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Sana Bougueroua

Ylène Aboulfath

Alvaro Cimas

Ali Hashemi

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Marie-Pierre Gaigeot

Topological graphs: a review of some of our achievements and perspectives in physical chemistry and homogeneous catalysis

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Comptes Rendus
Chimie
Selma Mestour, Abdeslam-Hassen Meniai, Sarra Melloul and Mehdi Louaer
Addendum: Sustainability by extraction of bioactive compounds from onion seeds
Volume 27, Special Issue S3 (2024), p. 69
Part of Special Issue: Materials and Energy Valorization of Biomass and Waste: The
Path for Sustainability and Circular Economy Promotion
Guest editors: Mejdi Jeguirim (Université de Haute-Alsace, Institut de Sciences des
Matériaux de Mulhouse, France) and Salah Jellali (Sultan Qaboos University, Oman)
https://doi.org/10.5802/crchim.384
This article is licensed under the
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C EN T R E
MER S ENN E
The Comptes Rendus. Chimie are a member of the
Mersenne Center for open scientific publishing
www.centre-mersenne.org — e-ISSN : 1878-1543
Comptes Rendus. Chimie
2024, Vol. 27, Special issue S3, p. 69
https://doi.org/10.5802/crchim.384
Erratum
Materials and Energy Valorization of Biomass and Waste: The Path for
Sustainability and Circular Economy Promotion
Addendum: Sustainability by extraction of bioactive
compounds from onion seeds
SelmaMestour a, Abdeslam-HassenMeniai ,∗,a, Sarra Melloul a andMehdi Louaer a
a Laboratoire de l’Ingénierie des Procédés de l’Environnement, Université
Constantine 3, Algeria
E-mail: meniai@yahoo.fr (A.-H. Meniai)
Manuscript received 6 December 2024, accepted 11 February 2025.
This note provides a complement to the article in
Comptes Rendus. Chimie bearing the above title. The
concerned article was published online on May 14,
2024, in Volume 27(S3), 2024, pages 1–13, https://doi.
org/10.5802/crchim.303.
In order to correct an omission, acknowledgments
are addressed to the Algerian General Agency of
Scientific Research and Technological Development
(DGRSDT) the funder of the Im-pack project in the
frame of the European Union supported PRIMA pro-
gram, and the following text is inserted at the end of
the article.
The authors apologize for any inconvenience.
∗Corresponding author
ISSN (electronic): 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/


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Ashutosh Patel

Raman Deep

Shivam Gautam

Performance augmentation of triangular solar still using sensible energy storage materials: thermo-exergo-economic and sustainability analyses

