Application of SBA-Pr-SO3H in the green synthesis of isatinhydrazone derivatives: Characterization, UV-Vis investigation and computational studies

Article abstract of DOI:10.4067/S0717-97072016000200017

An efficient and green synthesis is developed for the preparation of the arylidene isatinhydrazone derivatives 4a-m using a heterogeneous mesoporous acid catalyst of SBA-Pr-SO₃H with a pore size of 6 nm under solvent free conditions. The hydrazones 4a-m were then analyzed by UV-Vis spectroscopy and the results were used for the calculation of the HOMO-LUMO band gap. In addition, the quantum chemical calculations were performed to provide an illustrative explanation for the obtained band gap; it is found that probably these molecules have a high tendency to donate electrons to the appropriate small-molecule acceptors with low energy and empty molecular orbital.

Full text of DOI:10.4067/S0717-97072016000200017

J. Chil. Chem. Soc., 61, Nº 2 (2016)
APPLICATION of SBA-Pr-SO3H IN THE GREEN SYNTHESIS OF ISATINHYDRAZONE DERIVATIVES:
CHARACTERIZATION, UV-Vis INVESTIGATION AND COMPUTATIONAL STUDIES
PARISA GHOLAMZADEHa, GHODSI MOHAMMADI ZIARANIa,*, ALIREZA BADIEIb
aDepartment of Chemistry, Alzahra University, Vanak Square, Tehran, 1993893973, Iran
bSchool of Chemistry, College of Science, University of Tehran, Tehran, Iran
ABSTRACT
An efficient and green synthesis is developed for the preparation of the arylidene isatinhydrazone derivatives 4a-m using a heterogeneous mesoporous acid
catalyst of SBA-Pr-SO H with a pore size of 6 nm under solvent free conditions. The hydrazones 4a-m were then analyzed by UV-Vis spectroscopy and the results
were used for the calcu3lation of the HOMO-LUMO band gap. In addition, the quantum chemical calculations were performed to provide an illustrative explanation
for the obtained band gap; it is found that probably these molecules have a high tendency to donate electrons to the appropriate small-molecule acceptors with low
energy and empty molecular orbital.
Keywords: Arylidene isatinhydrazone, SBA-Pr-SO3H, Green synthesis, HOMO-LUMO band gap, Small-molecule acceptors.
Synthesis of 3-Hydrazonoindolin-2-one (2)
INTRODUCTION
A mixture of isatin 1 (10 mmol, 1.47 g) and hydrazine monohydrate (80%,
5 ml) were heated under reflux condition. When the yellowish product was
observed and the reaction completed (monitored by TLC, 30 min), the mixture
was diluted with water and then, the product was dissolved in ethyl acetate
(3×20 ml). The organic phases were dried over MgSO4, filtered and the solvent
was evaporated in vacuo to obtain the pure product.
Hydrazone compounds are usually named after aldehydes and ketones
from which they are obtained. Hydrazones are one of the most important and
widespread classes of analytical reagents for the determination of different metal
ions using various analytical techniques.1 In addition, they have vast biological
properties for the treatment of tuberculosis, leprosy and mental disorders.2
For example, isonicotinoyl hydrazones are significant antitubercular agents.3
Some of hydrazones are also good insecticides, rodenticides, nematocides and
plant growth regulators.4 Isatinhydrazones as versatile Schiff bases can form
a variety of complexes5,6 and have different biological activities for instance
antimicrobial,7 antiglycation8 and antiproliferative9 activities.
3-Hydrazonoindolin-2-one (2)
Yellow powder, FT-IR (KBr): υ = 3356, 3153 (NH2), 1686 (C=O), 1655
(NH), 1587, 1550 and 1465 (aromatic C-C). 1H NMR (250 MHz, DMSO-D6):
d = 6.8 (d, J=7.5, 1H, Ar-H), 6.9 (t, J=7.5, 1H, Ar-H), 7.1 (t, J=7.5, 1H, Ar-H),
9H.5 (s, 1H, NH), 10.5 (s, 2H, NH2) ppm.
General procedure for the synthesis of arylidene isatinhydrazones (4a-m)
The SBA-Pr-SO3H (0.02 g which contains 0.024 mmol of loaded -SO3H)
was activated in vacuum at 100 ºC and then, after cooling to room temperature,
isatinhydrazone 2 (0.161 g, 1 mmol) and aldehyde derivatives (1 mmol) were
added to it. The mixture was heated in an oil bath (120 °C) in appropriate time
as shown in Table 2. After completion of the reaction which was monitored by
TLC, the crude product was dissolved in hot EtOH and then filtered to remove
the solid catalyst. The filtrate was cooled to give the pure product. The solid
acid catalyst subsequently was washed with hot EtOH, diluted acid solution,
distilled water and acetone, and dried under vacuum. It can be used for several
times without loss of significant activity.
