Synthesis, characterization and crystallographic studies of 4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl] methylidene}hydrazono]ethyl}benzene- 1,3-diol

Article abstract of DOI:10.1007/s10870-013-0441-y

The title compound 4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl]methylidene} hydrazono]ethyl}benzene-1,3-diol (1) which is an azine moiety, has been synthesized by microwave irradiation technique. The characterization by IR and mass spectroscopy confirms the structure of (1). The crystal system, lattice parameters and molecular structure of (1) has been determined by single crystal X-ray diffraction technique. The crystallographic data for the compound (1) is being reported for the first time. Studies reveal that the compound exhibits intermolecular and intramolecular hydrogen bonding interactions in its crystal structure. The compound crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 11.8734(7) A; b = 9.6194(6) A; c = 27.2410(16) A; β = 96.435(3) A; V = 3091.7(3) A³ and D _calc = 1.278 Mg/m³ for Z = 8. The surface morphology of the crystalline compound has been studied by SEM analysis. SEM reveals the microcrystalline features of the compound under study.

Full text of DOI:10.1007/s10870-013-0441-y

J Chem Crystallogr (2013) 43:455–462
DOI 10.1007/s10870-013-0441-y
ORIGINAL PAPER
Synthesis, Characterization and Crystallographic Studies
of 4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl] methylidene}
hydrazono]ethyl}benzene-1,3-diol
•
Thomas O. Kurian Pranita Sadaphale
•
•
L. J. Paliwal P. K. Pandey M. B. Bagade
•
Received: 27 February 2013 / Accepted: 10 July 2013 / Published online: 26 July 2013
Ó Springer Science+Business Media New York 2013
Abstract The title compound 4-{(1E)-1-[(2E)-{[4-(dimeth
ylamino)phenyl]methylidene}hydrazono]ethyl}benzene-1,
3-diol (1) which is an azine moiety, has been synthesized by
microwave irradiation technique. The characterization by IR
and mass spectroscopy confirms the structure of (1). The
crystal system, lattice parameters and molecular structure of
(1) has been determined by single crystal X-ray diffraction
technique. The crystallographic data for the compound (1) is
being reported for the first time. Studies reveal that the com-
pound exhibits intermolecular and intramolecular hydrogen
bonding interactions in its crystal structure. The compound
crystallizes in the monoclinic space group P21/n with unit
SEM reveals the microcrystalline features of the compound
under study.
Keywords Azine ꢀ IR and mass spectrscopy ꢀ
Single crystal XRD ꢀ Intermolecular hydrogen
bonding ꢀ Intramolecular hydrogen bonding ꢀ
Scanning electron microscopy
Abbreviations
IR
Infrared
NLO
IR
Non linear optic
Infrared
˚
cell dimensions a = 11.8734(7) A; b = 9.6194(6) A; c =
˚
MS
Mass spectroscopy
3
˚
˚
˚
27.2410(16) A; b = 96.435(3) A; V = 3091.7(3) A and
Dcalc = 1.278 Mg/m3 for Z = 8. The surface morphology of
the crystalline compound has been studied by SEM analysis.
