Antibacterial activity and global reactivity descriptors of some newly synthesized unsymmetrical sulfamides

Article abstract of DOI:10.13005/ojc/320205

In the present study a series of unsymmetric linear sulfamides (1-9) starting from a primary amine were synthesized and their structures were confirmed by elemental analyses, mass spectrometry and1 H NMR techniques. All the synthesized compounds were scre

Full text of DOI:10.13005/ojc/320205

ISSN: 0970-020 X
CODEN: OJCHEG
2016, Vol. 32, No. (2):
Pg. 799-806
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Antibacterial Activity and Global Reactivity Descriptors of
some Newly Synthesized Unsymmetrical Sulfamides
AMEL BENDJEDDOU1*,TAHAR ABBAz1,3, ADEL AYARI1, MERzOUG BENAHMED2,
ABDELkRIM GOUASMIA3 and DIDIER VILLEMIN4
1Laboratory of Aquatic and Terrestrial Ecosystems, Organic and Bioorganic
Chemistry group, University of Souk Ahras, Algeria.
2Laboratory of Bioactive Molecules and Applications, University of Tebessa, Algeria.
3Laboratory of Organic Materials and Heterochemistry, University of Tebessa, Algeria.
4Laboratory of Molecular and Thio-Organic Chemistry, UMR CNRS 6507, INC3M, FR 3038,
Labex EMC3, ensicaen & University of Caen, Caen 14050, France.
*Corresponding author E-mail: bendjeddouamel@gmail.com
http://dx.doi.org/10.13005/ojc/320205
(Received: February 03, 2016; Accepted: March 27, 2016)
ABSTRACT
In the present study a series of unsymmetric linear sulfamides (1-9) starting from a
primary amine were synthesized and their structures were confirmed by elemental analyses, mass
1
spectrometry and H NMR techniques. All the synthesized compounds were screened for their
antibacterial activities by both disc diusion and minimal inhibition concentration (MIC) methods.
Frontier molecular orbital (FMO) analysis and global reactivity descriptors have been performed
using the density functional theory (DFT) with the B3LYP functional.The results indicated that these
derivatives, depending of their substituted radical, bring about an improvement in the bacterial
activity.
keywords: Unsymmetric Sulfamides, Antibacterial Activity, Global Reactivity,
Minimum Inhibitory Concentrations (MIC).
INTRODUCTION
of drugs, with several types of pharmacological
activities including antibacterial3 anti-carbonic
anhydrase4 diuretic5 hypoglycemic6 and antithyroid
activity7. Sulfonamides were primarily developed
as antibacterial agents, with sulfanilamide the first
recognized sulfonamide antibacterial. Since then
many other effective antibacterial derived from
sulfonamides have been discovered and utilized
in medicine. These classes of compounds are
Sulfonamides (sulfa drugs) were the first
drugs largely employed and systematically used as
preventive and chemotherapeutic agents against
various diseases1. They are active against a broad
range of Gram-positive and Gram-negative bacteria
and function as competitive antagonists to bacterial
folate synthesis2.They constitute an important class

