Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Br?nsted–Lewis acidic catalyst for the production of N,N′-alkylidene bisamides

Article abstract of DOI:10.1002/aoc.6046

In this research, a novel organic–inorganic hybrid salt, namely, N¹,N¹,N²,N²-tetramethyl-N¹,N²-bis(sulfo)ethane-1,2-diaminium tetrachloroferrate ([TMBSED][FeCl₄]₂) was

Full text of DOI:10.1002/aoc.6046

Received: 3 May 2020
DOI: 10.1002/aoc.6046
Revised: 24 August 2020
Accepted: 19 September 2020
F U L L P A P E R
Synthesis and characterization of a novel organic–inorganic
hybrid salt and its application as a highly effectual
Brønsted–Lewis acidic catalyst for the production of
N,N0-alkylidene bisamides
Abdolkarim Zare
| Fatemeh Monfared
| Seyed Sajad Sajadikhah
Department of Chemistry, Payame Noor
University, PO Box 19395-3697,
Tehran, Iran
In this research, a novel organic–inorganic hybrid salt, namely, N1,N1,N2,N2-tet-
ramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium tetrachloroferrate ([TMBSED]
[FeCl4]2) was prepared and characterized by Fourier-transform infrared spec-
troscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), elemental map-
ping, field emission scanning electron microscopy (FE-SEM), X-ray diffraction
(XRD), thermal gravimetric (TG), differential thermal gravimetric (DTG), and
vibrating-sample magnetometry (VSM) analyses. Catalytic activity of the hybrid
salt was tested for the synthesis of N,N0-alkylidene bisamides through the reac-
tion of benzamide (2 eq.) and aromatic aldehydes (1 eq.) under solvent-free con-
ditions in which the products were obtained in high yields and short reaction
times. The catalyst was superior to many of the reported catalysts in terms of
two or more of these factors: the reaction medium and temperature, yield, time,
and turnover frequency (TOF). [TMBSED][FeCl4]2 is a Brønsted–Lewis acidic
catalyst; there are two SO3H groups (as Brønsted acidic sites) and two
tetrachloroferrate anions (as Lewis acidic sites) in its structure. Highly effective-
ness of the catalyst for the synthesis of N,N0-alkylidene bisamides can be attrib-
uted to synergy of the Brønsted and Lewis acids and also possessing two sites of
each acid.
Correspondence
Abdolkarim Zare and Seyed Sajad
Sajadikhah, Department of Chemistry,
Payame Noor University, PO Box
19395-3697, Tehran, Iran.
Email: abdolkarimzare@pnu.ac.ir;
abdolkarimzare@yahoo.com;
sssajadi@pnu.ac.ir
Funding information
Research Council of Payame Noor
University
K E Y W O R D S
Brønsted–Lewis acidic catalyst, N,N0-alkylidene bisamide, N1,N1,N2,N2-tetramethyl-N1,N2-bis
(sulfo)ethane-1,2-diaminium tetrachloroferrate ([TMBSED][FeCl4]2), organic–inorganic hybrid
salt, solvent-free
1 | INTRODUCTION
worth note that characteristics of the hybrid materials are
not only sum of their organic and inorganic constituents
Organic–inorganic hybrid material is generally defined as
a compound in which the structure is formed from
organic and inorganic components interacting with each
other at the molecular scale. This can be occurred by
weak interactions such as hydrogen bonding, van der
Waals forces, and electrostatic interactions or through
strong coordinative, covalent, and ionic bonds.[1] It is
properties but also related to the nature of the interfaces
and the ratio of each moiety.[2] A significant class of these
compounds involves organic–inorganic hybrid salts.[3]
The hybrid materials have several unbeatable advantages,
consisting of eco-friendly nature, designable for a variety
of applications, effectiveness, appropriate thermal and
chemical stability, noncorrosiveness, and simple isolation
Appl Organomet Chem. 2020;e6046.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.6046