HPLC High performance liquid chromatography
TLC Thin layer chromatography
SXRD Single crystal X-ray diffraction
SEM
Scanning electron microscopy
Di-chloromethane
DCM
MeOH Methanol
KBr
Esds
Potassium bromide
Estimated standard deviations
T. O. Kurian (&)
Dr. (Mrs.) Ira Nimdeokar Post Graduate and Research Centre
for Chemistry, Hislop College, Temple Road, Civil Lines,
Nagpur 440001, Maharashtra, India
Introduction
e-mail: thomaskurian2@gmail.com
Hydrazines and their derivatives, particularly the Schiff’s
bases, constitute a versatile class of compounds in organic
chemistry. They are known to exhibit interesting biological
properties [1–5], such as anti-inflammatory, analgesic,
anticonvulsant, antitubercular, antibacterial and antifungal
activity. Schiff’s bases of sulphonamides are known to
exhibit anticancer [6] activity. Schiff’s bases are also
known to serve as a precursor for a large number of het-
erocyclic compounds. Some of them have been used as
ligands/complexing agents owing to their ability of easily
P. Sadaphale ꢀ L. J. Paliwal ꢀ P. K. Pandey
Post Graduate Teaching Department, Department of Chemistry,
Rashtrasant Tukdoji Maharaj Nagpur University Campus,
Nagpur, India
P. K. Pandey
Technology & Innovation, Diversey India Pvt. Ltd., Mumbai,
Maharashtra, India
M. B. Bagade
Department of Chemistry, Seth Kesarimal Porwal College,
Kamptee, Nagpur, India
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J Chem Crystallogr (2013) 43:455–462
Synthesis of 1-(2,4-dihydroxyphenyl) ethanone (a)
attaching to metal ions to form highly stable coordination
compounds [7–9]. Organic materials with delocalized p
electrons generally display a large non-linear optical
(NLO) response which renders it resourceful for various
applications such as optical communication, optical com-
puting, optical information processing, optical disk data
storage, laser fusion reactions and laser remote sensing
[10]. N,N-dimethylaniline based chromophores as present
in the title compound (1) are also known to display second
order NLO properties owing to the donor dimethylaniline
group visibly in conjugation with the ‘azine’ moiety of the
molecule[11] and the transparency of the crystal.
Zincchloride(freshlyfusedandpowdered)0.12 mol(16.5 g),
Glacial acetic acid (16 ml) and dry Resorcinol 0.1 mol
(11.0 g) was taken in a beaker and subjected to microwave
irradiation at 200 w for 2 min. The mixture was cooled to
room temperature and 50 ml dil. HCl (1:1) was added to it
with stirring. The soln. was cooled in an ice bath. The product
was then filtered, washed with water and crystallized from
100 ml (0.1 N) hot HCl soln. to yield the compound (a). The
product was checked for purity by thin layer chromatography
(TLC) and the melting point was noted and verified.
In recent years, there has been growing interest in
microwave assisted techniques in synthesis of organic
compounds, owing to several advantages such as reduced
time, easy work-up, reduced amount of solvents, etc. [12–
16] Here we report the facile synthesis of the title com-
pound 4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl]meth-
ylidene}hydrazono]ethyl}benzene-1,3-diol (1); by both
microwave assisted and conventional synthetic techniques
to compare the results. The Azine molecule (1) under
discussion has been synthesized by condensation of the
hydrazine Schiff’s base of resacetophenone (b) and
4-dimethylamino benzaldehyde. Single crystal X-ray dif-
fraction (SXRD) analysis of (1) has been done and the
crystallographic studies incorporated in this communica-
tion are being reported for the first time. The mixed Azine
(1) (Azine moiety flanked on either sides by N,N dimethyl
phenyl and resorcinol ring structures) is a suitable NLO
candidate as it has a non-centrosymmetric arrangement at
the molecular and bulk levels, which is one of the crucial
parmeters for NLO property in organic materials [17, 18].
Further studies to ascertain NLO property; such as study of
thermal and photochemical stability, electric field induced
second harmonic generation (EFISHG) or hyper-Rayleigh
scattering (HRS) [19–21] for the study of the molecular
first hyperpolarizability (b), has not been carried out and is
in the scope of study of the readers for the Azine molecule
(1) and related compounds. The article also includes
microcrystalline analysis of the compound by scanning
electron microscopy (SEM) and a detailed characterization
of the moiety by IR and HPLC mass spectroscopy.
Synthesis of (E)-4-(1-hydrazonoethyl) benezene-1,3-diol (b)
Compound (a) 0.01 mol (1.52 g) and hydrazine hydrate
0.01 mol (0.5 g) was taken in 10 ml distilled water and
subjected to microwave irradiation at 200 w for 2 min.
After completion of reaction as indicated by TLC, the
reaction mixture was cooled to room temperature, which
afforded the intermediate product (b). The compound was
filtered and washed with water.
