Asian Journal of Chemistry; Vol. 25, No. 9 (2013), 5115-5116
NOTE
Synthesis and Supramolecular Structure of 2-Acetyl-1-naphthol
1,*
2
2
2
2
1,*
QIONG SU , XIN-YING ZHANG , YU-JIE ZHANG , LI ZHAO , LI WANG and YAN-BIN WANG
1
School of Chemical Engineering, Northwest University of nationalities, Lanzhou 730030, P.R. China
School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P.R. China
2
*
Corresponding author: E-mail: ybwang@126.com
Received: 16 July 2012;
(
Accepted: 25 March 2013)
AJC-13154
2
-Acetyl-1-naphthol with the molecular formula C12
H
10
2
O , is stabilized by intramolecular O2-H2···O1 hydrogen bond forming a
six-membered ring, nearly planar with the naphthone ring and the distances from C1 atom of acetyl group to mean plane of the three
six-membered ring is 0.112(3) Å. Moreover, the structure is stabilized by intermolecular C-H···π and π-π stacking interactions.
Key Words: Naphthol, Synthesis, Supramolecular structure.
Naphthaldehyde, hydroxy-naphthaldehyde and their
MoK radition (λ = 0.71073 Å) at 298(2) K. The structure
α
1
-3
derivatives are an important class of intermediates which
was solved by using the program SHELXS-97 and Fourier
difference techniques and refined by full-matrix least-squares
4,5
condenses with primary amines to afford Schiff bases that
are one of most versatile mixed-donor ligands in the field of
2
method on F using SHELXL-97. Details of the data collection
6
-8
coordination chemistry . In this paper, we report on the
synthesis and the X-ray single-crystal structure of the 2-acetyl-
and refinements of the title compound are given in Table-1.
The non-hydrogen atoms were refined anisotropically. Hydrogen
atoms were added theoretically. CCDC: 712170.
1
-naphthol.
A sample of 2-methoxy naphthalene was obtained from
Alfa Aesar and used without further purification. The other
reagents and solvents were analytical grade reagents from
Tianjin Chemical Reagent Factory. C, H and O analyses were
carried out with a GmbHVariuoELV3.00 automatic elemental
analyzer. X-Ray single crystal structure was determined on a
Bruker Smart 1000 CCD area detector. Melting points were
measured by the use of a microscopic melting point apparatus
made in Beijing Taike Instrument Limited Company and the
thermometer was uncorrected.
TABLE-1
CRYSTAL DATA AND STRUCTURE REFINEMENT
FOR THE 2-ACETYL-1-NAPHTHOL
Empirical formula
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
C H O
12 10 2
186.20
298(2)
0.71073
Monoclinic
P 2 /n
1
a = 7.6246(9), b = 7.0312(7), c =
Cell dimensions, (Å, deg)
17.4709(16), β = 92.432(1)
Synthesis: A solution of 2-methoxy naphthalene (0.1
mmol), acetyl chloride (0.1 mmol) in 30 mL ethanol in the
3
Volume (Å )
935.77(17)
4
1.322
0.089
Z
presence of AlCl was refluxed for 5 h and then cooled to
3
3
Density (calculated) (mg/m )
Absorption coefficient (mm )
F(000)
Index ranges
Reflections collected
Independent reflections
Data/restraints/parameters
Goodness of fit indicator
R [I > 2σ(I)]
room temperature and filtered. Pale-yellow needle-like single
crystals suitable for X-ray diffraction studies were obtained
after several weeks by slow evaporation from a methanol-ethyl
ether (1:3) mixed solution of the title compound.
X-Ray structure determination: The single crystal of
the 2-acetyl-1-naphthol, with approximate dimensions of 0.55
mm × 0.50 mm × 0.38 mm was placed on a Bruker Smart
-1
392.0
-9 ≤ h ≤ 8, -8 ≤ k ≤ 7, -20 ≤ l ≤ 19
4497/1643 [R(int) = 0.0454]
1494
1643/0/129
1.071
R = 0.0421, wR = 0.1332
1 2
Largest diff. peak and hole (e Å ) 0.152 and -0.154
1000 diffractmeter equipped withApex CCD area detector. The
-3
diffraction data were collected using a graphite monochromated
Su, Qiong
