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Synthesis and characterization of a new complex based on antibiotic: Zirconium complex

  • Sabrina Benmebarek EMAIL logo , Sabiha Anas Boussaa , Imad Eddine Benmebarek , M’hamed Boudraa and Hocine Merazig
Published/Copyright: March 24, 2023
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Applied Rheology
From the journal Applied Rheology Volume 33 Issue 1

Abstract

It is well known that sulfonamide derivatives, through exchange of different functional groups without modification of the –S(O)2N(H)– function, can exhibit a wide variety of pharmacological activities. In addition, some metal complexes of these ligands have been prepared to promote rapid healing of burns in humans and animals, for example, the complex of Zn(ii) sulfadiazine. Their effectiveness does not depend solely on the slow release of the metal ion, but rather strongly on the nature of the material to which the metal is bound. Given the ability of sulfonamide derivatives to coordinate with metal atoms in different ways, considerable interest in the synthesis and structural aspects of new complexes has arisen. These results confirm that the significant chemical capacity of sulfonamides to act as ligands is based on the acidity of its –S(O)2N(H)– function, which gives a donor anionic ligand, allied to the presence of atoms vicinal to nitrogen, sulfur or oxygen of the heterocyclic ring, which provide the stereochemical requirements for the realization of complexes with monodentate ligand, chelating agent or bridging ligand, providing monomeric structures, dimeric arrangements and polymers. In addition, the aromatic amino group is responsible for the chemical versatility of the sulfonamides, since it can act as a coordination site, as well as a reactive site for chemical modifications of sulfonamide complexes with very interesting biological purposes. In the present work, the synthesis and structure of a novel sulfanilamide complex: nitro (4-aminobenzenesulfonamide) zirconium was presented. Characterization of the complex was performed by infrared spectroscopic, thermogravimetric and X-ray diffraction analysis.

Keywords: single-crystal; X-ray study; hydrothermal synthesis; zirconium sulfanilamide

1 Introduction

Sulfanilamide has been successfully used as effective chemotherapeutic agents for the prevention and cure of bacterial infections in human biological systems [1]. In addition, sulfanilamide-based drugs (Figure 1) and their complexes have applications as diuretic drugs [2], anti-glaucoma [3] or anti-epileptics [4], antifungals [5], antivirals [6], anti-tumor [7,8] and anti-inflammatory drugs [9], among others [10,11,12,13]

Figure 1 ORTEP diagram of Sulfanilamide.
Figure 1

ORTEP diagram of Sulfanilamide.

Sulfanilamide exists in three crystallographic forms α, β and γ [14,15,16]. The structural study of this compound shows how the polymorphism of sulfanilamide is related to its polyvalent hydrogen bonding capabilities [17]. The polymorphism of sulfanilamide has been widely studied, but sporadically over a number of years [18].

The detailed study of the crystalline structure of the three forms of sulfanilamide [19,20,21,22,23] and the characterization of sulfanilamide and its complex derivatives have been reported [24,25,26,27]. Meanwhile, sulfonamides have attracted increasing attention to supramolecular chemistry and supramolecular medicinal chemistry [28], as it combines the functionalities required for various biological activities and the coordination of the metal through phenylamino groups and sulfonylamino groups. Recently, modification of existing drugs through better coordination at a metal center has attracted considerable interest [29,30,31,32,33].

In this study, the coordination of sulfanilamide ligand with transition metals was studied and the synthesis and structure of a novel sulfanilamide complex, nitro (4-aminobenzenesulfonamide) zirconium, is presented.

Characterization of the complex was performed by infrared spectroscopic, thermogravimetric (TG) and elemental analysis methods.

In addition, the technique of X-ray diffraction was used and the structural studies of the complex are represented.

2 Materials and methods

The complex was obtained by dissolving PbZrO3 in a solvent and then adding sulfanilamide H2NC6H4O4NH2 with stirring in a hydrothermal bomb. The principle of this method is to introduce the dissolved reagents into a Teflon-coated stainless steel autoclave which is heated to increase the pressure in a chamber set at a constant temperature of 120°C for 72 h.