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BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
Minimum Inhibitory Concentrations
considered as “scalffolds” in medicinal chemistry
to drug development with different biological (MICs) values, defined as the lowest concentration
activities. In organic chemistry, these compounds of sample which inhibits the visible growth of
have a functional application in the industry in microorganism after overnight incubation, were also
some products of health, food colorants and others; determined by the broth dilution method following the
therefore it is necessary to continue with research procedures recommended by the CLSI (Clinical and
projects that help to synthesize new compounds with Laboratory Standarts Institute)14.
sulfonamide group.
Synthesis and Characterization of unsymmetrical
In light of these, we became interested sulfamides 1-9
in the synthesis, characterization and biological
A solution of sulfuryl chloride (1 equiv, 10
evaluation of unsymmetric linear sulfamides. In mmol, 1.35 g) in hexane (30 ml) was added dropwise
order to assess more accurately and to provide a to a stirred solution of the first amine (1 equiv, 10
background frame work for the work described in mmol) and the second amine (1 equiv, 10 mmol) in
this paper, a correlation between biological activity hexane (80 ml) cooled to 0°C. The reaction mixture
and some appropriate quantum descriptors8-9 such was stirred for 6h, then it was extracted with CH2Cl2
as EHOMO, ELUMO, energy gap, global hardness, (200 ml), the organic phase was washed with 120 ml
global hardness softness, electrophilicity index of 1M HCl, followed with water (120 ml), and dried
and molecular electrostatic potential have also with Na2SO4 and the solvent was removed under
been carried out from the density functional theory reduced pressure to give the crude as colorless
(DFT).
oil. Compounds 1-9 were obtained by column
chromatography of the residue (silica gel, eluting
with (AcOEt / n-Hexane: 6/4).
EXPERIMENTAL
General
N-(thiophen-2-yl methyl)-N’-(tert-butyl)
NMR spectra were recorded on a WP 400- sulfamide 1
NMR instrument. FAB mass spectra were recorded
Beige powder. Yield: 25%. M.p.: 155°C.
1
on a JOEL JMS-DX 300 spectrometer. Uncorrected TLC: Rf = 0.74 (AcOEt / n-Hexane: 6/4). H NMR
melting points were measured on a 510 Buchi (400 MHz, CDCl3, d, ppm): 1.40 (s, 9H, tBu); 3.93 (s,
apparatus. Density functional theory calculations 2H, CH2-N-thio); 4.30 (s, 1H, NH-tBu); 4.45 (s, 1H,
were carried out using the Gaussian 09W program NH-thio); 6.63 (d, 1H, J = 3.60 Hz, thio ); 6.75 (t,1H,
packages developed by Frisch and coworkers10.The J = 4.45 Hz, thio); 6.95 (d, 1H, J = 4.45 Hz, thio).
Becke’s three parameter hybrid functional using the MS (NOBA, FAB > 0): 627 [M + H]+. Anal. calcd for
LYP correlation functional (B3LYP), one of the most C9H16N2O2S2: C, 43.52%; H, 6.49; S, 25.82%; found:
robust functional of the hybrid family, was herein C, 43.67%; H, 6.59%; S, 25.60%.
used for all the calculations, with 6.31G (d, p) basis
set11-12. Gaussian output files were visualized by N-(thiophen-2-yl methyl)-N’-(isopentyl)
means of gaussian view 05 software13. All solvents sulfamide 2
were dried by standard methods and all commercial Beige powder. Yield: 28%. M.p.: 149°C. TLC: Rf =
reagents used without purification.All reactions were 0.80 (AcOEt / n-Hexane: 6/4). 1H NMR (400 MHz,
performed under an inert atmosphere of nitrogen.
CDCl3, d, ppm): 1.10 (d, 6H, 2CH3); 1.60 (m, 2H,
CH2); 1.90 (m, 1H, CH-(CH3)2); 2.75 (t, 2H, CH2-N);
Inhibition zones (DZI) of the compounds 4.26 (s, 1H, NH-isopro);4.45 (s, 1H, NH-thio);3.93 (s,
were examined by disc diffusion technique14-15
2H, CH2-N-thio); 6.63 (d, 1H, J = 3.60 Hz, thio); 6.75
.
The Antibacterial screening was performed using (t,1H, J = 4.45 Hz, thio);6.95 (d, 1H, J = 4.45 Hz, thio
Mueller–Hinton agar for 24 hrs at 37°C. After ). MS (NOBA, FAB > 0): 627 [M + H]+. Anal. calcd for
incubation, the zone of growth inhibition around the C10H18N2O2S2:C, 45.77%;H, 6.91;S, 24.44%;found:
disks was measured in millimeter (mm). All tests C, 46.00%; H, 7.10%; S, 24.25%.
were performed in duplicate, and experiment was
repeated three times.

BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
801
N-(thiophen-2-yl methyl)-N’-(isobutyl)
sulfamide 3
for C11H19N3O2S: C, 51.33%; H, 7.44; S, 12.46%;
found: C, 51.48%; H, 7.59%; S, 12.61%.
Beige powder. Yield: 26%. M.p.: 151°C.
TLC: Rf = 0.77 (AcOEt / n-Hexane: 6/4). 1H NMR
(400 MHz, CDCl3, d, ppm): 1.06 (d, 6H, 2CH3); 2.00
(m, 1H, CH(CH3)2); 2.65 (d, 2H, CH2-N); 3.93 (s,
2H, CH2-N-thio); 4.28 (s, 1H, NH-iBu); 4.45 (s, 1H,
NH-thio); 6.63 (d, 1H, J = 3.60 Hz, thio ); 6.75 (t,1H,
J = 4.45 Hz, thio); 6.95 (d, 1H, J = 4.45 Hz, thio).
MS (NOBA, FAB > 0): 627 [M + H]+. Anal. calcd for
C9H16N2O2S2: C, 43.52%; H, 6.49; S, 25.82%; found:
C, 43.77%; H, 6.58%; S, 25.53%.
N-(pyridin-4-yl methyl)-N’-(isobutyl)sulfamide 6
Scarcely green powder. Yield: 31%. M.p.:
145°C. TLC: Rf = 0.63 (AcOEt / n-Hexane: 6/4). 1H
NMR (400 MHz, CDCl3, d, ppm): 1.06 (d, 6H, 2CH3);
2.00 (m, 1H, CH(CH3)2); 2.65 (d, 2H, CH2-N); 3.96
(d, 2H, J = 4.66 Hz, CH2-pyr); 4.28 (s, 1H, NH-iBu);
4.50 (s, 1H, NH-pyr) 7.45 (d, 2H, J = 4.65 Hz, pyr);
8.72 (d, 2H, J = 4.68 Hz, pyr). MS (NOBA, FAB > 0):
627 [M + H]+.Anal.calcd for C10H17N3O2S:C, 49.36%;
H, 7.04;S, 13.17%;found: C, 49.51%;H, 7..15%;S,
13.22%.
N-(pyridin-4-yl methyl)-N’-(tert-butyl)
sulfamide 4
Scarcely green powder. Yield: 30%. M.p.:
147°C. TLC: Rf = 0.61 (AcOEt / n-Hexane: 6/4). 1H
NMR (400 MHz, CDCl3, d, ppm): 1.40 (s, 9H, tBu);
3.96 (d, 2H, J = 4.66 Hz, CH2 -pyr); 4.30 (s, 1H,
NH-tBu); 4.50 (s, 1H, NH-pyr) 7.45 (d, 2H, J = 4.65
Hz, pyr); 8.72 (d, 2H, J = 4.68 Hz, pyr). MS (NOBA,
FAB > 0): 627 [M + H]+. Anal. calcd for C10H17N3O2S:
C, 49.36%; H, 7.04; S, 13.17%; found: C, 49.60%;
H, 7.17%; S, 13.25%.
N-(benzyl)-N’-(tert-butyl)sulfamide 7
White powder. Yield: 21%. M.p.: 136°C.
TLC: Rf = 0.70 (AcOEt / n-Hexane: 6/4). 1H NMR
(400 MHz, CDCl3, d, ppm): 1.40 (s, 9H, tBu); 4.15
(d, 2H, J = 5.99 Hz, CH2 -Ph); 4.30 (s, 1H, NH-tBu);
4.47 (s, 1H, NH-Bn); 7.30 (m, 5H, ArH). MS (NOBA,
FAB > 0): 627 [M + H]+. Anal. calcd for C11H18N2O2S:
C, 54.51%; H, 7.48; S, 13.23%; found: C, 54.67%;
H, 7.59%; S, 13.35%.
N-(pyridin-4-yl methyl)-N’-(isopentyl)
N-(benzyl)-N’-(isopentyl)sulfamide 8
sulfamide 5
White powder. Yield: 24%. M.p.: 130°C.
Scarcely green powder. Yield: 33%. M.p.:
142°C. TLC: Rf = 0.66 (AcOEt / n-Hexane: 6/4). 1H
NMR (400 MHz, CDCl3, d, ppm): 1.10 (d, 6H, 2CH3);
1.60 (m, 2H, CH2); 1.90 (m, 1H, CH-(CH3)2); 2.75
(t, 2H, CH2-N); 3.96 (d, 2H, J = 4.66 Hz, CH2 -pyr);
4.26 (s, 1H, NH-isopro); 4.50 (s, 1H, NH-pyr) 7.45
(d, 2H, J = 4.65 Hz, pyr); 8.72 (d, 2H, J = 4.68 Hz,
pyr). MS (NOBA, FAB 0): 627 [M + H]+. Anal. calcd
TLC: Rf = 0.75 (AcOEt / n-Hexane: 6/4). 1H NMR
(400 MHz, CDCl3, d, ppm): 1.10 (d, 6H, 2CH3); 1.60
(m, 2H, CH2); 1.90 (m, 1H, CH-(CH3)2); 2.75 (t, 2H,
CH2-N); 4.15 (d, 2H, J = 5.99 Hz, CH2 -Ph); 4.26 (s,
1H, NH-isopro); 4.47 (s, 1H, NH-Bn); 7.30 (m, 5H,
ArH) .MS (NOBA, FAB > 0):627 [M + H]+.Anal.calcd
for C12H20N2O2S: C, 56.22%; H, 7.86; S, 12.50%;
found: C, 56.33%; H, 8.02%; S, 12.43%.
H
N
H
N
H
N
O
SO2Cl2
O
O
NH2
NH2
R2
S
R2
R1
S
R2
R1
S
R1
R2
R1
N
n-Hexane
N
N
O
O
O
H
H
H
1-9
R2 = tert-butyl
R2 = isopentyl
R2 = isobutyl
R2 = tert-butyl
R2 = isopentyl
R2 = isobutyl
R2 = tert-butyl
R2 = isopentyl
R2 = isobutyl
1: R1 = thiophen-2-yl methyl
2: R1 = thiophen-2-yl methyl
3: R1 = thiophen-2-yl methyl
4: R1 = pyridin-4-yl methyl
5: R1 = pyridin-4-yl methyl
6: R1 = pyridin-4-yl methyl
7: R1 = benzyl
R1 = thiophen-2-yl methyl, pyridin-4-yl methyl, benzyl
R2 = tert-butyl, isopentyl, isobutyl
8: R1 = benzyl
9: R1 = benzyl
Scheme 1: Synthetic Route For The Preparation Of Dissymmetric Sulfamides Derivatives 1-9