Santa Barbara Amorphous (SBA-15) mesoporous silica was synthesized
for the first time in 1998 by Zhao and coworkers.10,11 SBA-15 is a hexagonal
mesoporous silica with good accessibility due to its high surface area, large
pore size, excellent stability (chemical and thermal), and easy isolation from the
products.12,13 The surface of SBA-15 can be modified with various functional
groups.14-18 In continuation of our previous studies,19-25 herein, we used the
propyl sulfonic acid functionalized SBA-15 (SBA-Pr-SO H) as a heterogeneous
solid acid catalyst in the synthesis of isatinhydrazone der3ivatives. Additionally,
at the present work, the relation between the structure and spectral properties
are determined through UV-Vis spectroscopy as well as quantum chemical
calculations. Then, the HOMO-LUMO analysis of isatinhydrazone compounds
are investigated. Moreover, the calculated results are compared with the
experimental results.
3-(Benzylidenehydrazono)indolin-2-one (4a)
Red powder, 3161 (NH), 3088 (aromatic C-H), 1728 (C=O), 1613 (NH),
1
1585, 1553 and 1458 (aromatic C-C). H NMR (250 MHz, CDCl ): d = 6.9
(d, J=8,1H, Ar-H), 7.1 (t, J=7.75, 1H, Ar-H), 7.38 (t, J=7.75, 1H,3Ar-HH), 7.5
(d, J=4, 3H), 7.9 (m, 2H), 8.1 (d, J=7.75, 1H, Ar-H), 8.5 (s, 1H, -N=CH-Ar),
8.6 (s, 1H, NH) ppm.
EXPERIMENTAL
The chemical compounds which were employed in this work, obtained
from Merck Company and used with no purification. Melting points were
measured by capillary tube method with an Electrothermal 9200 apparatus.
Infrared (IR) spectra were recorded from KBr disks using a Fourier-transform
(FT)-IR Bruker Tensor 27 instrument. 1H NMR (250 MHz) and 13C NMR (62.5
MHz) spectra were run on a Bruker DPX using tetramethylsilane (TMS) as
internal standard in CDCl3 and/or DMSO-d solution. Mass spectrometry (MS)
analysis was performed on a model 59736mass-selective detector (Agilent).
UV-Vis spectrum was run on Analytik Jena Specord® S600 spectrophotometer.
Scanning electron microscopy (SEM) analysis was performed on a Philips
XL-30 field-emission scanning electron microscope operated at 16 kV, while
transmission electron microscopy (TEM) was carried out on a Tecnai G2 F30
at 300 kV.
3-((3-Methoxybenzylidene)hydrazono)indolin-2-one (4g)
Brownish red crystal, 3171 (NH), 3090 (aromatic C-H), 2967 and 2857
(CH3), 1738 (C=O), 1616 (NH), 1593, 1544 and 1489 (aromatic C-C). 1H NMR
(250 MHz, CDCl ): dH = 3.9 (s, 3H, OCH3), 6.9-7.1 (m, 3H, Ar-H), 7.3-7.4 (m,
4H, Ar-H), 8.1 (d3, J=7.5, 1H, Ar-H), 8.5 (s, 1H, -N=CH-Ar), 9.65 (s, 1H, NH)
ppm. 13C NMR (62.5 MHz, CDCl ): dC = 55.4 (OCH3), 111.1, 113.2, 117.1,
118.2, 122.2, 123.2, 129.6, 130.0,3 133.5, 134.9, 143.8, 151.2, 160.0, 161.9,
166.8 ppm. MS (m/e): 280 (M++1, 4%), 279 (M+, 8%), 251 (100%), 236 (45%),
208 (15%), 118 (30%), 92 (30%), 77 (35%).
