Bioinorganic Chemistry and Applications

Bioinorganic Chemistry and Applications / 2021 / Article

Research Article | Open Access

Volume 2021 |Article ID 6638229 | https://doi.org/10.1155/2021/6638229

Ahmed Gaber, Walaa F. Alsanie, Robson F. de Farias, Moamen S. Refat, "Preparation and Thermogravimetric and Antimicrobial Investigation of Cd (II) and Sn (II) Adducts of Mercaptopyridine, Amino Triazole Derivatives, and Mercaptothiazoline Organic Ligand Moieties", Bioinorganic Chemistry and Applications, vol. 2021, Article ID 6638229, 10 pages, 2021. https://doi.org/10.1155/2021/6638229

Preparation and Thermogravimetric and Antimicrobial Investigation of Cd (II) and Sn (II) Adducts of Mercaptopyridine, Amino Triazole Derivatives, and Mercaptothiazoline Organic Ligand Moieties

Academic Editor: Guillermo Mendoza-Diaz
Received09 Dec 2020
Revised27 Feb 2021
Accepted02 Apr 2021
Published16 Apr 2021

Abstract

The solid adducts of SnCl2.(3amt).H2O, SnCl2.2(3amt).H2O, CdCl2.(3amt), CdCl2.2(3amt), SnCl2.(2mct).0.5H2O, SnCl2.2(2mct), CdCl2.(2mct), CdCl2.2(2mct).H2O, SnCl2.(2mcp).1.5H2O, >2.2(2mcp).4H2O, CdCl2.(2mcp), CdCl2.2(2mcp), SnCl2.(4amt).4H2O, SnCl2.2(4amt).1.5H2O, CdCl2.(4amt).H2O, and CdCl2.2(4amt) (where the 3amt, 4amt, 2mct, and 2mcp represent 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole, 2-mercaptothiazoline, and 2-mercaptopyridine simple organic chelates, respectively) were prepared using a solid-state route and investigated by CHN elemental analysis and infrared spectroscopy. Additionally, we investigated the thermogravimetric characterization and antimicrobial proprieties. It is verified that for 3amt and 4amt adducts, the coordination occurs through nitrogen atom. For 2mct compounds, the coordination occurs through nitrogen (Sn) or sulfur (Cd). For 2mcp adducts, both coordination sites nitrogen and sulfur are involved. By examination of TG curves, it is confirmed that for each hydrated compounds, the first mass loss step is linked with the release of water molecules followed by the release of ligand molecules and sublimation of the metal chloride. Furthermore, it is verified that, considering only the release of ligand molecules (3amp, 4amp, 2mct, or 2mcp), the cadmium adducts are always more stable than the correspondent tin adducts probably due to the formation of cross-linking bonds in these compounds. Finally, of these 16 adducts, 14 showed antimicrobial activities against different bacterial and fungal strains.

1. Introduction

In the past decades, the problem of multidrug-resistant microorganisms has reached an alarming level worldwide, and the synthesis of new antimicrobial compounds has become an urgent need to treat microbial infections. Organic compounds that include heterocyclic ring systems continue to attract significant interest due to their wide range of biological elements [1]. The nucleus 1,2,4-triazole is incorporated into a variety of important therapeutic agents, which mainly exhibit antimicrobial activities [1, 2]. Among the various five-membered heterocyclic systems, 1,2,4-triazoles and 1,3,4-thiadiazoles and their derivatives gain importance because they constitute the structural features of many bioactive compounds [2]. Triazole and thiadiazole rings are known to be included in the structure of various drugs [3, 4]. From these classes of heterocyclic compounds, the synthesis of novel derivatives of 1,2,4-triazole-3-thionate and 2-amino-1,3,4-thiazole has attracted great interest due to various biological properties such as antibacterial [5, 6], antifungal [7], antituberculosis [8, 9], interferon [10], antioxidant [11], antitumor [12], anti-inflammatory [13, 14], and anticonvulsant [15].

The thermogravimetry analysis technique is employed to identify the acceptability level regarding the coordination nature in between the central metal ions and different kinds of interesting biomolecule chelates, such as amino acids [16], caffeine molecule [17], or chemical materials that have a biological behavior as ethylene- and propylene-urea as well as ethylene-thiourea [18]. Moreover, the thermogravimetric information shows very close relationships with the calorimetric data [19] and the spectral data [20].

