Aqueous extract of Shikakai; a green solvent for deoximation reaction: Mechanistic approach from experimental to theoretical

Article abstract of DOI:10.1016/j.molliq.2020.113133

This article describes a green method for regeneration of carbonyl compounds from various types of oxime compounds under microwave radiation using I₂ and aqueous saponin solution isolated from Shikakai. Effect of saponin concentration on yield percentage of regenerated different types of carbonyl compounds has been discussed. A correlation has been established between saponin concentration and yield percentage of carbonyl compounds. Mechanism of interaction between oxime and saponin is established on the basis of density functional theory. In addition, the quantum chemical parameters for saponin have been determined. Furthermore, electrostatic surface analysis of the saponin is carried out to confirm the mechanism of interaction between saponin and oximes.

Full text of DOI:10.1016/j.molliq.2020.113133

Journal of Molecular Liquids 309 (2020) 113133
Contents lists available at ScienceDirect
Journal of Molecular Liquids
journal homepage: www.elsevier.com/locate/molliq
Short Communication
Aqueous extract of Shikakai; a green solvent for deoximation reaction:
Mechanistic approach from experimental to theoretical
b
c,
Debadutta Das a, , Ashish K. Sarangi , Ranjan K. Mohapatra , Pankaj K. Parhi d,e, Ahmed Mahal f,g
,
⁎
⁎
Raghaba Sahu h, Md. Kudrat-E-Zahan i
Department of Chemistry, Sukanti Degree College, Subarnapur, Odisha, India
Department of Chemistry, School of Applied Sciences, Centurion University of Technology and Management, Odisha, India
Department of Chemistry, Government College of Engineering, Keonjhar, Odisha, India
School of Chemical Technology, KIIT Deemed to be University, Bhubaneswar, Odisha, India
Convergence Research Center for Development of Mineral Resources (DMR), Korea Institute of Geosciences and Mineral Resources (KIGAM), Daejeon, South Korea
Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sci-
ences, Guangzhou 510650, People's Republic of China
Guangzhou HC Pharmaceutical Co., Ltd, Guangzhou 510663, People's Republic of China
a
b
c
d
e
f
g
h
College of Pharmacy, Seoul National University, Seoul, South Korea
Department of Chemistry, Rajshahi University, Rajshahi, 6205, Bangladesh
i
a r t i c l e i n f o
a b s t r a c t
Article history:
This article describes a green method for regeneration of carbonyl compounds from various types of oxime com-
pounds under microwave radiation using I2 and aqueous saponin solution isolated from Shikakai. Effect of sapo-
nin concentration on yield percentage of regenerated different types of carbonyl compounds has been discussed.
A correlation has been established between saponin concentration and yield percentage of carbonyl compounds.
Mechanism of interaction between oxime and saponin is established on the basis of density functional theory. In
addition, the quantum chemical parameters for saponin have been determined. Furthermore, electrostatic sur-
face analysis of the saponin is carried out to confirm the mechanism of interaction between saponin and oximes.
© 2018 Elsevier B.V. All rights reserved.
Received 7 March 2020
Received in revised form 4 April 2020
Accepted 9 April 2020
Available online 17 April 2020
Keywords:
Shikakai
Regeneration of carbonyl compounds
Microwave radiation
DFT
ESP analysis
1. Introduction
et al. [5,6] have reported the selective oxidation of alcohols and depro-
tonation of oximes and imines to carbonyl compounds in aqueous
Use of green solvent and green methodology in chemical reactions
can conserve our environment. Therefore, development of eco-
friendly, pollution free and less cost effective chemical methodology is
an essential requirement for sustainability of the bio-system. Thus, or-
ganic reaction conducted in aqueous media being given more attentions
towards researcher [1,2]. Since most of the organic compound is nonpo-
lar and hence insoluble in water, the use of a phase transfer catalyst or
surfactant can effectively solubilize non polar organic compound in
polar aqueous medium. Surfactants aggregate have been found to be
suitable biphase systems for carrying out large number of reactions [3]
and substantial increase in the yield of product has been reported.
Boruah et al. have studied deoxygenation reaction of nitrones to cor-
responding imines and oximes to nitriles in hydrated media [4]. Gogoi
media. Oximes are easily synthesized from carbonyl compound and
are stable compound. Therefore, they are extensively used for the puri-
fication, identification and characterization of carbonyl compounds
[7,8]. Thus regeneration of carbonyl compounds from oximes provides
an alternative method for the preparation of aldehyde and ketones. Var-
ious types of metallic and nonmetallic reagents have been developed for
the regeneration of carbonyl compounds from oximes [9–14]. However,
most of the reported methods involve harmful and expensive metals,
toxic organic solvents, longer reaction time, difficulties in product puri-
fication and low product yields.
Shikakai, a saponin rich plant with scientific name Acacia concinna
belongs to the family Leguminosae (subfamily Mimoseae). This plant
is plentily available in the eastern as well as southern parts of India. Peri-
carps of its fruit contain surface-active component saponin, which is a
complicated mixture of saccharine derivatives and belong to a class of
naturally occurring non-ionic surfactant. Saponins isolated from Acacia
concinna is a triglycosides of acacia acid [15,16] containing glucose,
⁎
Corresponding authors.
E-mail addresses: deba.chemistry@gmail.com (D. Das),
ranjank_mohapatra@yahoo.com (R.K. Mohapatra).
https://doi.org/10.1016/j.molliq.2020.113133
0167-7322/© 2018 Elsevier B.V. All rights reserved.