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BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
N-(benzyl)-N’-(isobutyl)sulfamide 9
In Vitro Antibacterial Activity
The title compounds containing thiophene
White powder. Yield: 22%. M.p.: 133°C.
1
TLC: Rf = 0.73 (AcOEt / n-Hexane: 6/4). H NMR (Series 1), pyridine (Series 2) and benzyl (Series
(400 MHz, CDCl3, d, ppm): 1.06 (d, 6H, 2CH3); 2.00 3) moieties were screened for their in vitro
(m, 1H, CH(CH3)2); 2.65 (d, 2H, CH2-N); 4.15 (d, 2H, antibacterial activity against Enterobacteriaceae
J = 5.99 Hz, CH2 -Ph); 4.28 (s, 1H, NH-iBu); 4.47 (s, and Staphylococcus aures by using disk diffusion
1H, NH-Bn); 7.30 (m, 5H, ArH). MS (NOBA, FAB and micro dilution methods. The zones of inhibition
> 0): 627 [M + H]+. Anal. calcd for C11H18N2O2S: C, and the minimum inhibitory concentrations obtained
54.51%; H, 7.48; S, 13.23%; found: C, 54.43%; H, by the synthesized compound were furnished in
7.63%; S, 13.31%.
RESULTS AND DISCUSSION
Synthesis
Table 1. The results of preliminary bioassay of the
synthetic compounds revealed that the majority of the
synthesized compounds were fairly active against all
tested bacteria. As shown in the Table 1 and figure
2, the synthesized compounds exhibited a broad
In this work, we exploit a method developed spectrum of activity with MIC values 4 - 512 mg/mL
in previous works16-17, for the preparation of against Enterobacteriaceae and Staphylococcus
unsymmetrical sulfamides derived of primary amines. aures strains with MIC vary between 2 and
Unsymmetrical and symmetrical sulfamides can be 512 µg/ml.
prepared by the direct addition of sulfuryl chloride
to a mixture of two primary amines in cyclohexane
It was evident From Table 1 That the
or hexane at 0°C. As discussed in our previous compound 2of Series 1(thiophenemoiety)containing
work, we have also obtained three compounds: two isopentyl substituted have exhibited higher activity
symmetric sulfamides and the mixed sulfamide. than the compound 3 containing substituted isobutyl
TLC reveals unsymmetrical sulfamide formation moiety followed by the compound 1 containing
and it is located in the middle between the first and substituted tert-butyl moiety, their MIC values were
the second symmetric sulfamides. In this paper, we (4 - 32 - 64 µg/mL) against Enterobacteriaceae and
are interested to the separation of dissymmetric (2 - 4 - 16 µg/mL) against Staphylococcus aures,
sulfamides in order to estimate their antibacterial respectively.
activity.
Series 2 (pyridine moiety), among
In the H NMR spectra all synthetized compounds 4, 5, and 6 derived from pyridine,
1
compounds revealed the presence of amino group compound 5 was the most potent among their
protons signals as singlet around 4.26 - 4.45 series with MIC equal to 64 mg/ml (31mm) ,
ppm, 4.26 - 4.47 ppm and 4.26 - 4.50 ppm for the while the compounds 4 and 6 showed moderate
thiophene, benzyl and pyridine series, respectively. antibacterial activity with a MIC value equal to
Mass spectrometry analysis validated the structure 128 - 512 µg/ml against Staphylococcus Aures and
of the examined derivatives. In all compounds, Enterobacteriaceae.
fragmentation peaks confirmed the structure of the
analyzed molecules.
Series 3 (benzyl moiety), compounds 7 and
9 with tert-butyl and isobutyl as alkyls, respectively
showed moderate activity, their MIC values were
(128 - 512 µg/ml), Whereas compound 8 which also
contain a benzyl moiety but with isopentyl alkyl was
the most active among this series with a MIC value
equal to 32 - 64 µg/ml towards Staphylococcus aures
and Enterobacteriaceae, respectively.
In conclusion, Antibacterial Activity studies
indicate that isopentyl substituted sulfonamides
Fig. 1: Antibacterial activity against
Gram- and Gram+ strains

BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
803
of each series were more active than the other
members.
(DEgap = 5.81 eV), so it is the hardest molecule.
Molecule 1 has the highest HOMO energy (EHOMO
= -6.16 eV) that allows him to be the best electron
donor molecule; on the other hand the molecule 6
has the lowest LUMO energy (ELUMO = -0.863 eV) that
allows it to be the best electron acceptor molecule.
Theoretical calculation
The highest occupied molecular orbital
(HOMO), the lowest unoccupied molecular orbital
(LUMO) and HOMO and LUMO energy gaps for
compounds 1-9 calculated at DFT level in the 6-31G
basis set.The eigenvalues of LUMO and HOMO and
their energy gap reflect the chemical activity of the
molecule.LUMO as an electron acceptor represents
the ability to obtain an electron, while HOMO as an
electron donor represents the ability to donate an
electron.The smaller the LUMO and HOMO energy
gaps, the easier it is for the HOMO electrons to be
excited; the higher the HOMO energies, the easier
it is for HOMO to donate electrons; the lower the
LUMO energies, the easier it is for LUMO to accept
electrons. A hard molecule has a large energy gap,
and a soft molecule has a small gap.
Two important properties of any molecule
(M) are its gas-phase ionization potential (I) and its
electron affinity (A). The determination of I and A
allows the absolute electronegativity (c) and absolute
hardness (ç) parameters for M to be calculated.In the
most common case, I and A are related to the one-
electron orbital energies of the HOMO and LUMO,
respectively.Then (I—A) is simply the difference
in energy between the HOMO and the LUMO. Soft
molecules have a small energy gap. Low ‘I’ creates
a better electron donor and large ‘A’ makes a better
electron acceptor. For almost all of the commonly
used exchange-correlation functional, the HOMO
and LUMO energy are not close to the exact IP
and EA respectively but, excellent linear correlation
relationship exists between HOMO energies and
calculated IP and also between the negative of
the LUMO energies and calculated EA. Therefore
based on these linear correlation relationships,
the calculated HOMO and LUMO energies can be
used to semi quantitatively estimate the ionization
potential and electron affinity.
From theoretical calculations established,
it was found that the molecule 4 has the lowest
energetic gap (DEgap = 5.54 eV), so it is the softest
molecule and it is the best to be easily excited by
against, the molecule 3 has the highest energy gap
Table 1: zones Of Growth Inhibition And MIC
Values Of The Compounds 1-9
Bacterial strains Enterobac Staphylococcus
teriaceae
aures
Considering the above, compound 6 has
the greater electron affinity value (A = 0.86 eV)
which indicate that it is the best electron acceptor.
Compound 1 has the lowest ionization potential value
1
2
3
4
5
6
7
8
9
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
MIC (µg/ml)
DZI (mm)
20
64
18
4
24
16
22
2
20
4
36
256
31
64
30
128
18
256
16
32
13
128
Table 2: Some Energetic Properties Of
Compounds 1-9
18
32
33
512
31
64
30
256
14
512
13
64
13
512
Comp. EHOMO ELUMO
(eV) (eV)
DEgap
(eV)
I
A
(eV)
(eV)
1
2
3
4
5
6
7
8
9
-6.168 -0.389 5.778 6.168 0.389
-6.218 -0.407 5.811 6.218 0.407
-6.229 -0.411 5.818 6.229 0.411
-6.375 -0.834 5.541 6.375 0.834
-6.476 -0.857 5.619 6.476 0.857
-6.497 -0.863 5.634 6.497 0.863
-6.198 -0.241 5.957 6.198 0.241
-6.296 -0.261 6.035 6.296 0.261
-6.317 -0.268 6.049 6.317 0.268
MIC (µg/ml)

