇꢀ ZHUHꢀ XVHGꢀ LQꢀ WKHꢀ UH¿QHPHQWꢃꢀ 7KHꢀ ¿QDOꢀ 5ꢀ LQGLFHVꢀ ZHUHꢀ
[Iꢀ!ꢀꢂıꢐLꢇ@ꢀ51 0.036, wR2 0.091 and (all data) R1 0.044, wR2 0.096.
7KHꢀODUJHVWꢀGLIIHUHQFHꢀSHDNꢀDQGꢀKROHꢀZHUHꢀꢎꢃꢉꢊꢀHc3 DQGꢀꢏꢎꢃꢉꢊꢀHc3.
CCDC No. 267849.
Experimental
General experimental details: 1H NMR spectra were determined
4-acetoxy-3,5-dimethoxy-2-nitrobenzaldehyde, C11H11NO7: Mr
269.21, monoclinic, space group P2i/c (No 14), aꢀ ꢀ ꢉꢉꢃꢌꢊꢌꢋꢐꢉꢂꢇꢈꢀ
at 300 MHz for solutions in deuteriochloroform. IR spectra were

478 JOURNAL OF CHEMICAL RESEARCH 2008
bꢀ ꢀꢊꢃꢄꢎꢂꢂꢐꢄꢇꢈꢀcꢀ ꢀꢉꢉꢃꢎꢂꢁꢋꢐꢉꢂꢇꢀcꢈꢀĮꢀ ꢀȖꢀ ꢀꢊꢎꢀƒꢈꢀȕꢀ ꢀꢉꢎꢉꢃꢆꢆꢂꢐꢁꢇꢀƒꢈꢀ
Vꢀ ꢀꢉꢂꢂꢂꢃꢎꢐꢂꢇꢀc3, Zꢀ ꢀꢋꢈꢀ'calcꢀ ꢀꢉꢃꢋꢄꢀJꢀFP-3ꢈꢀȝꢀ ꢀꢎꢃꢉꢁꢀPP-1, F(OOO)
560. Crystal size 0.40ꢀuꢀ0.25ꢀuꢀꢎꢃꢎꢉꢀPPꢃꢀ$ꢀWRWDOꢀRIꢀꢅꢌꢊꢊꢀUHÀHFWLRQVꢀ
were collected for 3.53 < hꢀꢑꢂꢄꢃꢎꢁꢀƒꢀDQGꢀ±ꢉꢋꢀ”ꢀhꢀ”ꢀꢉꢁꢈꢀ±ꢉꢉꢀ”ꢀkꢀ”ꢀꢆꢈꢀ±ꢉꢁꢀ
”ꢀlꢀ”ꢀꢊꢃꢀ7KHUHꢀZHUHꢀꢂꢁꢌꢅꢀLQGHSHQGHQWꢀUHÀHFWLRQVꢀDQGꢀꢉꢌꢄꢋꢀUHÀHFWLRQVꢀ
with Iꢀ!ꢀꢂıꢐIꢇꢀZHUHꢀXVHGꢀLQꢀWKHꢀUH¿QHPHQWꢃꢀ7KHꢀ¿QDOꢀ5ꢀLQGLFHVꢀZHUHꢀ
[Iꢀ!ꢀꢂıꢐI)] R1 0.049, wR2 0.110 and (all data) R1 0.075, wR2 0.122.
7KHꢀODUJHVWꢀGLIIHUHQFHꢀSHDNꢀDQGꢀKROHꢀZHUHꢀꢎꢃꢁꢅꢀHc3 DQGꢀ±ꢎꢃꢂꢌꢀHc3.
CCDC No. 267850.
5-bromo-2,3-dimethoxy-6-nitrobenzaldehyde, C9H8BrNO5: Mr
290.07, monoclinic, space group P2i/c (No 14), aꢀ ꢀ ꢉꢁꢃꢎꢄꢋꢊꢐꢌꢇꢈꢀ
bꢀ ꢀ ꢉꢎꢃꢎꢅꢄꢎꢐꢅꢇꢈꢀ cꢀ ꢀ ꢆꢃꢎꢊꢊꢁꢐꢋꢇꢀ cꢈꢀ Įꢀ ꢀ Ȗꢀ ꢀ ꢊꢎꢀƒꢈꢀ ȕꢀ ꢀ ꢉꢎꢎꢃꢉꢅꢆꢐꢁꢇꢀƒꢈꢀ
Vꢀ ꢀꢉꢎꢋꢌꢃꢋꢉꢐꢊꢇꢀc3, Zꢀ ꢀꢋꢈꢀDcalcꢀ ꢀꢉꢃꢆꢋꢀJꢀFP-3ꢈꢀȝꢀ ꢀꢁꢃꢉꢁꢀPP-1, F(OOO)
576. Crystal size 0.25ꢀuꢀ0.08ꢀuꢀꢎꢃꢎꢅꢀPPꢃꢀ$ꢀWRWDOꢀRIꢀꢉꢋꢁꢌꢉꢀUHÀHFWLRQVꢀ
were collected for 3.42 < hꢀꢑꢀꢂꢄꢃꢎꢁꢀƒꢀDQGꢀ±ꢉꢄꢀ”ꢀhꢀ”ꢀꢉꢄꢈꢀ±ꢉꢂꢀ”ꢀkꢀ”ꢀ
ꢉꢂꢈꢀ±ꢉꢎꢀ”ꢀlꢀ”ꢀꢊꢃꢀ7KHUHꢀZHUHꢀꢂꢎꢆꢌꢀLQGHSHQGHQWꢀUHÀHFWLRQVꢀDQGꢀꢉꢄꢌꢅꢀ
UHÀHFWLRQVꢀZLWKꢀIꢀ!ꢀꢂıꢐIꢇꢀZHUHꢀXVHGꢀLQꢀWKHꢀUH¿QHPHQWꢃꢀ7KHꢀ¿QDOꢀ5ꢀ
indices were [Iꢀ!ꢀꢂıꢐI)] R1 0.030, wR2 0.059 and (all data) R1 0.043,
wR2ꢀꢎꢃꢎꢄꢁꢃꢀ7KHꢀODUJHVWꢀGLIIHUHQFHꢀSHDNꢀDQGꢀKROHꢀZHUHꢀꢎꢃꢁꢂꢀHc3 and
±ꢎꢃꢁꢂꢀHc3. CCDC No. 276702.
Received 4 April 2008; accepted 21 June 2008
Paper 08/5187 doi: 10.3184/030823408X338738
Published online: 21 August 2008
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