3-((3-Nitrobenzylidene)hydrazono)indolin-2-one (4i)
Orange powder, 3159 (NH), 3085 (aromatic C-H), 1743 (C=O), 1617
(NH), 1594, 1531 and 1460 (aromatic C-C). 1H NMR (250 MHz, DMSO-D6):
dH = 6.9 (d, J=22, 2H, Ar-H), 7.4 (s, 1H, Ar-H), 7.7 (m, 2H, Ar-H), 8.4 (s, 2H,
-N=CH-Ar), 8.6 (s, 2H, Ar-H), 10.9 (s, 1H, NH) ppm. 13C NMR (62.5 MHz,
DMSO-D6): dC = 111.4, 116.5, 122.9, 123.9, 126.5, 129.1, 131.2, 134.4, 134.5,
135.4, 145.6, 148.7, 150.4, 157.3, 164.7 ppm. MS (m/e): 294 (M+, 10%), 266
(100%), 220 (50%), 145 (15%), 118 (85%), 103 (45%), 91 (40%), 76 (55%).
3-((3-Phenylallylidene)hydrazono)indolin-2-one (4l)
Quantum chemical calculations
All of the quantum chemical calculations were accomplished using
Molecular Orbitals theory (Hückel calculation) via the ChemBioOffice 2008
(Ultra 11.0).
Synthesis and functionalization of SBA-15
The mesoporous SBA-15 was synthesized and functionalized according to
our previous publication19 and then, the obtained SBA-Pr-SO3H was used as a
mesoporous solid acid catalyst in the following reaction.
Yellow powder, 3148 (NH), 3094 (aromatic C-H), 3043 (=C-H), 1724
1
(C=O), 1623 (NH), 1603, 1543 and 1473 (conjugated and aromatic C-C). H
e-mail: gmziarani@hotmail.com
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J. Chil. Chem. Soc., 61, Nº 2 (2016)
NMR (250 MHz, CDCl ): d = 5.9 (s, 1H, trans -CH=CH-Ph), 6.4 (d, J=1.75,
1H, =CH-CH=CH-Ph),36.8H(d, J=7.75, 1H, -N=CH-), 7.0 (m, 2H, Ar-H), 7.2
(m, 1H, Ar-H), 7.45 (m, 3H, Ar-H), 7.6 (m, 3H, Ar-H), Ar-H, 8.7 (s, 1H, NH).
13C NMR (62.5 MHz, DMSO-D6): d = 77.2, 106.4, 110.8, 122.9, 124.4, 125.9,
128.9, 129.1, 129.4, 129.9, 130.0, 1C40.7, 141.3, 145.8, 174.1 ppm. MS (m/e):
276 (M++1, 25%), 275 (M+, 100%), 247 (90%), 157 (40%), 144 (85%), 132
(60%), 77 (50%).
RESULTS AND DISCUSSION
Functionalization of SBA-15 and its analysis
Mesoporous SBA-15 was prepared by using commercially available
triblock copolymer Pluronic P126 as a structure-directing agent.10,11 Then,
the surface of SBA-15 was firstly functionalized with (3-mercaptopropyl)
trimethoxysilane (MPTS) and followed by the oxidation of thiol groups
to sulfonic acid using hydrogen peroxide.26 As shown in Fig. 1, The SEM
image shows uniform particles about 1 μm as same morphology as SBA-15.
It illustrates that no changes occurred during the surface modifications and
morphology of the solid was remained. In addition, the TEM image exhibits
parallel channels that resemble the pore configurations of SBA-15. This
reveals that the pores of SBA-Pr-SO3H were not collapsed during the two-step
modification reaction.
Fig. 1: SEM and TEM images of SBA-Pr-SO3H
Synthesis of isatinhydrazones
In this paper, isatinhydrazone 2 was initially synthesized by the reaction of isatin 1 with excess amount of hydrazine monohydrate under reflux condition in
30 minutes (Scheme 1). Then, a simple and highly efficient strategy for the synthesis of arylidene isatinhydrazones was performed by the reaction of obtained
isatinhydrazone 2 and aromatic aldehydes 3a-m in the presence of SBA-Pr-SO3H (Scheme 1). To optimize the reaction conditions, isatinhydrazone 2 and
benzaldehyde 3a were subjected to the various conditions using a catalytic amount of SBA-Pr-SO3H. As shown by the results in Table 1, among the tested solvent-
free systems, the best result was achieved in the presence of SBA-Pr-SO3H, with the shortest reaction time (5 min) in high yield of the product. Nevertheless, the
effect of solvents was also investigated for this reaction in which the catalyst was not effective as well as a solvent free system. Furthermore, the weak catalyst
role of pure SBA-15 (Entry 6, Table 1) in this reaction emphasizes to this fact that the sulfonic acid functional groups onto the surface of SBA-15 accelerate the
reaction. Thus, the higher yields of this reaction are attributed to the effect of the nanopore size of about 6 nm of SBA-Pr-SO3H, which could act as a nanoreactor.