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ZARE ET AL.
from the process reactor. They have various applications
in pharmaceutical and industrial fields; for example, they
have been applied as semiconductor,[4] sensors,[5] and
photodetector[6] and in fluid–fluid separations,[7] cancer
therapy,[8] luminescence studies,[9] and optical
devices.[10] Organic–inorganic hybrid materials have
been also employed as efficient catalysts in synthetic
organic chemistry.[11–19]
X-ray diffraction (XRD), thermal gravimetric (TG), differ-
ential thermal gravimetric (DTG), and vibrating-sample
magnetometry (VSM) analyses. Then, it has been used
as a highly effectual Brønsted–Lewis acidic catalyst
for the preparation of N,N0-alkylidene bisamides
through the reaction of benzamide (2 eq.) with aro-
matic aldehydes (1 eq.) under solvent-free and green
conditions.
Bisamide functional group can be found in the scaf-
fold of a wide range of biologically, pharmaceutically,
and industrially important compounds.[20–31] Bisamides
have been used as ligands for the preparation of biologi-
cally active compounds in the Ullmann reaction[20] and
as essential moieties to introduce gem-diaminoalkyl
groups in retro-inverse pseudo-peptide materials.[21]
These compounds have been utilized in the synthesis of
peptidomimetic compounds.[22] Bisamide-containing
compounds have been also applied as drug release,[23]
antitumor,[24] anti-inflammatory,[25] and antimicrobial[25]
agents. Moreover, bisamides coordinated with metal ions
have been utilized for bimodal (optical/magnetic reso-
nance) imaging,[26] magnetic resonance imaging (MRI)
blood-pool contrasting,[27] and removal of organic
dyes[28] and as inhibitor against α-glucosidase[29] and
reagents in organic synthesis.[30,31] A kind of these com-
pounds is N,N0-alkylidene bisamides, which has been
synthesized through the reaction of primary amides
(2 eq.) and aldehydes (1 eq.); some catalysts have been
reported to perform this transformation, for example,
KH2PO4 supported on silica from rice husk ash
(H2PO4@RHA),[32] H14[NaP5W29MoO110],[33] sulfonated
2 | EXPERIMENTAL SECTION
2.1 | Materials and instruments
All reactants and solvents were purchased from Merck
or Fluka Chemical Companies. Identification of the
known products was done by comparing their melting
points and/or spectral data with the reported data.
Observing the reactions progress was achieved by thin-
layer chromatography (TLC) using silica gel SIL G/UV
254 plates. The nuclear magnetic resonance (NMR)
spectra were run on a Bruker Avance DPX FT-NMR
spectrometer (δ in ppm). Melting points were
measured on a Buchi B-545 instrument in open capil-
lary tubes. FT-IR spectrums were recorded by
a
Shimadzu IR-60 instrument. EDX and mapping analy-
sis were done by a SAMX-EDS apparatus (France sys-
tem). The morphologies and sizes of the particles were
characterized by FE-SEM, model MIRA3TESCAN-
XMU. The XRD analysis was carried out using a
device model: X'Pert PRO MPD, PANalytical, the Neth-
erlands (Cu Kα radiation, λ = 1.5408). Thermal gravi-
metric analysis (TGA) was performed by a Bahr STA
504 instrument (Germany), at 25–600ꢀC, with
temperature increment rate of 10ꢀC min−1 in argon
atmosphere.
carbon/nano-titania
composite
(C/TiO2-SO3H),[34]
hydroxyapatite,[35] ZnO/KIT-6@NiFe2O4,[36] nano-2-[N0,-
N0-dimethyl-N0-(silica-n-propyl)ethanaminium chloride]-
N,N-dimethylaminium
bisulfate
(nano-[DSPECDA]
[HSO4]),[37] montmorillonite K10,[38] NiFe2O4@SiO2-
PPA,[39] 3D-network polymer-supported ionic liquid,[40]
molybdate sulfuric acid (MSA),[40] silica sulfuric acid
(SSA),[41] and graphene oxide anchored with sulfonic
acid-functionalized glycerin (GO@Gl-SO3H).[42]
2.2 | The synthesis of [TMBSED][FeCl4]2
Solvent-free condition is a practical, well-known,
useful, and green technique that has been used in organic
synthesis; its advantages have been mentioned in the
literature.[43–45]
Considering the high significance of organic–
inorganic hybrid materials and N,N0-alkylidene
bisamides, herein, a novel organic–inorganic hybrid salt,
namely, N1,N1,N2,N2-tetramethyl-N1,N2-bis(sulfo)ethane-
1,2-diaminium tetrachloroferrate ([TMBSED][FeCl4]2)
has been synthesized and characterized by Fourier-
transform infrared spectroscopy (FT-IR), energy-
dispersive X-ray spectroscopy (EDX), elemental mapping,
field emission scanning electron microscopy (FE-SEM),
A solution of N1,N1,N2,N2-tetramethylethane-1,2-diamine
(5 mmol, 0.581 g) in dry CH2Cl2 (20 mL) was added
dropwise to a stirring solution of chlorosulfonic acid
(10 mmol, 1.165 g) in dry CH2Cl2 (20 mL) over a period
of 10 min, at 10ꢀC, and the resulting solution was stirred
for 4 h at room temperature. Afterward, the solvent was
evaporated; the liquid residue was triturated with dry
petroleum ether (3 × 2 mL) and dried under vacuum at
90ꢀC to produce [TMBSED][Cl]2.[46,47] Finally, FeCl3
(10 mmol, 1.622 g) was gradually added to [TMBSED]
[Cl]2 (5 mmol, 1.746 g) and stirred for 2 h at room tem-
perature and 12 h at 70ꢀC to afford [TMBSED][FeCl4]2
(Scheme 1).