Simon Pascal

Elena Zaborova

Olivier Siri

Comptes Rendus
Chimie
Simon Pascal, Elena Zaborova and Olivier Siri
1,2,4-Triamino-5-nitrobenzene as air-stable aromatic polyamines for coordination
chemistry
Volume 27, Special Issue S1 (2024), p. 69-75
Online since: 23 August 2024
Issue date: 24 December 2024
Part of Special Issue: French/Nordic Special Issue on Materials and Coordination
Chemistry
Guest editors: Claude P. Gros (Université de Bourgogne, Dijon, France) and Abhik
Ghosh (The Arctic University, UiT, Tromsø, Norway)
https://doi.org/10.5802/crchim.292
This article is licensed under the
Creative Commons Attribution 4.0 International License.
http://creativecommons.org/licenses/by/4.0/
C EN T R E
MER S ENN E
The Comptes Rendus. Chimie are a member of the
Mersenne Center for open scientific publishing
www.centre-mersenne.org — e-ISSN : 1878-1543
Comptes Rendus. Chimie
2024, Vol. 27, Special issue S1, p. 69-75
https://doi.org/10.5802/crchim.292
Research article
French/Nordic Special Issue on Materials and Coordination Chemistry
1,2,4-Triamino-5-nitrobenzene as air-stable
aromatic polyamines for coordination chemistry
Simon Pascal ,∗,a,b, Elena Zaborova ,a and Olivier Siri ,∗,a
a Aix-Marseille Univ, Centre Interdisciplinaire de Nanoscience de Marseille (CINaM),
CNRS UMR 7325, Campus de Luminy, case 913, Marseille cedex 09 13288, France
b Nantes Université, CNRS, CEISAM, UMR 6230, Nantes, F-44000, France
E-mails: simon.pascal@cnrs.fr (S. Pascal), olivier.siri@univ-amu.fr (O. Siri)
Abstract. We report the synthesis and characterization of two nickel complexes 7 and 8 based on
1,2,4-triamino-5-nitrobenzene 6. The formation of these compounds is observed from the same
precursor, their stoichiometry depending on the nature of the solvent used for the crystallization.
The key role of the nitro group in 6 is discussed, demonstrating its major impact on the stability
and reactivity of the ligand. Each nickel complex could be characterized by single crystal X-ray
analysis, highlighting the importance of the intramolecular H-bonding interactions on the stability
of the complexes incorporating a monodentate aromatic amine-type ligand.
Keywords. Aromatic amines, Acac ligand, Metal coordination, X-ray structure, Nickel complexes.
Funding. CNRS, French “Ministère de la Recherche et de l’Enseignement Supérieur”.
Manuscript received 31 August 2023, revised 9 November 2023, accepted 24 January 2024.
1. Introduction
Phenylenediamine derivatives 1–3 (Figure 1) are an
important class of organic compounds with rich
chemical and physical properties [1–3] and remark-
able applications as precursors in color chemistry [4,
5]. Their coordinating ability has been less investi-
gated because phenylenediamines do not form very
stable complexes with bivalent metal ions [6]. This
poor stability can be explained by the low basicity of
the aromatic amines due to the delocalization of the
lone pair of the nitrogen atom toward the p orbitals of
the aromatic ring, decreasing the electron density on
the nitrogen atom available for the bond formation
with a metal center. The coordinating ability of aro-
∗Corresponding authors
matic diamines is also conditioned by the position
of the nitrogen atoms on the aromatic ring (ortho,
meta or para). o-Phenylenediamine ligand 1 coor-
dinates either in a monodentate, chelating bidentate
and bridging bidentate fashion in different dinuclear
complexes, with possible oxidation of 1 depending
on the metal center [7]. Studies of coordination com-
pounds of 2 and 3 in solution and solid state are rare,
possibly because these ligands can only coordinate
one nitrogen atom to a metal center by means of a
weak linkage [7], but also because of oxidation pro-
cesses forming p-benzoquinonediimine ligands [8].
Falthouse and Hendrickson have reported a series of
binuclear Cu(II) complexes in which 2 acts as a bridg-
ing bidentate ligand but the instability inherent to the
phenylenediamines made it difficult to fully charac-
terize the complexes [9].
ISSN (electronic): 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/
70 Simon Pascal et al.
Figure 1. Molecules studies in previous works
and our work.
As an extension of these studies, it appeared very
attractive to investigate 1,2,4-triaminobenzene 4,
which combines the structural elements of 1, 2
and 3, as ligand in coordination chemistry. However,
bearing three amino functions, molecule 4 is highly
unstable in air and can be easily oxidized, sacrificing