Scheme 1: Synthesis of isatinhydrazone 2 and its derivatives 4a-m
Table 1: The optimization of reaction condition for the synthesis of benzylidene isatinhydrazone 4a.
Entry
Solvent
Catalyst
-
Temperature (ºC)
Time
1 h
Yield (%)
1
2
3
4
5
6
-
120
120
80
95
-
-
SBA-Pr-SO3H*
SBA-Pr-SO3H*
SBA-Pr-SO3H*
SBA-Pr-SO3H*
SBA-15*
5 min
5 days
2/5 h
4 h
rt
90
EtOH
H2O
-
reflux
reflux
120
85
N.R.
85
1 h
*0.02 g
In order to evaluate the generality and versatility of this methodology,
isatinhydrazone 2 and aromatic aldehydes 3a-m in a molar ratio of 1:1 were
used in the optimum quantity of SBA-Pr-SO3H (0.02 g). Different arylidene
isatinhydrazone derivatives 4a-m were prepared successfully under solvent-
free condition. The results were good in terms of the reaction times and yields
and were summarized in Table 2. When the reaction was completed, the crude
product was dissolved in hot EtOH, and the catalyst was separated by a simple
filtration and reactivated by washing with hot EtOH and subsequently with a
dilute acid solution, water, and acetone for reusing without noticeable loss of
reactivity. The new products were characterized by Mass, FT-IR and NMR
spectroscopy data.
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J. Chil. Chem. Soc., 61, Nº 2 (2016)
Table 2: Synthesis of arylidene isatinhydrazones 4a-m in the presence of SBA-Pr-SO3H as catalyst.
Entry
No.
4a
4b
4c
4d
4e
4f
Ar
Time (min)
Yield (%)
m.p. (°C)
197-200
208-211
242-245
275-276
209-210
168-171
217-220
256-257
260-262
257-260
209-212
200-202
1
2
Ph
5
5
98
98
85
90
90
88
85
95
88
85
80
95
2-OH-C6H4
3-OH-C6H4
4-OH-C6H4
3-Cl-C6H4
2-OMe-C6H4
3-OMe-C6H4
2-NO2-C6H4
3-NO2-C6H4
4-F-C6H4
3
10
5
4
5
15
10
15
25
15
5
6
7
4g
4h
4i
8
9
10
11
12
4j
4k
4l
4-(NMe2)-C6H4
cinnamyl
10
5
13
4m
30
95
225-227
N
There are only a few reports for the synthesis of arylidene isatinhydrazone
derivatives 4 in which the product was obtained in an acidic condition (HCl
and/or H SO ) under refluxing for 3-5 h.6-8 In comparison with the existing
methods,2 the4 present methodology has several advantages such as greener
condition, shorter reaction time, easy work-up, and good yield with high
product purity.
solvent (Chart 1). The two λmax of isatinhydrazone 2 were observed at 275 and
330 nm (Chart 1-a), which are attributed to the π→π* and n→σ* transitions,
respectively. Among the arylidene isatinhydrazone derivatives, compounds
4a-j and 4l-m almost showed a similar UV-Vis spectrum, whereas 4k was
completely different. For example, compound 4a exhibited two absorptions
at 241 and 334 nm (see Chart 1b) related to the π→π* and n→σ* transitions,
respectively; while compound 4k shows these transitions at 342 and 243,
respectively (see Chart 1c).
UV-Vis spectroscopy and quantum chemical calculations
The experimental maximum absorption wavelengths (λ ) were found for
isatinhydrazone 2 and arylidene isatinhydrazone derivativesm4aax -m in ethanol as
Chart 1: UV-Vis spectrum of isatinhydrazone 2 and arylidene isatinhydrazone derivatives 4a-m in EtOH.
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J. Chil. Chem. Soc., 61, Nº 2 (2016)
The quantum chemical calculations of the compounds 2 and 4a-m were
performed using Molecular Orbitals theory (Hückel calculation) via the
ChemBioOffice 2008 to determine the highest occupied molecular orbital
(HOMO) and the lowest unoccupied molecular orbital (LUMO) providing
useful additional insights into the possibility of electron transfer between
HOMO and LUMO of the molecules. The corresponding HOMO and LUMO
density distributions of the compounds 2 and 4a are presented in Fig. 2. In
HOMO structure of 2, it is evident that the HOMO electron density is more
distributed on the nitrogen atoms of hydrazone moiety and some of the carbon
atoms, however, in LUMO structure, the density is diffused on the all atoms. In
HOMO structure of 4a, the density of electrons is distributed on the carbonyl
group and the nitrogen atoms of hydrazone moiety, but the LUMO structure
shows the electrons are distributed on the phenyl group. Therefore, the carbon
atoms in the C=N bond of the hydrazone moiety and the carbonyl group (in
the ground state of the molecules) are the active cites for the absorption of the
photons from the UV-Vis irradiation to convert the molecule from the HOMO
to LUMO form.