Process I {Conventional Method for Synthesis
of Compound (1)}
Compound (b) 0.005 mol (0.83 g) & 4-dimethylamino
benzaldehyde 0.005 mol (0.75 g) was taken in a round
bottom flask, to it was added 10 ml ethanol and a drop of
glacial acetic acid. The reaction mixture was refluxed for
2–3 h or till the completion of reaction was indicated by
TLC. The reaction mixture was then poured in ice and
filtered in vacuum. It was crystallized from ethanol to
afford the desired title compound (1).
Process II {Microwave Synthesis of Compound (1)}
Compound (b) 0.005 mol (0.83 g), 4-dimethylamino benzal-
dehyde 0.005 mol (0.75 g) and a drop of glacial acetic acid
were taken in a conical flask. A minimum amount of ethanol
was added to it, enough to form a paste. The reaction mixture
was mixed with a glass rod and subjected to microwave irra-
diation at 200 w for 2 min. Completion of reaction was indi-
cated by TLC. Cold water was added to the flask and stirred for
a few minutes. Product obtained was filtered, dried and crys-
tallized from ethanol to afford the desired compound (1).
Experimental
Synthesis and Crystal Growth
4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl]methylidene}
hydrazono]ethyl}benzene-1,3-diol
The title compound (1) has been synthesized by two dif-
ferent processes; process I (conventional) and process II
(microwave). The flow chart of the synthetic scheme of
process II is indicated in Fig. 1.
Orangecrystallinecompound;Yield:ProcessI:71 %;Process
II: 76 %; M.pt.: 210 °C; FT-IR (cm-1): m(O–H) = 3428.90;
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J Chem Crystallogr (2013) 43:455–462
457
Fig. 1 Synthetic Scheme of the
Azine molecule (1)
Refinement
m(C = N) = 1606.01; m(C–H) = 2921.09; LC–MS (m/z):
[M??1] 298.2
Refinement of F2 against ALL reflections: The weighted
R-factor wR and goodness of fit S are based on F2, con-
ventional R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 [2sigma (F2)
is used only for calculating R-factors (gt) etc. and is not
relevant to the choice of reflections for refinement. R-fac-
tors based on F2 are statistically about twice as large as
those based on F, and R- factors based on ALL data will be
even larger.
Single Crystals of the compound were grown by slow
evaporation in DCM–MeOH solution (3:1 by volume) at
room temperature (*25–35 °C). A saturated solution of
the purified compound was made in DiChloroMethane and
Methanol (GR grade Merck). The solution was then filtered
to remove any suspended impurities and clear solution was
subjected to slow evaporation in glass tubes with a fine
hole in the stopper. Single crystals of good transparency
were obtained in 2 weeks time.
Geometry
Characterization Techniques
All estimated standard deviations (esds) (except the esd in
the dihedral angle between two l.s. planes) are estimated
using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in dis-
tances, angles and torsion angles; correlations between esds
in cell parameters are only used when they are defined by
crystal symmetry. An approximate (isotropic) treatment of
cell esds is used for estimating esds involving l.s. planes.
All the melting points were determined in an open capillary
tube and are uncorrected. Completion of the reaction has
been monitored by thin layer chromatography on pre-
coated sheets of silica gel-G. All the reagents used were
chemically pure and of AR grade. Solvents were dried and
distilled before use. Microwave irradiation has been carried
out in a Samsung MW71E oven, operating at 2450 MHz
with power output of 100 W/800 W. The IR spectra in KBr
has been recorded in the range of 4000–400 cm-1 on
Shimadzu spectrophotometer, Mass Spectra has been
recorded on a Shimadzu couple to Sciex, HPLC-Mass
Spectrometer. Scanning electron microscopy (SEM) of all
the samples were characterized with the help of analytical
scanning electron microscope Jeol JSM-6380 LA Japan.
Single crystal X-ray data has been collected on a Bruker
AXS Kappa Apex II CCD diffractometer using mono-
chromated Mo-Ka radiation.