The main goal of this article is to investigate the synthesis, thermal analyses, and antimicrobial data of the sixteen solid adducts for the Cd (II) and Sn (II) metal ions coordinated with the 3amt, 4amt, 2mct, or 2mcp organic molecules. The molecular structural formulas of 3amt, 4amt, 2mct, and 2mcp are displayed in Figure 1. The sixteen solid adducts are SnCl2.(3amt).H2O, SnCl2.2(3amt).H2O, CdCl2.(3amt), CdCl2.2(3amt), SnCl2.(2mct).0.5H2O, SnCl2.2(2mct), CdCl2.(2mct), CdCl2.2(2mct).H2O, SnCl2.(2mcp).1.5H2O, SnCl2.2(2mcp).4H2O, CdCl2.(2mcp), CdCl2. 2(2mcp), SnCl2.(4amt).4H2O, SnCl2.2(4amt).1.5H2O, CdCl2.(4amt).H2O, and CdCl2.2(4amt).

2. Materials and Methods

All used reagents were purchased from Sigma-Aldrich and were utilized with no additional purification.

All solid Cd(II) and Sn(II) adducts were prepared by the solid-state pathway by grinding stoichiometric amounts of metal halides and organic moieties (3amt, 4amt, 2mct, and 2mcp) in a mortar for 70 minutes at room temperature (27°C). The prepared solid adducts were dried under vacuum at room temperature for 24 h. This solid-state pathway was successfully used to enhance coordination reactions [2124] as an alternative to conventional synthesis in solution. The synthesis is performed at room temperature, and where no solvent is used, any unwanted reaction to the metal cation is avoided. The infrared spectra result considering both free organic ligands and sixteen solid adducts proved that there are no free ligand particles after the grinding process.

C, H, and N elemental analysis were performed using a Perkin-Elmer 2400 analyzer. Infrared spectra of the solid adducts as a powder in situ KBr discs were scanned using a Gengis II FTIR apparatus within the 4000–400 cm−1 range, with a resolution of 4 cm−1. Thermogravimetric diagrams under N2 atmosphere were analyzed on the Shimadzu TG-50H apparatus with a heating rate of 15°C min−1.

Tin(II) and cadmium(II) contents were determined by gravimetry by the direct ignition of the adducts at 600°C for 3 h till constant weight. The residue was then weighted in the forms of SnO and CdO, respectively. The Mohr method uses chromate ions as an indicator in the titration of chloride ions with a silver nitrate standard solution. After all the chloride precipitated as white silver chloride, the first excess of titrant results in the formation of a silver chromate precipitate, which signals the end point.

Preparation of standard AgNO3 solution: 9.0 g of AgNO3 was weighed out, transferred to a 500 mL volumetric flask, and made up to volume with distilled water. The resulting solution was approximately 0.1 M. This solution was standardized against NaCl. Reagent-grade NaCl was dried overnight and cooled to room temperature. 0.25 g portions of NaCl were weighed into Erlenmeyer flasks and dissolved in about 100 mL of distilled water. In order to adjust the pH of the solutions, small quantities of NaHCO3 were added until effervescence ceased. About 2 mL of K2CrO4 was added, and the solution was titrated to the first permanent appearance of red Ag2CrO4.

The antimicrobial activity of all adducts were performed as previously explained in detail by Gaber et al. [21]. Escherichia coli and Pseudomonas aeruginosa were used as Gram-negative bacteria, whereas Bacillus subtilis and Staphylococcus aureus were used as Gram-positive bacteria. In addition, Aspergillus flavus and Candida albicans were used as fungal strains. Diameters of the inhibition zones around the hole were calculated [21].

3. Results and Discussion

Table 1 shows the data of the elemental analysis. These results are like the proposed formulas. Additionally, the main infrared bands are displayed in Tables 25. Before a discussion on the infrared data, it is important to note that considering (3amt and 4amt) and (2mct and 2mcp), organic molecules have a rich electron donor sites through the lone pair of electrons presented on the nitrogen and sulfur atoms, respectively. Moreover, for the four chelates, there is more than one potential coordination site, which makes them able, at the very first moment, to act as cross-links.