its aromatic character in favor of a quinoidal form.
To overcome this limitation, we envisaged the use
of analogs of type 5 because the incorporation of an
electron-withdrawing nitro group should strongly re-
duce the electron density and consequently prevent
air oxidation of the molecule.
Herein, we wish to describe the synthesis and
X-ray diffraction analysis of two new complexes
(7 and 8), based on the air-stable 1,2,4-triamino-5-
nitrobenzene derivative 6. Importantly, the key role
of the nitro group on the stability and the reactivity of
the ligand is clearly emphasized, illustrating a further
aspect to be considered in the coordination chem-
istry of aromatic amines.
2. Results and discussion
Precursor 6 was first prepared as recently reported in
the literature [10]. Its metalation with Ni(acac)2 in
toluene at room temperature led to the formation of a
beige precipitate (BP) that could be isolated by filtra-
tion (Scheme 1). IR analysis of this powder compared
to the precursor 6 (Figure 2) revealed the appearance
of strong bands around 1380, 1020 and 925 cm−1,
Figure 2. IR spectra of precursor 6 (black) and
BP (red).
which could be attributed to carbon–oxygen and
carbon–carbon bonds. In addition, the N–H vi-
brations above 3250 cm−1 for 6 are shifted for BP
whereas the C–H vibrations (2900 cm−1) are not af-
fected. These observations are consistent with the
coordination of one or several NH2 group(s) to the
nickel center and the presence of acetylacetonate
(acac) moieties as ancillary ligand.
Next, we characterized BP in solution. Its 1H NMR
spectra in acetone-d6 and methanol-d4 are reported
in Figure 3, showing signals of aliphatic chains of lig-
and 6 and peaks of the acac moiety in the 1–5 ppm
region, together with the presence of square pla-
nar low-spin complexes (i.e., diamagnetic character).
Unfortunately, further investigations by mass spec-
trometry could not afford usable data due to the pres-
ence of numerous peaks in both methanol and ace-
tone solutions.
Interestingly, the UV–Vis spectroscopic data
recorded in methanol and acetone revealed the same
absorption profile for BP and 6 (Figure 4). This ob-
servation proved the instability of the complex BP in
solution by means of a weak linkage, suggesting that
6 probably coordinates only one nitrogen atom to a
metal center (unlike 1) [7]. Crystallization attempts
of BP in different solvents were then performed to
gain insights into the nature of the coordination
mode of 6.
Single crystals suitable for structural determina-
tion could be obtained by slow evaporation of a
Simon Pascal et al. 71
Figure 3. 1H NMR (400 MHz) spectrum of 6 in acetone-d6 (top) and BP in acetone-d6 (middle) or
methanol-d4 (bottom). The solvent’s residual peak is indicated with an asterisk.
72 Simon Pascal et al.
Scheme 1. Synthesis of complexes 7 and 8 (acac = acetylacetonate).
solution of BP in methanol. The X-ray diffrac-
tion analysis revealed the formation of a 1:2 (metal
(Ni)/ligand (6)) complex 7 in which the nickel ion
is found in an octahedral geometry and surrounded
by two acac moieties coordinated in a planar fashion
with respect to the metal center (Figure 5).
The Ni coordination sphere is completed by two
additional ligands 6 in which a single amino group
N(1) (and N′(1)) is coordinated. The monoden-
tate coordination mode of 6 can be explained by a
closer look at its molecular structure. Since only
the amine function N(1) in meta position is not con-
jugated with the nitro group, it coordinates specif-
ically with a metal center due to the availability of
its lone pair, in contrast to the two other amine
functions in para and ortho positions, which are
highly conjugated with the nitro group. This hy-
pothesis is confirmed experimentally by examination
of the bond lengths between the nitrogen atoms of
the amines and their corresponding aromatic car-
bons. The distance N(1)· · ·C(Ar) of 1.437 Å clearly
indicates a lack of conjugation and availability of
Simon Pascal et al. 73
Figure 4. UV–visible absorption spectra of 6
and BP dissolved in acetone (top) or methanol
(bottom).
the lone pair whereas the distances N(4)· · ·C(Ar) and
N(3)· · ·C(Ar) are much shorter due to the conjuga-
tion with NO2 (1.355 and 1.350 Å, respectively). A
close examination of the hydrogen-bonding inter-
actions in 7 revealed H-bonds involving N(1), N(2)
and N(3) (as H-donor or H-acceptor) that clearly sta-
bilize the molecular architecture in the solid state
(Figure 5).
Remarkably, we observed that recrystallisation of