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BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
(I = 6.16 eV) which indicate that it is the best electron
donor.
All these parameters for compounds 1-9
have been listed in Table 3. According to these
parameters, the chemical reactivity varies with
Theoretical calculations were performed the structural of molecules. Chemical hardness
in order to investigate physico-chemical properties (softness) value of compound 4 is lesser (greater)
that may be related to the antimicrobial action of among all the molecules. Thus, compound 4 is
the studied compounds. The chemical reactivity found to be more reactive than all the molecules.
of the molecular systems has been determined Compound 6 possesses higher electronegativity
by the conceptual density functional theory39. value than all compounds so; it is the best electron
Electronegativity (c), chemical potential (µ), global acceptor.
hardness (h), global softness (S) and electrophilicity
index (w) are global reactivity descriptors and are
The values of w for compounds 1- 9 indicate
highly successful in predicting global reactivity that they are three series classified in the order, series
trends. A property of interest in this study was the of pyridine, thiophene and benzyl, successively.The
global electrophilicity index, which may give some pyridine group has the high value of electrophilicity
insight on the biological activity of compounds.
index which, shows that the compounds of this group
are a strong electrophiles than the thiophene and
benzyl groups respectively.
Fig. 2:The minimum inhibition concentration of compounds 1-9
Fig. 3:The inhibition zones of compounds 1-9

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BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
Fig. 4: Frontier orbitals and MESP surfaces for compounds 2, 5 and 8
CONCLUSION
Table 3:The Calculated Quantum Chemical
Parameters Of Compounds 1-9
In conclusion, a series of novel unsymmetric
linear sulfonamides (1-9) were synthesized and their
antibacterial activities were evaluated against some
bacterial strains. The HOMO, LUMO and MESP
surfaces are analyzed to discuss the chemical
reactivity patterns in the molecules. A number of
reactivity parameters have been calculated to further
explain their chemical reactivity.It was observed that
within each series, compounds 2, 5 and 8 containing
isopentyl alkyl showed the highest biological activity.
These new data of these compounds might be helpful
in the future development of sulfonamide analogues
as novel antibacterial agents.
Comp. µ (eV) c(eV)
h(eV) S(eV) w (eV)
1
2
3
4
5
6
7
8
9
-3.278 3.278 2.889 0.173 1.859
-3.312 3.312 2.905 0.172 1.887
-3.320 3.320 2.909 0.171 1.885
-3.604 3.604 2.770 0.180 2.338
-3.666 3.666 2.809 0.178 2.392
-3.680 3.680 2.817 0.177 2.397
-3.219 3.219 2.879 0.173 1.793
-3.278 3.278 3.017 0.166 1.784
-3.292 3.292 3.024 0.165 1.788

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BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
ACkNOWLEDGMENTS
and Technological Development, DGRS-DT) and
Algerian Ministry of Scientific Research.
This work was generously supported by
the (General Directorate for Scientific Research
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