AdductsM.wt% C% H% N
Calc.FoundCalc.FoundCalc.Found

SnCl2.(3amt).H2O291.688.228.112.052.0219.1918.94
SnCl2.2(3amt).H2O375.7612.7712.252.662.6129.8129.44
CdCl2.(3amt)267.378.978.891.491.4520.9420.73
CdCl2.2(3amt)351.4713.6513.622.272.2031.8731.48
SnCl2.(2mct).0.5H2O317.8111.3310.991.891.844.404.35
SnCl2.2(2mct)428.0216.8216.322.332.286.546.43
CdCl2.(2mct)302.5211.9011.741.651.594.624.55
CdCl2.2(2mct).H2O439.7316.3716.222.732.686.376.18
SnCl2.(2mcp).1.5H2O327.7718.3118.192.442.414.274.15
SnCl2.2(2mcp).4H2O483.9424.8024.573.723.685.785.74
CdCl2.(2mcp)294.4820.3720.221.691.684.754.72
CdCl2.2(2mcp)405.6529.5829.292.462.456.906.84
SnCl2.(4amt).4H2O345.686.946.913.473.4116.1915.98
SnCl2.2(4amt).1.5H2O384.7612.4812.342.862.7929.1128.96
CdCl2.(4amt).H2O285.378.408.342.102.0719.6219.48
CdCl2.2(4amt)351.4713.6513.512.272.2631.8731.83


3amtCdCl2-(3amt)CdCl2-2(3amt)SnCl2-(3amt)SnCl2-2(3amt)Assignments

3398 s3419 ms3340 ms3312 w3349 vw(N-H); NH2
3326 mw3356 w3310 vw
3316 mw3258 vw

3182 mw3213 w3212 ms3155 mw3155 ms(N-H); NH2
3131 w3153 vw

1647 vs1652 vs1645 w, sh1688 vs1677 vsδb(NH2)
1590 s1573 w1594 vs1569 ms1566 msν(C=N)
1533 s1537 s1560 vsν(N=N)
1480 w1479 vs

1418 s1429 ms1374 vs1405 mw1415 wRing breathing bands
1389 ms1373 w1339 ms1326 s
1332 ms

1275 vs1283 s1248 vs1257 ms1263 wρr (NH2)
1217 vs1250 vw1213 ms1125 vw1125 msν(C-N)
1219 vs1144 vs
1144 w

1045 vs1088 w1083 vs1048 s1066 sρw (NH2)
945 vs1057 s1011 vs951 vs950 vs
991 s

873 vs901 s884 s860 ms867 sρt (NH2)
830 s740 ms747 sh748 w, sh773 ms
729 vs693 vw726 ms
644 vs694 vs
642 ms

s = strong; w = weak; m = medium; sh = shoulder; v = very; br = broad; ν = stretching; δ = bending.

4amtCdCl2-(4amt)CdCl2-2(4amt)SnCl2-(4amt)SnCl2-2(4amt)Assignments

3312 w3467 ms3303 s3417 w3418 w, br(N-H); NH2
3368 ms3258 vw3317 ms3277 w, br
3307 ms

3197 w3199 s3198 s3127 ms3129 w, br(N-H); NH2
3139 w3136 s3105 s

1647 vs1618 vs1618 vs1623 vs1685 wδb(NH2)
1533 s1543 s1537 s1539 ms1631 vs
1529 s

1475 ms1474 mw1470 w1465 vw1465 vwRing breathing bands
1404 s1398 s1394 w1402 vw1412 vw
1341 s1346 w1366 vw1363 vw
1318 vw1323 vw

1188 s1209 s1209 ms1207 ms1205 sρr (NH2)
1074 s1145 vw1078 s1164 vw1075sν(CN)
1082 vs1135 vw
1075 s

1016 vw1025 s1015 s1034 s1033 sρw (NH2)
959 ms980 vs984 ms934 ms935 ms

873 s908 w894 ms871 ms875 msρt (NH2)
672 w874 s845 vw690 w, sh661 ms
689 ms686 ms

s = strong; w = weak; m = medium; sh = shoulder; v = very; br = broad; ν = stretching; δ = bending.

2mctCdCl2-(2mct)CdCl2-2(2mct)SnCl2-(2mct)SnCl2-2(2mct)Assignments

2852 w3258 s3258 s3443 s, br3447 ms, br(C-H); –CH2
2948 vw3136 ms3206 ms3207 w(O-H); H2O
2998 w3144 vw3136 w
2947 w2997 w2997 w
2844 w2929 w2848 vw
2845 w

2709 mwν(SH)
2565 mw

1518 vs1515 vs1515 vs1539 vs1539 w, shν(C=N)
1514 sRing breathing bands

1260 w1308 s1305 s1307 s1294 s(C-N)
1217 w1250 vw1249 w1253 w1250 vw(C-N) + ν(C-C)
1160 w1192 ms1193 s1208 w1205 vwν(C-S); C – SH
1102 s1142 w1045 vs1167 w1041 s
1045 vs1038 s

s = strong; w = weak; m = medium; sh = shoulder; v = very; br = broad; ν = stretching; δ = bending.