BP in acetone instead of methanol led to the forma-
tion of complex 8 having the same octahedral ge-
ometry but a different stoichiometry (2:2 versus 1:2)
(Figure 6). By analogy with 7, ligand 6 is monodentate
since only the amine function N(1), in meta po-
sition with respect to the nitro group, is coordi-
nated to the Ni center owing to the availability of
its lone pair. Numerous N–H· · ·O bonding interac-
tions involving N(1), N(2) and N(3), ranging from
1.976 to 2.251 Å, contribute to the stabilization of the
complex.
The most striking feature of 8 is the coordi-
nation mode adopted by two of the six acac lig-
ands, one of whose oxygen atoms coordinates to
two metal centers, acting as a bridging ligand (Fig-
ure 6). As a result, the two Ni centers are in proxim-
ity (d(Ni· · ·Ni) = 3.215 Å). To the best of our knowl-
edge, this arrangement was only observed for modi-
fied acac in which electron-donating substituents in
the 3-position of the pentane-2,4-dionato group were
added [11].
3. Experimental section
3.1. General
Solvents (HPLC grade) and reagents were purchased
from Sigma Aldrich and were used as received.
Compound 6 was prepared according to published
procedures [10]. NMR spectra were recorded on
a JEOL ECS400 NMR spectrometer at room tem-
perature. IR spectra were recorded on an Agilent
Cary 630 FTIR equipped with an attenuated total
reflectance (ATR) sampling. Suitable crystals were
mounted on a Rigaku Oxford Diffraction SuperNova
diffractometer and measured at 293 K at the Cu
radiation (λ = 1.54184 Å). Data collection, reduc-
tion and multiscan ABSPACK correction were per-
formed with CrysAlisPro (Rigaku Oxford Diffraction).
Using Olex2, the structures were solved with the
ShelXT structure solution program using Intrinsic
Phasing and refined with ShelXL using least-square
minimization.
3.2. Synthesis of BP
Ni(acac)2 (m = 204 g, 0.792 mmol, 2 equiv) was added
to an orange–red solution of 6 (100 mg, 0.396 mmol,
1 equiv) in 20 ml of toluene under vigorous stir-
ring. The reaction mixture was stirred at room
temperature for 4 h. The precipitate obtained was
then isolated by filtration on a sintered glass fun-
nel and dried in vacuo to afford BP as a beige solid
(m = 184 mg).
74 Simon Pascal et al.
Figure 5. Single-crystal X-ray structure of 7 (recrystallization of BP in methanol). Selected bond lengths
are indicated in Å.
Figure 6. Single-crystal X-ray structure of 8 (recrystallization of BP in acetone). For the ortep view on the
right, the aromatic amino ligand 6 is omitted for clarity except for the amino function coordinated to the
Ni center. Selected bond lengths are indicated in Å.
4. Conclusion
We have prepared and crystallized novel nickel com-
plexes 7 and 8 incorporating a new aromatic triamino
ligand 6. This ligand behaves in a monodentate fash-
ion in coordination chemistry because of the pres-
ence of the electron-withdrawing group NO2 that
“deactivates” the two amine functions in ortho and
para position. Although scarce in the literature due
to a weak linkage inherent to the monodentate aro-
matic amines, complexes 7 and 8 could be fully char-
acterized by X-ray diffraction, probably because of
the presence of numerous intramolecular H-bonding
interactions. The structure determination clearly es-
tablished two different metal (Ni)/ligand (6) stoi-
chiometry depending on the solvent used for crys-
tallization, and the formation of a 1:2 complex (7)
or a 2:2 adduct (8) could be observed in methanol
Simon Pascal et al. 75
and acetone, respectively. This work might open new
perspectives in coordination chemistry of aromatic
polyamines by exploiting the NH2/NO2 balance to
tune the reactivity of the ligand and/or the stability
of the metal complexes.
Declaration of interests
The authors do not work for, advise, own shares in,
or receive funds from any organization that could
benefit from this article, and have declared no affil-
iations other than their research organizations.
Funding
This work was supported by the CNRS and the French
“Ministère de la Recherche et de l’Enseignement
Supérieur.”
Acknowledgements
The authors thank M. Giorgi (Spectropole, Marseille)
for the X-ray diffraction studies.
Supplementary data
Supporting information for this article is available on
the journal’s website under https://doi.org/10.5802/
crchim.292 or from the author.
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1,2,4-Triamino-5-nitrobenzene as air-stable aromatic polyamines for coordination chemistry