ZARE ET AL.
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SCHEME 1 The synthesis of
[TMBSED][FeCl4]2
FIGURE 1 The FT-IR spectrum of [TMBSED][FeCl4]2
2.3 | General procedure for the
Note: Selected spectral data and original spectrums of
the synthesized bisamides have been presented in
supporting information (Figures S1–S6).
preparation of N,N0-alkylidene bisamides
A mixture of banzamide (2 mmol, 0.242 g), aldehyde
(1 mmol), and [TMBSED][FeCl4]2 (0.1 mmol, 0.067 g)
was strongly stirred by a small rod at 80ꢀC. When TLC
showed consuming the reactants, the reaction mixture
was cooled to room temperature; EtOAc (10 mL) was
added and stirred for 2 min under reflux conditions; the
insoluble catalyst was isolated by centrifuging and
decanting (the catalyst was washed by EtOAc [2 × 3 mL]
and dried). The EtOAc obtained from the decanting was
distilled, and the remainder solid was recrystallized from
EtOH (95%) to give the pure product. [TMBSED][FeCl4]2
was reusable for one time.
3 | RESULTS AND DISCUSSION
3.1 | The catalyst characterization
The novel organic–inorganic hybrid salt, N1,N1,N2,N2-
tetramethyl-N1,N2-bis
(sulfo)ethane-1,2-diaminium
tetrachloroferrate ([TMBSED][FeCl4]2), was character-
ized by FT-IR, EDX, elemental mapping, FE-SEM, XRD,
TG, DTG, and VSM techniques.
TABLE 1 The FT-IR data of [TMBSED][FeCl4]2
Adsorption (cm−1
)
Bond or functional group
Stretching of OH groups of SO3H
Bending of C–H
ꢁ3,650–2,000
1,460
1,252
1,103
721
Stretching of C–N
Symmetric stretching of –SO2–
Symmetric of S–O
585
Bending of –SO2–
373
Fe–Cl of tetrachloroferrate
Fe–Cl of tetrachloroferrate
Cl–Fe–Cl of tetrachloroferrate
283
123
Abbreviation: FT-IR, Fourier-transform infrared spectroscopy.
FIGURE 2 The EDX spectrum of [TMBSED][FeCl4]2

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FIGURE 3 Elemental mapping
analysis of the catalyst