Fig. 2. Frontier molecular orbital density distributions of compounds 2 and 4a
E
is related to the electron donating ability of the molecule. The high
band gap energy, ΔE, from the λmax (Table 3). The λmax was obtained from the
UV-Vis spectra of each compound in EtOH (Chart 1). According to the prior
studies about the electron donating molecules,27-30 and based on the results in
Table 3, the high values of EHOMO for the molecules probably suggests that
these molecules have high tendency to donate electrons to a proper acceptor
molecule with low energy and empty molecular orbital.
value HoOfMOEHOMO indicates the molecule tendency to donate electrons. E
shows the ability of the molecule to receive electrons in which lower vaLlUuMeOs
of E
are more probable to accept electrons. Herein, the quantum chemical
paraLmUMetOers such as the energy of the HOMO and LUMO orbitals and the band
gap energy of 2 and 4a-m were calculated and are comprised with the calculated
Table 3: The quantum chemical parameters derived from compounds 2 and 4a-m.
Compound
No.
HOMO-LUMO gap
(ev) from E=hc/λmax
HOMO
predicted (ev)
LUMO
predicted (ev)
HOMO-LUMO gap (ev)
Predicted
Entry
λmax*(nm)
1
2
2
4a
4b
4c
4d
4e
4f
275
241
256
241
247
240
242
241
237
233
275
342
237
236
4.51
5.15
4.84
5.15
5.02
5.17
5.13
5.15
5.24
5.33
4.5
-7.86
-6.259
-5.00
-6.21
-5.90
-6.21
-6.08
-6.20
-7.06
-6.54
-5.89
-5.12
-6.91
-6.21
-1.86
-1.12
-0.527
-0.83
-1.07
-0.83
-0.52
-0.83
-4.72
-5.28
-1.07
-1.02
-2.23
-1.05
6.00
5.14
4.47
5.38
4.83
5.38
5.6
3
4
5
6
7
8
4g
4h
4i
5.37
2.34
1.26
4.82
4.10
4.68
5.16
9
10
11
12
13
14
4j
4k
4l
3.63
5.23
5.26
4m
*obtained from UV-Vis spectra
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J. Chil. Chem. Soc., 61, Nº 2 (2016)
28.- G. Tian, D. Wu, S. Qi, Z. Wu, X. Wang, Macromol. Rapid Commun., 32,
384, (2011).
CONCLUSIONS
29.- E. Y. H. Teo, Q.D. Ling, Y. Song, Y.P. Tan, W. Wang, E.T. Kang, D.S.H.
Chan, C. Zhu, Org. Electron., 7, 173, (2006).
30.- M. Bozorg, T. Shahrabi Farahani, J. Neshati, G. Mohammadi Ziarani, Z.
Chaghazardi, P. Gholamzadeh, F. Ektefa, Res. Chem. Intermed., 41, 6057,
(2015).
A highly efficient method for the synthesis of arylidene isatinhydrazones
4a-m has been developed in the solvent free reaction of isatinhydrazone 2 and
different aldehydes 3a-m using recyclable, environmentally benign and green
heterogeneous nano catalyst of SBA-Pr-SO3H. The simplicity of the reaction,
recovery of the nano solid acid catalyst without loss of reactivity, and high yield
of the products offer improvements over existing methods. Then, the absorption
spectra of the hydrazones 4a-m were obtained by UV-Vis spectroscopy and
the results were used for calculation of the HOMO-LUMO band gap. In order
to investigating the molecular orbitals of the products, the quantum chemical
calculations were performed. The results were compared with the obtained
HOMO-LUMO band gap from UV-Vis spectra and it was found that probably
these molecules have a high tendency to donate electrons to the appropriate
small-molecule acceptors with low energy and empty molecular orbital.
ACKNOWLEDGMENT
We gratefully acknowledge the financial support from the Research
Council of Alzahra University and the University of Tehran.
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