2
D. Das et al. / Journal of Molecular Liquids 309 (2020) 113133
arabinose, and xylose as sugar moieties (called glycon) linked through
oxygen to the acacic acid moiety (called aglycone), (molecular structure
1) [17,18]. Saponin is amphiphilic in nature because of the presence of
both polar (Glycone part) and non-polar (Aglycone) part. Thus it can
solubilize the organic compound in aqueous condition. Hence aqueous
saponin solution can be used as a suitable replacement for organic
solvent.
with water and later on dried over anhydrous sodium sulphate. Evapo-
ration of solvent furnished by obtained crude products which on purifi-
cation through distillation and chromatography on silica gel
substantially yielded the corresponding carbonyl compounds (Scheme
1). The time length and product yield percentage are as presented in
Table 1.
Herein, we describe a simple and neutral method for regeneration of
oxime in good yield and reduced reaction time taking Iodine and an
aqueous saponin solution extracted from Acacia concinna under micro-
wave radiation for the regeneration of carbonyl compounds from
oxime. In this work, we have reported first time the mechanism of inter-
action between oxime and saponin on the basis of density functional
theory. In addition, the quantum chemical parameters for saponin
have been determined. Furthermore, electrostatic surface analysis of
the saponin is carried out to confirm the mechanism of interaction be-
tween saponin and oximes.
2.5. Computational evaluation (DFT calculations)
The saponin natural occurring compound was optimized and exam-
ined with the help of Gauss View 5.0.8 program [20]. The density func-
tional calculations were performed with GAUSSIAN 03 suit programs
[21–27]. For theoretical calculation B3LYP one exchange correlation
functional is used with 6-31 G (d, p) basic set for carbon, oxygen, hydro-
gen atoms.
3. Result and discussion
2. Experimental
3.1. Effect of saponin concentration on percentage of regeneration of car-
bonyl compounds
2.1. Preparation of aqueous saponin from Shikakai
Surfactant molecules constitute two components one is water insol-
uble hydrophobic component (their tails) and other is water soluble hy-
drophilic component (their heads). Thus due to their amphiphilic
nature it can solubilise organic molecule in its micellar core. Surfactant
has the unique property to form micelle in which various types of or-
ganic reaction can take place. This may be attributed to their electro-
static or hydrophobic interaction with reactants. [28]. Shikakai is a
saponin rich plant which is a naturally occurring non-ionic surfactant
and consists hydrophilic sugar chain and hydrophobic triterpene ring.
Therefore, it can solubilise the hydrophobic organic molecule in aque-
ous medium [5,29–32] (Scheme 2). The presence of acidic hydrogen in
saponins, solubilise the reactant species strongly by hydrogen bond for-
mation in aqueous medium which increases the number of favorable
collisions between the reactant species. It is found that above CMC
(0.019 g/cm3) there is no significant increase in percentage regenera-
tion of carbonyl compound. Thus there is maximum solubility of reac-
tant species oxime and iodine at CMC of saponin which may be the
optimized concentration for deoximation reaction.
The aqueous saponin from Shikakai is prepared as reported earlier
[19]. Accurately, 20 g of dry fruit of Shikakai was taken and the pericarp
of the fruit was converted to powdered form. Then it is dissolved in
200 mL of water and was subjected for agitation for 3 h by magnetic stir-
rer. The mixture is then centrifuged and filtrated to extract the active
component as saponin into the aqueous medium. The resulted extract
was used as a solublizing agent on regeneration study of carbonyl com-
pounds in the present study.
2.2. Calculation of critical micelle concentration (CMC)
The surface tension of the aqueous extract was measured by surface
tensiometer (Kyowa-350, Japan). For pure water surface tension is
found to be 72 mN/m and lowest value is obtained at 38 mN/m where
the concentration of surfactant reaches to 0.019 g per cm3 (1.9 wt%)
[19]. The minimum surface tension is achieved at 0.019 g/cm3, may be
the critical micelle concentration (CMC) of the dispersant [19]. This is
because above this concentration there is no further decrease in surface
tension value.
3.2. Mechanism of reaction
2.3. Preparation of oxime and carbonyl compound
The reactants oxime and I2 are nonpolar in nature and hence insolu-
ble in water. But in the presence of aqueous extract of Shikakai they are
solubilized in the micellar core of saponin. The generated electrophile I+
attacks at the carbon nitrogen double bond to form a cyclic structure
which facilitates the attack by an incoming water molecule to form car-
bonyl compounds (Fig. 1). The low yield of the compound 1m (Table 1)
may be due to its low solubility in micellar core because of more number
of nonpolar rings in the molecule.
Quick formation of the product in microwave assisted reaction is
achieved as water molecules absorb microwave radiation which is
transferred as heat energy to the reactants present in the medium and
easily activated to form the product. Thus, the deprotection of oximes
to corresponding carbonyl compounds gets promoted efficiently within
a few minutes with I2 and aqueous saponin under micro wave
The carbonyl compounds and reagents used for the preparation of
oximes are AR grade chemicals and further purified by standard proce-
dure. Triple distilled water is used throughout the experiment. The
products obtained in this investigation was ascertained from the char-
acterization results including elemental analyses, determination of
melting point, boiling point and direct comparison of the spectral data
to that of the authentic samples and reported. The IR and 1H NMR (in
deuterio chloroform) spectra were recorded by JASCO FT/IR-530 spec-
trophotometer and JFAL FX-90 instrument, respectively.
2.4. Method of regeneration of carbonyl compound
The mixture of oxime derivatives (1 mmol), a finely pulverized solid
iodine mass (2 mmol) and Shikakai extract (5 mL) were taken in an Er-
lenmeyer flask and then placed under microwave oven (2450 MHz fre-
quency) treatment by following a typical experimental procedure.
Different types of oximes were irradiated at different watts (internal
temp. ranging from 45–60 °C for different time period). TLC monitoring
showed the reaction progress and complete disappearance. The reac-
tion mixture was further cooled until it attains room temperature
followed by extraction with dichloromethane. The organic solvent
layer was subjected to washing using sodium thiosulphate and then
Scheme 1. Regeneration of carbonyl compounds from oxime.