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The FT-IR spectrum of [TMBSED][FeCl4]2 is presented
in Figure 1, and the related adsorptions to each bond and
functional group are shown in Table 1. The peaks cor-
responded to all expected bonds or functional groups in
the cation and anion of the hybrid salt were observed in
the spectrum. The interpretation of the FT-IR spectral data
is in accordance with the literature data.[12,46–49]
Existing all expected elements (C, O, N, S, Fe, and Cl)
in the structure of the organic–inorganic hybrid material
were verified by EDX; no extra element was observed in
the spectrum (Figure 2). Presence of carbon, oxygen,
nitrogen, sulfur, iron, and chlorine elements in the struc-
ture of [TMBSED][FeCl4]2 was also confirmed by ele-
mental mapping analysis, as shown in Figure 3.
The FE-SEM images of [TMBSED][FeCl4]2 are illus-
trated in Figure 4. As it can be seen in Figure 3, most of
the particles sizes were micro (105–171 nm), and a few of
them were nano (86–96 nm).
The XRD pattern of the catalyst (Figure 5) indicated
several sharp peaks at 2θ ≈ 8.8, 9.8, 13.4, 16.0, 17.2, 18.9,
21.3, 22.0, 25.2, 26.9, 28.8, 30.5, 38.6, 39.5, 43.2, 44.9 and a
few broad peaks (relatively) at 2θ ≈ 50.7–53.0, 53.0–55.0,
57.6–60.2ꢀ. According to these results, most of the parti-
cles have crystalline form, and some of them have
amosphorous form. The chemical sources confirmed
these interpratations.[12,19]
Thermal stability of [TMBSED][FeCl4]2 was deter-
mined by TGA. Considering the TG diagram (Figure 6),
the organic–inorganic hybrid salt showed proper thermal
stability, and main weight losses (decomposition) were
occurred after about 205ꢀC. Thus, it can be utilized as
catalyst for organic transformations that need high tem-
perature to perform. The weight losses were occurred in
three steps. The first weight loss (ꢁ11.5%) below about
172ꢀC (with Tmax at 121ꢀC in DTG plot) can be attributed
to evaporation of adsorbed water and other solvents by
[TMBSED][FeCl4]2. The second and third weight losses
(ꢁ56%) were happened at about 172–425ꢀC (with Tmax at
242ꢀC in DTG plot) and 425–550ꢀC (with Tmax at 507ꢀC
in DTG plot), respectively, and may be due to loss of SO3,
NHMe2, and CH2 CH2 from the organic moiety, conver-
sion of tetrachloroferrate to ferric chloride, and oxidation
of tetrachloroferrate by oxygen of SO3. The interpreta-
tions were achieved considering the literature.[11,12,50–52]
Magnetic property of N1,N1,N2,N2-tetramethyl-N1,N2-
bis(sulfo)ethane-1,2-diaminium tetrachloroferrate was
determined by a vibrating sample magnetometer at room
temperature; the VSM plot is demonstrated in Figure 7.
A linear plot was observed for our catalyst, indicating the
paramagnetic property (a paramagnetic material is
weakly attracted by an external magnetic field and forms
internal induced magnetic fields in the direction of the
external applied magnetic field).[50,53]
FIGURE 4 The FE-SEM images of [TMBSED][FeCl4]2
3.2 | Catalytic activity of [TMEDSA]
[FeCl4]2
Catalytic activity of [TMBSED][FeCl4]2 was investigated
for the synthesis of N,N0-alkylidene bisamides. To find
the optimal reaction conditions, the condensation of ban-
zamide (2 mmol) and 3-nitrobanzaldehyde (1 mmol) was