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S1 
Supporting Information for 
Assessment of the applied potential of sludge-derived hydrochar in terms 
of process parameters and product properties 
Chuang Zhang1, #, Bingyu Wang1, #, Jixiang Wang1, 2, Shaopeng Rong1, Huifang Xie1,* 
Hongxia Qu3, Yanfang Feng2 
1 Jiangsu Key Laboratory of Chemical Pollution Control and Resources Reuse, School of 
Environmental and Biological Engineering, Nanjing University of Science and Technology, 
Nanjing 210094, China 
2 Key Laboratory of Agro-Environment in Downstream of Yangtze Plain, National Agricultural 
Experiment Station for Agricultural Environment, Ministry of Agriculture and Rural Affairs, 
Institute of Agricultural Resources and Environment, Jiangsu Academy of Agricultural 
Sciences, Nanjing 210014, China 
3 School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 
210094, Jiangsu Province, China 
* Corresponding author: Dr. Huifang Xie, Email: huifangxie@njust.edu.cn
# These two authors contribute to this paper equally. 
 
S2 
 
Table S1 Basic properties of AS and DS. 
Samples 
Moisture 
(%) 
Ash 
(wt%, db) 
Elemental analysis (wt%, db)a HHVb 
(MJ/kg) 
R50 
C H O N S 
AS 98.4 46.9 26.8 4.4 16.8 4.6 0.5 11.87 0.45 
DS 80.3 48.2 25.4 4.5 17.3 4.2 0.5 11.37 0.44 
Samples 
Heavy metal (mg/g)c 
Zn Cu Ni Cr 
AS 0.2311 0.1422 0.0129 0.0025 
DS 0.1840 0.2158 0.0148 0.0086 
Note: 
a Determined by elemental analysis using the combustion method and O (Oxygen) was 
calculated by difference based on dry basis. 
b HHV, higher heating value and HHV=0.349C+1.1783H+0.1005S-0.1034O-0.0015N-
0.0211A. 
c Determined by ICP-OES. 
  
 
S3 
 
Table S2 Atomic ratio of AS-HCs and DS-HCs. 
Sample H/C O/C (O+N)/C C/N R50 HHV(MJ/kg) LHV(kJ/kg) 
AS 1.99 0.47 0.62 6.73 0.45 11.87 9.57 
AS-HC-180-1 2.23 0.47 0.59 8.57 0.38 8.85 7.08 
AS-HC-180-2 2.07 0.41 0.50 11.91 0.39 7.29 6.25 
AS-HC-180-3 2.10 0.39 0.47 11.86 0.39 7.73 6.46 
AS-HC-180-4 2.06 0.42 0.50 12.35 0.40 6.81 5.96 
AS-HC-220-1 2.11 0.42 0.51 11.70 0.40 6.93 5.95 
AS-HC-220-2 2.15 0.39 0.47 12.68 0.39 7.08 5.97 
AS-HC-220-3 1.97 0.30 0.36 15.83 0.42 6.79 5.92 
AS-HC-220-4 1.96 0.34 0.40 16.42 0.42 6.05 5.49 
AS-HC-260-1 2.01 0.35 0.42 15.74 0.42 5.98 5.40 
AS-HC-260-2 1.90 0.31 0.37 16.65 0.43 5.59 5.23 
AS-HC-260-3 1.88 0.29 0.35 17.15 0.44 5.97 5.50 
AS-HC-260-4 1.78 0.34 0.39 19.25 0.43 5.86 5.60 
DS 2.11 0.51 0.65 7.04 0.44 11.37 9.02 
DS-HC-180-1 2.04 0.48 0.60 8.28 0.39 11.62 9.32 
DS-HC-180-2 1.94 0.45 0.60 7.04 0.40 11.50 9.47 
DS-HC-180-3 1.85 0.37 0.48 9.14 0.40 9.33 7.96 
DS-HC-180-4 1.90 0.42 0.54 8.25 0.38 9.37 7.95 
DS-HC-220-1 2.00 0.45 0.58 7.58 0.40 11.06 8.94 
DS-HC-220-2 1.80 0.27 0.37 10.38 0.42 9.33 7.87 
DS-HC-220-3 1.79 0.33 0.42 10.70 0.41 8.99 7.75 
DS-HC-220-4 1.75 0.28 0.36 11.50 0.42 9.23 7.92 
DS-HC-260-1 1.79 0.27 0.36 10.86 0.41 9.14 7.77 
DS-HC-260-2 1.74 0.25 0.33 12.07 0.43 8.92 7.68 
DS-HC-260-3 1.67 0.20 0.28 13.24 0.44 8.60 7.50 
DS-HC-260-4 1.72 0.19 0.27 12.52 0.44 8.81 7.55 
Note: Atomic ratio is based on the elemental analysis result. The O/C: the atomic ratio of 
oxygen to carbon. (O+N)/C: the atomic ratio of the sum of nitrogen and oxygen to carbon. H/C: 
the atomic ratio of hydrogen to carbon. C/N: the atomic ratio of carbon to nitrogen. HHV: 
higher heating value; LHV: Lower heating value. 
  