D. Das et al. / Journal of Molecular Liquids 309 (2020) 113133
3
Table 1
Deprotection of ketoxime and aldoxime using iodine and Shikakai.
Entry
Substrates 1a–1m
Time
(Minutes)
MW
(Watts)
Products (2a–2m)
Yield (%)
⁎
In absence of Shikakai
In presence of Shikakai
1a.
1b.
1c.
1d.
1e.
1f.
1g.
1h.
1i.
Benzaldehyde oxime
Acetophenone oxime
Cyclohexanone oxime
2-Octanone oxime
3-phenyl propionaldehyde oxime
Hexanal oxime
Cyclohexyl methyl ketone oxime
2-Methoxy benzaldehyde oxime
3-Hydroxy benzaldehyde oxime
Benzophenone oxime
Benzyl acetone oxime
Cinnamaldehyde oxime
4-Chloro benzaldehyde oxime
6
8
100
100
100
100
100
100
100
100
100
170
160
160
170
21
19
14
16
11
13
14
12
15
–
89a
91a
78a
79a
64a
70a
83a
79a
83b
59b
66a
63a
62b
05
06
11
11
13
13
12
13
13
12
10
1j.
1k.
1l.
11
–
10
1m.
⁎
Yield refers to parent carbonyl compounds.
Purification by distillation.
Purification by column chromatography (ethyl acetate and petroleum ether) and crystallization from ethanol
a
b
irradiation. The conversion of oximes into carbonyl compounds can be
represented as shown in Fig. 1.
3.4. Frontier molecular orbitals approach
The FMOs studies are useful to explain the complex reaction and
predict the active site in a conjugate system. The energy of highest occu-
pied molecular orbital's (EHOMO) and energy of lowest unoccupied mo-
lecular orbital's (ELUMO) of the naturally extracted saponin compound
distinctly explain the global reactivity descriptors such as, chemical po-
tential, chemical hardness and electrophilicity. The negative values of
the highest occupied molecular orbital's energy (EHOMO) and lowest un-
occupied molecular orbital's energy (ELUMO) for the saponin compound
showing stability [35,36]. If we examine the electron cloud of the sapo-
nin, it is localized on the O109 - O113 and O115 – O118 (Fig. 2) for beneficial
of atomic sites for the nucleophilic attack position. The bond energy dif-
ference is prominently explained the chemical stability and chemical re-
activity of the active molecule [37]. The small energy difference values
clearly explain the reactivity of the saponin compound.
3.3. Theoretical calculation (molecular modelling)
The electronic properties are an important benchmark for chemistry.
Some of the important parameters such as single point energy and di-
pole moment (D) value of saponin are examined by using DFT/B3LYP
6-31+G (d, p) basic sets. From the lower single point energy value of sa-
ponin it is clear that the molecule is stable at their ground state [33,34].
The saponin possesses higher value of dipole moment for that it has
maximum dipole-dipole interaction (Table 2).
The Frontier Molecular Orbitals approach studies explains the chem-
ical reactivity of the saponin and the selection of the active sites from
the molecular system. The band energy clarification of Frontier Molecu-
lar Orbitals and the HOMO and LUMO energy gap describe the charge
transfer interaction. Some important chemical reactivity parameters
such as electronegativity (χ), chemical potential (μ), global hardness
(η), global electrophilicity index (ω) and global softness (S) [38,39]
are listed in (Table 3).
ðELUMO þ EHOMO
Þ
χ ¼ −
μ ¼ −χ ¼
η ¼
2
ðELUMO þ EHOMO
Þ
2
ðELUMO−EHOMO
Þ
2
1
S ¼
2η
μ2
ω ¼
2η
1
σ ¼
η
The highest occupied molecular orbital's energy (EHOMO) and lowest
unoccupied molecular orbital's energy (ELUMO) plots (Fig 3) of the sapo-
nin exact orbital energy gap between the mapped molecular orbitals.
Scheme 2. Solubilization of oxime and I2 in micellar core of Shikakai.