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ZARE ET AL.
FIGURE 5 The XRD pattern of [TMBSED]
[FeCl4]2
were obtained at 80ꢀC using 10 mol% of the catalyst (the
reaction time: 10 min; yield: 96%). Increasing the catalyst
amount up to 12 mol% and the temperature up to 90ꢀC
has no significant effect on the reaction time and yield.
To determine generality and effectiveness of
[TMBSED][FeCl4]2 in the preparation of N,N0-alkylidene
bisamides, the condensation of benzamide with different
aromatic aldehydes (containing electron-withdrawing,
electron-donating, and halogen groups) was examined
under the optimal conditions. The obtained reaction
times, yields, and turnover frequencies (TOFs) are repre-
sented in Table 2. In all cases, the corresponding N,N0-
alkylidene bisamides were obtained in high yields, short
times, and good TOF. Additionally, all products were
cleanly purified by recrystallization from hot ethanol
(95%) and without use of column chromatography.
FIGURE 6 The TG and DTG diagrams of [TMBSED][FeCl4]2
Considering the literature[32,37,54] and Brønsted–Lewis
acidity of [TMBSED][FeCl4]2, a plausible mechanism was
proposed for the preparation of N,N0-alkylidene
bisamides (Scheme 3). At first, carbonyl group of the
aldehyde is activated by the Brønsted and Lewis acidic
moieties of the catalyst (SO3H and tetrachloroferrate)
and then NH2 group of benzamide performed a nucleo-
philic attack to the activated carbonyl to provide interme-
diate I. The Brønsted and Lewis acidic sites of the hybrid
material accelerate removing a H2O molecule from I to
obtain intermediate II. Michael-type addition of
benzamide to the activated II (by the SO3H and
tetrachloroferrate groups of the catalyst) gives III.
Tautomerization of intermediate III by aid of [TMBSED]
[FeCl4]2 produces the bisamide. Lewis acidity of
tetrachloroferrate-bearing catalysts has been mentioned
in the literature.[54] The highly effectuality of [TMBSED]
[FeCl4]2 can be related to its Brønsted–Lewis acidic prop-
erty (which all steps of the reaction catalyze by both
Brønsted and Lewis acidic sites) and also possessing two
sites of each acid.
FIGURE 7 The VSM diagram of the hybrid salt
chosen as a model reaction (Scheme 2). The reaction was
examined in the presence of different amounts of
[TMBSED][FeCl4]2 (5–12 mol%) at a temperature range
of 70–90ꢀC under solvent-free conditions. The best results

ZARE ET AL.
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SCHEME 2 The model reaction for optimization of conditions
TABLE 2 The production of N,N0-alkylidene bisamide derivatives using [TMBSED][FeCl4]2
Product
3a
Ar
Time (min)
Yielda (%)
TOF (min−1
0.47
)
M.p. ꢀC, measured (reported)
C6H5
20
20
10
25
25
20
15
25
10
15
20
20
94
92
96
90
89
93
92
96
93
97
95
94
216–218 (218–219)[32]
261–263 (259–261)[37]
228–230 (228–230)[32]
252–254 (255–257)[37]
224–226 (223–225)[37]
190–192 (193–195)[32]
237–239 (240–241)[32]
206–208 (207–209)[38]
255–257 (256–258)[32]
256–258 (252–254)[33]
239–241 (241–242)[36]
194–196 (192–194)[32]
3b
4-O2NC6H4
3-O2NC6H4
2-O2NC6H4
4-MeOC6H4
3-MeOC6H4
4-MeC6H4
4-FC6H4
0.46
3c
0.96
3d
3e
0.36
0.36
3f
0.47
3g
0.61
3h
3i
0.38
4-BrC6H4
4-ClC6H4
2-ClC6H4
2,4-Cl2C6H3
0.93
3j
0.65
3k
3l
0.48
0.47
aIsolated yield (most of the reactions were completed; that is, all the reactants were consumed, and only one desired product was obtained).
Abbreviation: TOF, turnover frequency.
SCHEME 3 The proposed
mechanism for the production of
N,N0-alkylidene bisamides
In another study, the results and reaction condi-
tions of [TMBSED][FeCl4]2 for the production of N,N0-
alkylidene bisamides were compared with those of the
reported catalysts (Table 3). As the data of Table 3
illustrate, [TMBSED][FeCl4]2 was superior with the
other catalysts in terms of two or more of these