 
S4 
 
Table S3 Parameters on process energy of DS-HCs. 
Parameters DS-180-2 DS-220-2 DS-260-4 
Vapor Pressure(Mpa) 1.0 2.3 4.7 
Vapor Density(kg/m3) 5.1 11.6 23.8 
Vapor Mass(kg) 16.1 36.3 74.6 
Required Energy(MJ) at 80.3% 2785 3530 4306 
Recovery Energy from HCs(MJ) 5337 5113 4308 
Note: Vapor Pressure= P(T); Vapor Mass=qs; Required Energy=Q. 
  
 
S5 
 
Table S4 The content of heavy metals in AS-HCs and DS-HCs. 
Sample Zn (mg/g) Cu (mg/g) Ni (mg/g) Cr (mg/g) 
AS 0.2311 0.1422 0.0129 0.0025 
AS-HC-180-1 0.4025 0.1010 0.0214 0.0143 
AS-HC-180-2 0.3320 0.0518 0.0192 0.0060 
AS-HC-180-3 0.6317 0.0716 0.0214 0.0112 
AS-HC-180-4 0.3673 0.1408 0.0211 0.0088 
AS-HC-220-1 0.4807 0.1080 0.0225 0.0171 
AS-HC-220-2 0.4764 0.1004 0.0205 0.0148 
AS-HC-220-3 0.5043 0.1346 0.0224 0.0151 
AS-HC-220-4 0.3548 0.0436 0.0184 0.0022 
AS-HC-260-1 0.4793 0.1554 0.0233 0.0201 
AS-HC-260-2 0.4838 0.1520 0.0199 0.0208 
AS-HC-260-3 0.5510 0.0997 0.0219 0.0175 
AS-HC-260-4 0.5019 0.1141 0.0253 0.0188 
DS 0.1840 0.2158 0.0148 0.0086 
DS-HC-180-1 0.2819 0.2526 0.0148 0.0042 
DS-HC-180-2 0.2757 0.1369 0.0142 0.0041 
DS-HC-180-3 0.2277 0.1467 0.0175 ND 
DS-HC-180-4 0.2830 0.0823 0.0164 0.0012 
DS-HC-220-1 0.2390 0.2125 0.0138 0.0095 
DS-HC-220-2 0.2576 0.1403 0.0172 0.0059 
DS-HC-220-3 0.3157 0.1747 0.0159 0.0051 
DS-HC-220-4 0.3013 0.2201 0.0171 0.0036 
DS-HC-260-1 0.2694 0.0985 0.0150 0.0011 
DS-HC-260-2 0.2970 0.1821 0.0192 0.0084 
DS-HC-260-3 0.3153 0.1984 0.0250 0.0156 
DS-HC-260-4 0.3002 0.1710 0.0225 0.0152 
Note: ND represent not determined. 
Cd content were below the detection limit in all samples. 
  
 
S6 
 
 
Fig.S1 Schematic diagram of HTC process. 
Sludge preparation Solid-liquid separationBatch HTC reaction
Process water
HCs


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Jean-Antoine Chaptal (1756–1832) : premier chimiste disciple de Lavoisier