Then, the bomb is cooled after taking out from the enclosure.

After that, the powder was washed several times and filtered and let to evaporate in the open air.

After several days, orange crystals appeared as needles, which are insoluble in water, Figure 2.

Figure 2 Complex (1).
Figure 2

Complex (1).

The Fourier transform infrared (FTIR) spectrometer, Thermo Nicolet Nexus 670, was used for the determination of the sulfamide bonds.

Complex (1) was studied by single crystal X-ray diffraction. The crystallographic measurements were carried out at 293 K on an APEX2 CCD automatic diffractometer [34] using molybdenum Kα radiation (λ = 0.71073 Å) and a graphical monochromator equipped with a cryogenic system allowing low temperature recording. The refinement and the reduction of the data of the structure were realized by the software SAINT [34].

The structure has been resolved using the SIR-2002 program [35] and then refined using the least squares method with the program: SHELXL-2013 [36], these programs are found in the complete WINGX software [37]. Graphical representations were made using software: ORTEP-3 [38], Mercury [39] and DIAMOND [40].

The thermal study of the compound, [Zr(C12H17N4O4S2)2]2+·2(NO3)−, was performed byTG on a “Setaram Setsys 16/18” thermo balance under vacuum under oxidizing atmosphere (O2), 40 ml/min. In a typical experiment, 3–5 mg of the sample was heated from 0 to 1,000°C at a heating rate of 10°C/min, this amount of sample gave a full-scale deviation with instrument used.

3 Results

3.1 FTIR analysis

In order to specify the binding mode and the effect of metal ions on the sulfanilamide ligand [41,42,43,44,45,46], the free ligand IR spectra and the synthesized Zr (1) and Zn (2) [47] metal complexes were studied and assigned on the basis of a careful comparison of their spectra (Figures 3–5).

Figure 3 IR spectrum of the sulfanilamide in the range of 4,000–400 cm−1.
Figure 3

IR spectrum of the sulfanilamide in the range of 4,000–400 cm−1.

Figure 4 IR spectrum of the complex (2) in the range of 4,000–400 cm−1.
Figure 4

IR spectrum of the complex (2) in the range of 4,000–400 cm−1.

Figure 5 IR spectrum of the complex (1) in the range of 4,000–400 cm−1.
Figure 5

IR spectrum of the complex (1) in the range of 4,000–400 cm−1.

The number of calculated vibration waves, positions and assignments for sulfanilamide is compared with the two synthesized products shown in Table 1.

Table 1

Number of calculated vibration waves, positions and assignments for the sulfanilamide and complex (1) and (2) measured by infrared

ν measured ν IR (cm−1) Sulfanilamide ν IR (cm−1) Complex (2) ν IR (cm−1) Complex (1) Assignments
3,490 3,478s 3,550 3,550 ν aNH2 (an)
3,464 ν aNH2 (sulfo)
3,384 3,375s ν sNH2 (an)
3,345 3,266s 3,250 3,250 ν sNH2 (sulfo)
1,634 1,629s 1,600 1,650 δNH2 (an)
1,577 1,573w 1,550 1,550 δNH2 (sulfo)
1,346 1,313vs br 1,335 1,300 ν aSO2
1,143 1,147vs 1,150 1,150 ν sSO2
907 900s 900 900 νS–N
687 683 s 600 ± 50 600 ± 50 ωNH2 (sulfo)
652 626 m 630 650 δSO2
573 563 s 580 / ωSO2
571 540 s 550 ± 50 550 ± 50 ωNH2 (an)

ν: stretching, δ: in-plane deformation, ω: wagging, br: broad, v: very, m: medium, s: strong, w: weak, sulfo: sulfonamide, an: aniline. Subscripts – a: asymmetric, s: symmetric.

3.2 DRX analysis

The complex [Zr(C12H17N4O4S2)2]2+·2(NO3)− (1) crystallizes in a space group (Pbca) of the orthorhombic system. This complex differs from the complex (2) by the coordination of the sulfanilamide ligand. The asymmetric unit comprises a metal ion Zr(ii), two metal-coordinated sulfanilamide ligands and a crystallographically independent nitro anion, all located at general positions (Figure 6).