2mcpCdCl2-(2mcp)CdCl2-2(2mcp)SnCl2-(2mcp)SnCl2-2(2mcp)Assignments

3458 ms, br3448 ms, br3421 ms, br3423 ms, brν(OH); H2O
3196 ms3172 ms3216 ms3073 vw
3126 ms3135 w
3087 s

2709 mwν(SH)
2537 mw

1576 vs1602 vs1585 vs1582 vs1578 vsRing breathing bands
1504 s1517 s1513 s1550 sh1551 sh
1446 ms1443 s1443 s1517 s1438 vs
1418 s1378 s1370 s1438 vs1366 w
1360 s

1275 ms1262 s1252 s1259 vs1262 sν(C=N); aromatic
1246 ms1160 ms1163 s1155 w, sh1179 vwδ(C-H); in-plane bend
1188 vs

1145 vs1134 vs1132 vs1131 s1136 sν(C-S); C – SH
1102 vw1111 vw1109 vw1080 ms1081 ms

s = strong; w = weak; m = medium; sh = shoulder; v = very; br = broad; ν = stretching; δ = bending.

In case of 3amt adducts, the overall decrease observed for the symmetrical and asymmetrical N-H bands suggests that the NH2 group is engaged with the coordination. Furthermore, positive shifts observed for the δb bands reinforce this statement. It is worth noting that the observed shifts are more intense to Sn(II) adducts than to Cd(II), which is probably due to the higher acidity of Sn(II) (larger nuclear effective charge: 5.65 for Sn and 4.35 for Cd). It is verified that the symmetrical N-H bands are more sensitive to this acidity difference since a positive shift is observed for Cd(II) adducts, whereas a negative shift of this band is verified to Sn(II) adducts.

In case of 4amp approximation, the same general orientation is observed for asymmetric and symmetric N-H bands. This fact indicates that in this case, NH2 is involved to a slight degree in the metallic coordination. This hypothesis is reinforced by the fact that for 4amp, the ringed breathing bands exhibit a negative shift (compared to free chelates and synthesized solid adducts), whereas positive shifts are observed in 3amp. Therefore, for 4amp adducts, the two “isolated” nitrogen atoms are the main coordination sites. Suggested coordination modes for 3amp and 4amp molecules are shown schematically in Figure 2.

As explicatory examples, the infrared spectra of 3amt solid adducts are shown in Figure 3.

In case of 2mct adducts, positive shifts of the νC = N band are observed for Sn(II) adducts, whereas negative shifts are verified to Cd(II) adducts. Such fact suggests a coordination through nitrogen to Sn(II) and a coordination through sulfur to Cd(II) in agreement with the fact that the nitrogen atom is a hard base and that Sn(II) is a harder acid than Cd(II).

For 2mcp adducts, the negative shifts observed for the ν(C-S); C-SH and ν(C=N) aromatic bands suggest that, in this case, both coordination sites N and S are involved in the coordination process for both cations considered.

The data of thermogravimetric curves for the 16 solid adducts are demonstrated in Figure 4. The main TG data are elucidated in Table 6.


AdductStepti (°C)Degradation tf (°C)Process onset (°C)Mass loss (%)

SnCl2.(3amt).H2O15538223826.7
238556047335.5
SnCl2.2(3amt).H2O145102765.1
216044532040.0
344760651727.2
CdCl2.(3amt)128033130753.7
233240634812.8
347866056929.3
CdCl2.2(3amt)118827123424.1
234844840116.8
344968158743.0
SnCl2.(2mct).0.5H2O131.483503.3
212734423743.2
33464614047.5
44626155136.2
SnCl2.2(2mct)112026020444.0
226134128810.2
33424303784.7
44315955138.9
55966566071.1
CdCl2.(2mct)118127622330.2
249765058341.3
CdCl2.2(2mct).H2O113627620743.2
227748538415.4
34866285519.3
SnCl2.(2mcp).1.5H2O11101991548.0
220035528555.4
34216545343.1
SnCl2.2(2mcp).4H2O110322115414.3
222234930282.1
35846705851.8
CdCl2.(2mcp)118630924423.3
231045939112.6
346064757647.0
46487516758.6
CdCl2.2(2mcp)113927421535.8
22763493015.2
335148239910.1
448364957226.9
SnCl2.(4amt).4H2O1461451102.8
221029926915.7
330042535537.0
442861651510.2
SnCl2.2(4amt).1.5H2O1631911336.8
219231925739.2
332040735818.2
449761954514.2
CdCl2.(4amt).H2O1881761236.7
227438132821.1
33824594077.9
446065558351.3
CdCl2.2(4amt)119528925617.9
229039032423.7
33924564204.8
445767958347.5

ti and tf are the initial and final temperatures of the thermal degradation process, respectively.