Results and Discussion
Synthesis Techniques
The synthesis of intermediates and target compound were
performed as illustrated in Fig. 1. The intermediates (a) and
(b), synthesized by conventional techniques [22, 23] give
lesser % yields as compared to the microwave irradiation
technique as reported in the experimental part. The product
of condensation of hydrazine hydrate with an aromatic
aldehyde/ketone like resacetophenone (a) in this case, gives
a hydrazone (b). This intermediate further condenses with a
second mole of carbonyl compound preferably aromatic
aldehydes (4-dimethylamino benzaldehyde) to yield an
Data_collection: ‘APEX2 (Bruker, 2004)’; Cell refine-
ment: ‘APEX2/SAINT (Bruker, 2004)’; Data reduction:
‘SAINT/XPREP (Bruker, 2004)’; Structure solution: ‘SIR92
(Altornare et al., 1993)’; Structure refinement: ‘SHELXL-97
(Sheldrick, 1997)’; Molecular graphics: ‘ORTEP3 (Farrugia,
1997) and Mercury (Bruno et al., 2002)’; Publication
material: ‘SHELXL-97 (Sheldrick, 1997)’.
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J Chem Crystallogr (2013) 43:455–462
Fig. 2 Infrared spectra of the
Azine (1)
˚
Table 1 Hydrogen bonds for (1) [A and deg]
Infrared and Mass Spectroscopy
D–H
d(D–H) d(HꢀꢀA) \DHA d(DꢀꢀA)
A
The characteristic IR bands of the synthesized compounds are
presented in ‘‘sect. 2.1.5’’. The IR (KBr) spectra of the target
compound as shown in Fig. 2 reveals a broad peak at
3428.90 cm-1 indicating ArO–H absorption although at a
lower frequency than the standard frequency for phenolic
O–H stretch which is *3610 cm-1. For ascertaining the
phenolic O–H peak, the C–O stretch at 1248.76 cm-1 and
C=C stretch of cluster of peaks in pairs at 1600–1400 cm-1
range, are also observed and is thus confirmed [25]. The
compound also shows a distinct peak at 1606.01 cm-1 indi-
cating the R2C = N- imine stretching frequency, again at a
lower frequency than the standard range, 1690–1650 cm-1
O1–H1O1 0.820
O2–H2O2 0.820
O3–H3O3 0.820
1.857
1.786
1.882
166.24 2.661
146.76 2.512
161.11 2.671
O4
N3
O4 [-x ?
3/2, y-1/2,
-z ? 1/2]
O4–H4O4 0.820
1.840
146.79 2.566
N4
azine [24] which is the title compound (1). Spectroscopic
methods and SXRD reports together confirm the structure of
the target compound.
Fig. 3 Ortep Plot of two
independent molecules A and B
of the Azine (1) in solid state
with 50 % thermal ellipsoid
probability
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459
[26]. These anomalies in the decrease in stretching frequen-
cies can be attributed to the intramolecular and intermolecular
hydrogen bonding in the molecule as confirmed by SXRD
results, presented in ‘‘Sect. 3.3.1’’. Another broad peak around
2921.09 cm-1, possibly indicates sp2 = C–H stretching fre-
quency of the aromatic rings [27].
Table 2 Crystal data and structure refinement for (1)
Identification code
Empirical formula
Formula weight
shelxl
C17 H19 N3 O2
297.35
Temperature
296(2) K
˚
0.71073 A
Wavelength
The mass spectrum of compound (1) by HPLC–MS
shows the molecular ion peak at [M? ? 1] at 298.2 m/z.
Crystal system, space group
Unit cell dimensions
Monoclinic, P21/n
˚
a = 11.8734(7) A
alpha = 90°
b = 9.6194(6) A
Single Crystal X-Ray Crystallography
˚
beta = 96.435(3)°
˚
c = 27.2410(16) A
The structure of 4-{(1E)-1-[(2E)-{[4-(dimethylamino)
phenyl]methylidene}hydrazono]ethyl}benzene-1,3-diol (1)
has been confirmed by the result of a single crystal X-ray
structure determination. The crystal structure of the title
mixed azine contains two independent molecules A & B.