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ZARE ET AL.
TABLE 3 Comparing the reaction conditions and the results of [TMBSED][FeCl4]2 with those in the reported catalysts for the
production of N,N0-alkylidene bisamides
Catalyst
Conditions
Time (min)
10–25
15
Yield (%)
89–97
71–96
74–95
85–94
87–95
75–97
79–98
71–85
52–93
79–92
TOF (min−1
)
Ref.
[TMBSED][FeCl4]2
H2PO4@RHA
Solvent-free, 80ꢀC
Solvent-free, 80ꢀC
MeOH, reflux
0.36–0.96
This work
a
–
Saadati-Moshtaghin[32]
Maleki et al.[33]
Kour and Paul[34]
Ramachandran et al.[35]
Saadati-Moshtaghin et al.[36]
Zare et al.[37]
Lambat et al.[38]
Maleki and Baghayeri[39]
Mouradzadegun et al.[40]
H14[NaP5W29MoO110
C/TiO2-SO3H
]
50–150
30–180
180
0.56–3.80
0.08–0.44
0.10–0.11
Solvent-free, 100ꢀC
Hydroxyapatite
MeOH, reflux
a
NiFe2O4@KIT-6@ZnO
Nano-[DSPECDA][HSO4]
Montmorillonite K10
NiFe2O4@SiO2-PPA
Solvent-free, 60ꢀC
Solvent-free, 90ꢀC
Solvent-free, 100ꢀC
MeOH, reflux
10
–
15–30
27–180
40–130
20–50
1.20–2.97
a
–
a
–
Polymer-supported
Toluene, reflux
0.22–0.46
Brønsted acid ionic liquid
MSA
EtOAc, 80–90ꢀC
EtOAc, 80–90ꢀC
Solvent-free, 110ꢀC
25–40
25–45
10–25
85–91
85–90
88–96
0.22–0.36
Tamaddon et al.[41]
Tamaddon et al.[41]
Naeim-Fallahiyeh et al.[42]
a
SSA
–
a
GO@Gl-SO3H
–
aIn this research, amount of the active site of the catalyst has not been determined; thus, it was not possible to calculate TOF.
Abbreviation: TOF, turnover frequency.
factors: the reaction medium (performing the synthesis
under solvent-free conditions or in toxic solvents), tem-
perature, yield, time, and TOF.
methodology; software. Seyed Sajad Sajadikhah: Inves-
tigation; project administration; supervision.
CONFLICT OF INTEREST
There are no conflicts to declare.
4 | CONCLUSIONS
DATA AVAILABILITY STATEMENT
All data have been given in the article and supporting
information.
Briefly, a novel organic–inorganic hybrid salt was
introduced as
a
Brønsted–Lewis acid catalyst
for organic synthesis; N1,N1,N2,N2-tetramethyl-N1,N2-bis
(sulfo)ethane-1,2-diaminium tetrachloroferrate can cata-
lyze organic reactions that require acidic catalysts. In
this study, the synthesis of N,N0-alkylidene bisamides
has successfully catalyzed by the hybrid salt; this syn-
thesis has the following advantages: effectuality, gener-
ality, application of solvent-free conditions, high yields,
short reaction times, goot TOF, simplicity (procedure,
workup, and purification of the products), good agree-
ment with green chemistry principles, usage of a Brøn-
sted–Lewis acid catalyst, easy preparation of the
catalyst, and superiority of [TMBSED][FeCl4]2 relative
to many reported catalysts.
ORCID
Abdolkarim Zare https://orcid.org/0000-0002-8210-
3155
Fatemeh Monfared https://orcid.org/0000-0002-9979-
3498
Seyed Sajad Sajadikhah https://orcid.org/0000-0002-
4415-5325
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supervision. Fatemeh
Monfared:
Investigation;

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How to cite this article: Zare A, Monfared F,
Sajadikhah SS. Synthesis and characterization of a
novel organic–inorganic hybrid salt and its
application as a highly effectual Brønsted–Lewis
acidic catalyst for the production of N,N0-
alkylidene bisamides. Appl Organomet Chem. 2020;
e6046. https://doi.org/10.1002/aoc.6046