Figure 6 Asymmetric unit of the complex (1): [Zr(C12H17N4O4S2) 2]2+·2(NO3)−.
Figure 6

Asymmetric unit of the complex (1): [Zr(C12H17N4O4S2) 2]2+·2(NO3)−.

3.3 TG analysis

The TG analysis provides a precise indication of the overall mass loss, but provides no indication of the nature of the gases emitted.

The TG analysis of the compound [Zr (C12H17N4O4S2)2]2+·2(NO3)− is presented in Figure 7.

Figure 7 TG analysis of the compound [Zr (C12H17N4O4S2)2]2+·2(NO3)− at a heating rate of 10°C/min.
Figure 7

TG analysis of the compound [Zr (C12H17N4O4S2)2]2+·2(NO3)− at a heating rate of 10°C/min.

4 Discussion

4.1 FTIR links

Recently, some structural and vibrational research works have been reported for sulfanilamide and its metal complexes.

In their study, the number of calculated vibration waves, positions and assignments for the two synthesized products are presented in Table 1 and compared with the literature data.

The results found are in good agreement with the literature data.

4.2 Description of the crystal structure of complex (1)

The coordination polyhedron of the metal ion Zr(ii), of the type [ML4] (L = Nsulfanilamide, Osulfanilamide), has a distorted pyramidal geometry.

This polyhedron is generated from an equatorial plane (ZrN3), comprising three nitrogen atoms (N1, N3, N4) belonging to the three chelate sulfanilamide ligands; the axial position involves the oxygen atom (O1) from a fourth sulfanilamide ligand (Figure 8). The Zr atom and the three nitrogen atoms that define its coordination environment are almost in the same plane. The sulfanilamide ligand in this molecule is “bidentate.”

Figure 8 Environment of zirconium in the compound (1) [Zr(C12H17N4O4S2)2]2+·2(NO3)−.
Figure 8

Environment of zirconium in the compound (1) [Zr(C12H17N4O4S2)2]2+·2(NO3)−.

The deformation of this polyhedron is mainly due to the values of the angles N1–Zr–N3 (141(10)°), N3–Zr–N4 (83(10)°) and N1–Zr–N4 (136(7)°) imposed by the coordination of the ligand sulfanilamide. The Zr–N4 bond (2.7(8)Å) is longer than similar bonds in the same plane, Zr–N1 and Zr–N3 (2.3(8)Å–2.3(10)Å) respectively. The distances Zr–N4 (2.7(8)Å) and Zr–O1 (2.5(7)Å) are much larger than those observed in sulfanilamide complexes [48,49]. Table 2 summarizes the main lengths and bond angles of the coordination sphere of complex (1).

Table 2

Lengths and main binding angles in complex (1)

Complex 1 Distance (Å) Angles (°)
Zr–N1 2.3(8) N1–Zr–N3 141(10)
Zr–N3 2.3(10) N1–Zr–O1 93(10)
Zr–O1 2.5(7) N3–Zr–O1 89(10)
Zr–N4 2.7(8) N1–Zr–N4 136(7)
N3–Zr–N4 83(10)
O1–Zr–N4 85(10)

The sulfanilamide ligand adopts a “bidentate” coordination mode in repetitive and symmetrical chain. The latter coordinates in two ways: the first ligand coordinates the metal with oxygen O1 of the sulfonylamino function and nitrogen N1 of the phenylamino function, while the second ligand coordinates the metal with the N3 nitrogen of the phenylamino function and the N4 nitrogen of the sulfonylamino function. This coordination mode generates the polymer structure shown in Figure 9.

Figure 9 Coordination mode of the complex (2): [Zr(C12H17N4O4S2)2]2+·2(NO3)−.
Figure 9

Coordination mode of the complex (2): [Zr(C12H17N4O4S2)2]2+·2(NO3)−.

As for the nitrate anion that accompanies the zirconium complex is not coordinated, each NO 3 − anion entity accompanies a metal.