Experimental details for data collection and structure
refinement are summarized in Table 1. An ORTEP dia-
gram of the molecular structure of (1) in the crystal form
with the corresponding atom numbering scheme is shown
in Fig. 3.
gamma = 90°
3
˚
Volume
3091.7(3) A
Z, Calculated density
Absorption coefficient
F(000)
8, 1.278 Mg/m3
0.086 mm-1
1264
Crystal size
0.35 9 0.25 9 0.20 mm
1.50–28.41°
-15 B h B 13; -12 B k B 12;
-36 B l B 36
Theta range for data collection
Limiting indices
Reflections collected/unique
Completeness to theta = 28.41
Absorption correction
52719/7719 [R (int) = 0.0539]
99.4 %
Special Details
Semi-empirical from equivalents
0.9831 and 0.9706
Full-matrix least-squares on F2
Max. and min. transmission
Refinement method
The crystal structure and data reveals that the molecule (1)
crystallizes in the chiral space group and assumes the
(E,E)-configuration as other azines of the similar type [28].
Data/restraints/parameters
Goodness-of-fit on F2
7719/0/407
˚
The bond lengths of the N(1)–C(13) = 1.377(3) A and
1.033
˚
N(6)–C(30) = 1.365(2) A is a value intermediate between
Final R indices [I [ 2sigma(I)]
R indices (all data)
R1 = 0.0556, wR2 = 0.1598
R1 = 0.0963, wR2 = 0.1995
0.0066(13)
those for double and single C–N bonds. Similarly, the
observed decrease in the C–O and C–C lengths as seen in
Table 2, which when compared to the standard C–O and
C–C single bond lengths [29], indicate partial double bond
Extinction coefficient
-3
˚
0.551 and -0.369 e. A
Largest diff. peak and hole
Fig. 4 Computed molecular models of the Azine (1) depicting the hydrogen bond distances
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J Chem Crystallogr (2013) 43:455–462
˚
Table 3 Selected bond lengths [A] and torsion angles [deg] for the
Azine (1)
characteristics and the quinonoid structure of the molecule
predicts presence of extensive conjugation. Whereas the
observed N–N bond length of the azine bridge in the
molecule, according to the XRD data seems to be closer to
the standard value of N–N single bond; thus indicating the
presence of single bond like characteristics. This is
because, the azine bridge is known to decrease the
molecular dipole moment in case of unsymmetrical aryl
azines and such azine bridges are considered to be ‘‘con-
jugation stoppers’’ [30]. This behaviour of the azines was
verified and reported by electrochemical methods which
provide data supporting single bond character of the N–N
N(1)–C(13)
N(6)–C(30)
O(1)–C(3)
O(2)–C(5)
O(3)–C(20)
O(4)–C(22)
C(7)–C(6)
C(10)–C(9)
1.377(3) C(26)–C(27)
1.365(2) N(2)–N(3)
1.359(2) N(4)–N(5)
1.341(2)
1.444(2)
1.395(2)
1.377(2)
1.354(2) C(9)–N(2)–N(3)–C(7)
176.74(18)
1.312(2) C(24)–N(4)–N(5)–C(26) -174.81(16)
1.460(3)
1.443(3)
C(23)–C(24) 1.438(2)
Fig. 5 Computed crystal
packing structure of the
Azine (1)
Fig. 6 Figure indicating the angle subtended by the mean planes of molecules contained in the two different layers of the packing structure of
the Azine (1)
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461
bond and evidence for a lack of strong electronic com-
munication between the two aryl centers through the azo-
methine bonds in azines [31].
Study of torsion angles also reveals that the molecule in
spite of its quinonoid characteristics is not perfectly planar.