4
D. Das et al. / Journal of Molecular Liquids 309 (2020) 113133
Fig. 1. Mechanism for the conversion of oximes into carbonyl compounds (ref. [5]).
Table 2
Some important quantum chemical parameters such as chemical soft-
ness (S) of the saponin are more which clearly indicate the saponin
compound is more reactive with others. Other important parameter
such as the electrophilicity (ω) value assign as positive quantity which
measures the tendency of the system to accept electron from the
surrounding.
Energetic properties of the saponin calculated with the help of DFT/B3LYP 6.31+G (d,
P) basic sets.
Compound
Single point energy in kcal/mol
DFT/B3LYP 6.31G+ (d, P)
−6.5328 × 106
Dipole moment (D)
DFT/B3LYP 6.31G+ (d, P)
2.204
Saponin
Fig. 2. Optimized geometry of saponin.
Table 3
Calculated quantum chemical parameters for saponin.
Compound
HOMO in eV
LUMO in eV
ΔE in eV
χ Pauling
−0.1371
η in eV
σ
μ in eV
S
ω
eV
Saponin
−0.2234
−0.0508
0.1726
0.0609
0.1542
0.1371
8.2101
0.5199

D. Das et al. / Journal of Molecular Liquids 309 (2020) 113133
5
Fig. 3. HOMO-LUMO energy comparison of the saponin.
3.5. Electrostatic potential surface analysis
the formation of transition state is achieved quickly due to increase in
frequency of rotation of water molecules which in turn increases the en-
ergy content of the molecule. Thus the reaction can be completed within
a few minutes in comparison to other reported methods. The present
proposed investigation is a unique, innovative, and alternative green ap-
proach for conversion of oximes into the corresponding carbonyl com-
pounds with having greater efficacy over the existing traditional
methods. We have also reported first time the mechanism of interaction
between oxime and saponin on the basis of density functional theory. In
addition, the quantum chemical parameters for saponin have been de-
termined. Furthermore, electrostatic surface analysis of the saponin is
carried out to confirm the mechanism of interaction between saponin
and oximes.
The structure of saponin is optimized by applying molecular me-
chanics force field (MM+) followed by semiempirical PM3 methods.
The ESP surface of saponin is analyzed by using ArgusLab 4.0.1 software
(Fig. 4). The study displayed very specific data about the charge distri-
bution. The colour codes are in the range of −0.0500 (red) to
+0.0500 (white). The surface of saponin is clearly divided into two re-
gions. The negative region is related to electronegative site while the
positive region is related to electropositive sites. The negative region is
mainly over hydrophilic saponin as shown by red colour. Due to these
two distinct regions, it solubilises the non-polar organic compound in
polar solvent water. This may increase the rate of regeneration.
4. Conclusion
CRediT authorship contribution statement
Aqueous solution of saponin isolated from Acacia concinna is a green
and low cost solvent which effectively solubilise the oxime and iodine in
its micellar core. Therefore, it may be a suitable replacement of commer-
cial surfactant SDS, CTAB, SDBS etc. The activation energy required for
Debadutta Das: Conceptualization, Methodology, Supervision, Writ-
ing - original draft. Ashish K. Sarangi: Data curation, Formal analysis.
Ranjan K. Mohapatra: Conceptualization, Methodology, Supervision,
Writing - original draft. Pankaj K. Parhi: Data curation, Formal analysis.

6
D. Das et al. / Journal of Molecular Liquids 309 (2020) 113133
Fig. 4. ESP structure of saponin, (a) opaque structure, (b) mesh structure.
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The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influ-
ence the work reported in this paper.
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Acknowledgment
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