The sequence of zirconium polyhedra with sulfanilamide ligands is shown in Figure 10 on the (a–c) plane. The arrangement of these tetrahedra appears in the form of metal layers separated by the organic layers of the sulfanilamide. Note that each pair of polyhedra is inverted relative to each other, accompanied by NO 3 − nitro anion pair.

Figure 10 Chaining polyhedra formed by the environment of molybdenum in the plane (a–c).
Figure 10

Chaining polyhedra formed by the environment of molybdenum in the plane (a–c).

4.3 Hydrogen bonds

The structure of the sulfanilamide ligand confers on the complex (1), a polynuclear structure. Thus, within this structure, the cohesion between the molecules is essentially ensured by two types of intra and intermolecular hydrogen interactions Figure 11, Table 3.

Figure 11 Representation of inter and intramolecular interactions of hydrogen type in the asymmetric unit of complex (1). The blue dots represent the intramolecular interactions N–H…O, C–H…O, The red dots represent the intermolecular N–H…O interactions.
Figure 11

Representation of inter and intramolecular interactions of hydrogen type in the asymmetric unit of complex (1). The blue dots represent the intramolecular interactions N–H…O, C–H…O, The red dots represent the intermolecular N–H…O interactions.

Table 3

Intra and intermolecular hydrogen bonds in complex (1)

Complex (1) D–H…A D–H (Å) H…A (Å) D…A (Å) D–H…A (°) Type
N1–H(1 A)…O3 0.90 2.29 3.162(5) 164 Moderate
N1–H(1B)…O6 0.90 2.36 3.222(6) 162 Moderate
N2–H(2B)…O5 intra 0.89 2.39 3.095(7) 136 Moderate
N2–H(2B)…O4 0.89 2.43 2.879(6) 112 Weak
N2–H(2 C)…O6 0.89 2.13 2.914(6) 147 Moderate
N3–H(3 A)…O2 0.90 2.59 3.139(6) 116 Weak
N3–H(3 A)…O3 0.90 2.50 3.028(6) 128 Weak
N3–H(3B)…O6 intra 0.90 2.14 3.028(4) 169 Moderate
N4–H(4 A)…O2 0.90 2.25 2.926(6) 131 Moderate
N4–H(4B)…O6 0.90 2.57 3.322(6) 141 Moderate
N4–H(4B)…O7 0.90 2.15 3.034(7) 166 Moderate
C4–H4…O1 intra 0.93 2.49 2.873(7) 105 Weak
C8–H8…O4 intra 0.93 2.56 2.919(7) 103 Weak

Codes of symmetry: (1) 1/2 − x, − 1/2 + y, z; (2) x, 1/2 − y, − 1/2 + z; (3) x, y, z; (4) 1/2 + x, 1/2 − y, − z; (5) 1/2 − x, − 1/2 + y, z; (6) −x, 1/2 + y, 1/2 − z; (7) −x, 1 − y, − z; (8) x, y, z; (9) −x, − y, − z; (10) x, 1/2 − y, − 1/2 + z; (11) x, 1/2 − y, 1/2 + z; (12) x, y, z; (13) x, y, z.

4.4 Intramolecular hydrogen interactions, in the case of chelate ligands

Four intramolecular hydrogen bonds connect the nitrogen atoms (donors: D) of the sulfanilamide and the oxygen atom (acceptors: A) of the nitro anion NO 3 − ; they also connect the carbon atoms (donors: D) of the sulfanilamide and the oxygen atom (acceptors: A) of the sulfanilamide function of the ligand, (Figure 11). The data for these intramolecular interactions are summarized in Table 3.

According to Steiner [50], hydrogen bonds can be classified into three different categories based on distances: D–A, H. A and angles D–H. A (Table 3).

