Asian Journal of Chemistry; Vol. 25, No. 9 (2013), 5076-5078
Synthesis and Crystal Structure of 2,2'-(1,2-Ethylenedioxy)bisbenzaldehyde O,O'-Diethyldioxime
*
LI ZHAO , YU-JIE ZHANG, SHOU-TING ZHANG, HONG-XIA GUO and QIAN CHENG
School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P.R. China
*Corresponding author: E-mail: zhaoli_72@163.com
(Received: 25 September 2012;
Accepted: 20 March 2013)
AJC-13141
The compound, 2,2'-(1,2-ethylenedioxy)-bis-benzaldehyde O,O'-diethyldioxime, has been synthesized by 2,2'-(1,2-ethylenedioxy)-bis-
benzaldehyde O,O'-diethyldioxime and ethoxyamine hydrochloride in ethanolic solution and characterized structurally by X-ray crystal-
lography. The molecule of the title compound adopts an extended conformation where the two oxime groups are apart from each other.
The two benzene rings are parallel to each other. In the crystal structure, intermolecular C7-H7···O2 hydrogen bonds link the molecules
forming an infinite 1D chain-like supramolecular structure.
Key Words: Bisoxime compound, Synthesis, Crystal structure.
measured by the use of a microscopic melting point apparatus
made in Beijing Taike Instrument Limited Company and the
thermometer was uncorrected.
2,2'-(1,2-ethylenedioxy) bisbenzaldehyde was synthesized
by refluxing of salicyaldehyde, sodium hydroxide and 1,2-
dibromoethane in ethanol-water mixture under nitrogen for
ca. 48 h11.
INTRODUCTION
Oxime-type compounds (-C=N-OR) are a kind of important
ligands containing N atoms, they are usually synthesized by
the condensation of ketones or aldehydes with hydroxylamine
etc.1. Much attention has recently been paid to the synthesis
and crystal structure of oxime-type compounds and their
derivatives2 because they can provide new topologies for func-
tional materials, in which coordination forms and functionality
are significant variables3, they also can accommodate one, two
or more metal centers and form homo- and heteronuclear metal
complexes serving as catalysts4, models of reaction centers of
metalloenzymes5, models of reaction centers of metallo-
enzymes6, nonlinear optical materials and molecular recognition
and biological agents7. They are also useful in constructing
supramolecular structures8. Thus, new materials can be
produced by using these compounds, which seem to be suitable
candidates for further chemical modifications9,10. Here, the
synthesis and crystal structure of 2,2'-(1,2-ethylenedioxy)-
bisbenzaldehyde O,O'-diethyldioxime has been reported
carefully.
2,2'-(1,2-Ethylenedioxy)bisbenzaldehyde O,O'-diethyl-
dioxime was synthesized analogously to the method reported
in the previous literature12. To a hot ethanol solution (15 mL)
of 2,2'-(1,2-ethylenedioxy)-bis-benzaldehyde (270.3 mg, 1.0
mmol) was first added an ethanolic solution (10 mL) of
ethoxyamine hydrochloride (390.2 mg, 4.0 mmol), then NaOH
(400 mg, 10 mmol). After the mixture had been stirred under
reflux for 4 h, 10 mL distilled water was added. Then the
solution was filtered and concentrated to about 15 mL over
night in 271 K. The resulting pale-yellow solid product was
filtered and washed successively with distilled water and
ethanol/hexane (1:4). The isolated compound was dried under
vaccum to yield 242.7 mg of the title compound. Yield 68.1
%. m.p. 337-338 K.Anal. calcd. for C20H24N2O4 (%): C, 67.40;
H, 6.79; N, 7.86. Found (%): C, 67.57; H, 6.61; N, 7.72.
Colourless needle-like single crystals suitable for X-ray
diffraction studies were obtained after about one week by slow
evaporation from a ethanol/H2O (3:1) solution of the title
compound.
EXPERIMENTAL
The reagents and solvents were analytical grade reagents
from Tianjin Chemical Reagent Factory. C, H and N analyses
were carried out with a GmbH VariuoEL V3.00 automatic
elemental analyzer. IR spectra in the range 400-4000 cm-1 were
recorded on aVERTEX70 FT-IR spectrophotometer using KBr
pellets. X-ray single crystal structure was determined on a
Bruker Smart 1000 CCD area detector. Melting points were
X-Ray structure determination: The single crystal of
the title compound, with approximate dimensions of 0.43 ×
0.09 × 0.06 mm3 was placed on a Bruker Smart 1000 diffrac-
tmeter equipped withApex CCD area detector. The diffraction