The conformation about the azine bridge of the molecule A is
N–N trans with a torsion angle of C(9)–N(2)–N(3)–
C(7) = 176.74(18)° and that of the molecule B about C(24)–
N(4)–N(5)–C(26) = -174.81(16)°. The phenyl rings are
also somewhat twisted with respect to the plane defined by
the ipso-carbon atoms of the phenyl rings and the imine
bond. Non-coplanarity is established by observing that the
mean plane passing through the N,N dimethyl phenyl ring
subtends an angle of 7.11° in molecule A and 11.68° in
molecule B respectively, with the mean plane passing
through the resorcinol ring moieties of each molecule thus
rendering them slightly non-planar. The results further point
out that the molecules are bonded with each other by inter-
molecular hydrogen bonding between the phenolic-O–H at
C3 of one molecule and the phenolic-oxygen at C22 of the
adjacent molecule. The molecule also shows intramolecular
hydrogen bonding between the phenolic-O–H at C5 and the
nitrogen N3 and also between phenolic-O–H at C22 and the
nitrogen N4, by a virtue of which, the coordination behaviour
of the compound maybe perhaps influenced; See Fig. 4. The
dotted lines depict the intermolecular hydrogen bonds and
the hanging hydrogen bond contacts with another set of
molecules. For complete hydrogen bonding details of (1),
refer Table 3.
Fig. 7 SEM image of (1) at 809
The packing diagram of the azine molecule (1) in its
crystal lattice is shown in Fig. 5. It crystallizes in the
monoclinic, P21/n space group with Z = 8. The crystal
packing structure of (1) shows a double layered pattern of 4
molecules of alternate molecules A and B, sandwiched
between parallel layers of 2 molecules of A and B each in the
unit cell. The mean planes of the molecules A of the two
different layers subtend an angle of 81.87°, thus indicating
the randomness/disorderliness in the packing structure; see
Fig. 6. There appears to be no T-contacts, neither any face to
face contacts [32] present among the arene rings of the azine
compounds in its packing structure. The crystal seems to be
stabilized by the intermolecular interactions.
Fig. 8 SEM image of (1) at 2509
Scanning Electron Microscopy
The SEM results of the purified crystalline compound
reveal that the molecule naturally crystallizes as plate-like
or lapped wafers like structures Fig. 7. On developing
single crystals by solvent/slow evaporation of the title
compound, it has been found to array itself in the similar
fashion. The surface morphology of the crystals clearly
reveals the presence of microcrystallites (7–10 lm) of
uniform shape throughout the structure Figs. 8, 9.
Fig. 9 SEM image of (1) at 3,5009
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Conclusion
To summarize, the article presents a facile, clean, and rapid
method for the synthesis of the title compound (1) using
microwave technique. The product yield has been found to
improve by 5 % by the microwave irradiation synthetic
scheme as compared to the conventional route of synthesis.
The spectroscopic analysis (IR & HPLC–MS) helps in
ascertaining the molecular structure. The microcrystalline
nature and the wafers-like morphology of the crystals
developed are clearly evident from the SEM images.
Finally, the structure has been resolved by SXRD method
which gives a deep insight about the molecular structure of
the compound, its geometry and lattice parameters.
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Supplementary Material
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Crystallographic data for the molecule (1) reported in this
paper have been deposited at the Cambridge Crystallo-
graphic Data Centre (CCDC) with quotation number
CCDC 915244. The data can be obtained free of charge via
www.ccdc.cam.ac.uk/data_request/cif, or by e-mailing to
data_request@ccdc.cam.ac.uk, or by contacting The
Director, CCDC, 12 Union Road, Cambridge CB2 1EZ,
UK; fax: ?44(0)1223-336033.
22. Baluja S, Solanki A, Kachhadia N (2006) J Iranian Chem Soc
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Gary M. Lampman, George S. Kriz, James R. Vyvyan., Ch. 2;
p 43
Acknowledgments The authors acknowledge SAIF, Cochin Univ.
of Science and Tech., Cochin, India; for the Single crystal XRD data
collection and analysis. One of the authors (T.O. Kurian) extends
gratitude to The Coordinator, P.G and Research Dept. of Chemistry,
to The Head, Dept. of Chemistry and to The Principal, Hislop Col-
lege, Nagpur, India; for extending the infrastructural facilities to carry
out the research study.
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