The structure of the complex (1) also reveals the existence of intermolecular interactions of the hydrogen type. These bridges involve contacts N–H. O (Table 3, Figure 11) which generates a three-dimensional network of hydrogen bonds of moderate strength [42] (distance D. A between 2.5 and 3.2 Å and angles D–H. A superior at 130°) and other low (distance D. A > 3.2 Å and angles D–H. A greater than 90°) ensuring the junction between the different ligands of the cation and the anion between the molecules of the crystal lattice. The very close weak bonds are explained by the association between two large molecules. The refinement was done by geometric calculation. The lengths and angles of the hydrogen bonds, listed in Table 2, are of the same order of magnitude as those observed in complexes containing sulfanilamide [51,52,53,54,55].

4.5 TG properties of complex (1)

The TG curve of the ligand alone of “sulfanilamide” already studied in the literature [56] can be used as a qualitative tool in the identification of a new compound based on unknown sulfonamide by comparing its shape to the shape of the curve obtained, Figure 12.

Figure 12 TG analysis of the sulfanilamide ligand [56], (NH2C6H4SO2NH2), at a heating rate of 10°C/min.
Figure 12

TG analysis of the sulfanilamide ligand [56], (NH2C6H4SO2NH2), at a heating rate of 10°C/min.

Research on sulfanilamide and these derivatives was conducted to see if the curves could be obtained and if they were unique, so that the sulfonamide analysis could become a more practical analysis. Further development of the technique could lead to the determination of the components of a mixture and subsequently to a quantitative analysis of the drugs. Several articles concerning the thermal decomposition of sulfones [57,58] occurring according to reaction (I) have been published in the literature.

(I) R -SO 2 -R' ⟶ Δ R - SO 2 R o ⟶ Δ R o + SO 2

The zirconium complex has a thermal decomposition curve (Figure 7) different from that of the Zn (2) complex, similar to a number of sulfanilamide reported in the literature [59]. It is stable up to 220°C or it begins to decompose continuously up to 660°C to give zirconium oxide with a total mass loss of 65%.

5 Conclusion

In the present work, the structural and spectroscopic characterizations and the TG analysis of a new Zr(ii) complex were presented, these finding confirm that the formed complex could be applied as an efficient antibiotic. The complex (1) is a charged discrete structure that consists of a molybdenum metal ion coordinated to four sulfanilamide ligands and two NO 3 − nitrate anions. Sulfanilamide is “bidentate” in this coordination mode, where the first ligand coordinates the metal with an oxygen O of the sulfonylamino function and a nitrogen N of the phenylamino function, while the second ligand coordinates the metal with the nitrogen N of the phenylamino function and the N nitrogen of the sulfonylamino function. The structure is polynuclear.

The sulfanilamide compounds used for the prevention and treatment of bacterial infections in human biological systems have been investigated. Because the applications of “sulfadrugs” based on sulfanilamide metal have interesting antimicrobial activities. Our research on sulfanilamide-based inorganic compounds has allowed us to synthesize and characterize, by single-crystal X-ray diffraction, new compounds rich in inter and intramolecular interactions via hydrogen bonds between neutral or cationic and anionic entities.

Acknowledgments

This work was supported by the Research Unit in Environmental Chemistry and Molecular Structure, CHEMS, University of Constantine 1, in Algeria and finalized in collaboration with the Materials Science team of the University of Valencia (ICMUV), Spain. My thanks go to the MESRS and the ATRST (Ministry of Higher Education and Scientific Research and the Agency for Thematic Research in Science and Technology – Algeria) via the PNR program of financial aid and in particular the scientific park in Spain.

  1. Funding information: Authors state no funding involved.

  2. Author contributions: Sabrina Benmebarek has made the elaboration, the conception and the design and the acquisition of the work. Sabiha Anas Boussaa substantively revised the paper. Imad Eddine Benmebarek, M hamed Boudraa, and Hocine Merazig analysed, interpreted the found results.

  3. Conflict of interest: Authors declare that they have no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use

  5. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Received: 2023-01-17
Revised: 2023-02-14
Accepted: 2023-02-15
Published Online: 2023-03-24

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/arh-2022-0142
Keywords for this article
single-crystal; X-ray study; hydrothermal synthesis; zirconium sulfanilamide
Creative Commons
BY 4.0

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