For each TG curve, the experimental mass losses (±5%) are similar to the proposed formulas. It is possible to verify that for all hydrated compounds, the first mass loss step is associated with the release of water molecules followed by the release of ligand molecules and sublimation of the metal chloride. Furthermore, it is verified that, considering only the release of ligand molecules (3amp, 4amp, 2mct, or 2mcp), the cadmium adducts are always more stable than the correspondent tin adducts. Since the infrared data suggest that the metal-to-ligand interaction is higher for tin adducts, this last result is an expected one, unless we take into account that the cadmium adducts generally polymerize [2227] and so there is, probably for these compounds, the formation of cross-linking bonds, leading to more stable compounds, from a thermal point of view.

The antimicrobial effect of the adducts was measured against a variety of microorganisms including bacteria and fungus (Table 7 and Figure 5). The no-growth zones around the hole indicated the inhibiting activity of the adducts on the microbe. These were calculated and compared with the ampicillin as an antibacterial agent or amphotericin B as an antifungal agent. The adduct CdCl2.2(2mct).H2O and CdCl2.(2mct) showed the highest antimicrobial activities followed by SnCl2.(2mcp).1.5H2O among all other adducts. On other hand, the CdCl2.(3amt) and CdCl2.(4amt).H2O have no effect on any bacteria or fungal strains (Table 7). The antimicrobial activities of these adducts might be caused by a direct interaction of Cd (II) or Sn (II) ions with proteins, enzymes, nucleic acids, and membranes of microbe cells.


The adductsGram-negative bacteriaGram-positive bacteriaFungi
E. coliP. aeruginosaB. subtilisS. aureusA. flavusC. albicans

Control: DMSO0.00.00.00.00.00.0
Ampicillin (Antibacterial agent)221720180.00.0
Amphotericin B (Antifungal agent)0.00.00.00.01719
SnCl2.(3amt).H2O101012110.023
SnCl2.2(3amt).H2O151313150.014
CdCl2.(3amt)0.00.00.00.00.00.0
CdCl2.2(3amt)121212150.011
SnCl2.(2mct).0.5H2O90.010100.00.0
SnCl2.2(2mct)999210.00.0
CdCl2.(2mct)161514201417
CdCl2.2(2mct).H2O262826323135
SnCl2.(2mcp).1.5H2O161516210.09
SnCl2.2(2mcp).4H2O131414140.00.0
CdCl2.(2mcp)111011100.016
CdCl2.2(2mcp)141312160.013
SnCl2.(4amt).4H2O90.00.00.00.00.0
SnCl2.2(4amt).1.5H2O10912130.09
CdCl2.(4amt).H2O0.00.00.00.00.00.0
CdCl2.2(4amt)90.00.090.00.0

4. Conclusion

The adducts SnCl2.(3amt).H2O, SnCl2.2(3amt).H2O, CdCl2.(3amt), CdCl2.2(3amt), SnCl2.(2mct).0.5H2O, SnCl2.2(2mct), CdCl2.(2mct), CdCl2.2(2mct).H2O, SnCl2.(2mcp).1.5H2O, SnCl2.2(2mcp).4H2O, CdCl2.(2mcp), CdCl2.2(2mcp), SnCl2.(4amt).4H2O, SnCl2.2(4amt).1.5H2O, CdCl2.(4amt).H2O, and CdCl2.2(4amt)—where 3amt = 3-amino-1,2,4-triazole; 4amt = 4-amino-1,2,4-triazole; 2mct = 2-mercaptothiazoline; and 2mcp = 2-mercaptopyridine—were synthesized by a solid-state route and characterized by CHN elemental analysis and infrared spectroscopy. A thermogravimetric study was also performed. It is verified that, for all compounds, the monoadducts are the most stable ones. Such fact agrees with a higher ionic and covalent character of the metal-ligand bond for such compounds. From the result, it can be concluded that 14 of the 16 compounds have a good biological activity against these microorganisms.

Data Availability

The data used to support the findings of this study are included within the article.

Conflicts of Interest

The authors declare no conflicts of interest.

Acknowledgments

The authors are grateful to Taif University for supplying essential facilities and acknowledge the support of Taif University Researchers Supporting Project (TURSP-2020/39), Taif University, Taif, Saudi Arabia.

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