INTRODUCTION:

Hydrazones are a class of organic compounds with a wide range of applications that have made them an effective research center. They belong to a class of chemical compounds with the fundamental formula R₁R₂C=NNH₂. They are connected to aldehydes and ketones because hydrazine acts on carbonyl compounds (ketones or aldehydes) to replace the oxygen atom. Typically, hydrazones are named after the carbonyl compounds that they are derived from. In heterocyclic chemistry, hydrazone moieties are significant. One key class of molecules for the development of novel drugs is the azomethine -NHN=CH- proton.^1,2 They serve as intermediates in the Wolff-Kishner reaction and reactants in a number of significant processes, including the Bamford-Stevens reaction, the Shapiro reaction, and the Barton hydrazone iodination to create vinyl compounds.^3,4 Hydrazones also function as building blocks in the synthesis of heterocyclic molecules. Chemists can obtain a wide range of heterocycles, such as pyrazoles, pyridazines, and pyrimidines, by using hydrazones as precursors. These heterocyclic compounds are widely used in materials research, agrochemicals, and medicines because they frequently show strong biological activity.^5,6 Moreover, hydrazones frequently show signs of crystallinity. Many fields, such as materials science and medication creation, can benefit from this feature. Hydrazones' capacity to crystallize into well-defined forms makes it easier to characterize and purify them, which is essential for medication development and optimization.^7,8 Despite these advantageous characteristics, hydrazones have long been the subject of research, but much of their fundamental chemistry is still unknown. The field of coordination chemistry has been extensively studied in hydrazones, with a great deal of research carried out on their transition metal complexes. Complexes of Hydrazones have gained more attention as the field of bio inorganic chemistry has developed, as it has been realized that many of these complexes could function as models for biologically significant species.^9,10 Hydrazones’ coordination compounds have been documented for their anti-tuberculosis, antibacterial, and corrosion-inhibiting properties.^11,12 Numerous studies have been conducted on the antifungal and antimicrobial characteristics of hydrazones and their transition metal complexes. Nevertheless, more is needed to be known about their thermodynamics parameters, thermal breakdown stabilities and biological characteristics. Therefore, the goal of this work was to create novel methylphenol hydrazone ligands and identify transition metal complexes they form with V(IV), Co(II), and Cu(II) ions that may have antiviral properties.

EXPERIMENTAL:

Materials and methods:

Every chemical that is used is of AR grade. The solvents were purified using normal methods before to use. Materials which include hydrazinephenylmethanol (CAS number: 73454-78-1), 1-phenylethylhydrazine, also known as mebanazine (with CAS number: 29248-55-3), and 2-hydroxy-6-methylbenzaldehyde (with CAS number: 18362-36-2) were all purchased through the Sigmaa Aldrich Chemical Corporation.

Instrumentation:

A Bruker Vance 500 MHz spectrometer was used to scan the ¹H-NMR spectra of the investigated compounds, while a 125 MHz spectrophotometer was used to scan the ¹³C-NMR spectra in a DMSO-d6 solvent. The internal standard, TMS, served as a guide in figuring out the 0.0 ppm. The infrared spectra of the compounds were measured using an FTIR spectrophotometer model FTIR Affinity 1, as KBr disks at room temperature and a range of 4000–400 cm⁻¹. Mettler Toledo was used for TGA research, and its temperature range was 0 to 700 °C, with a heat rate of 10 °C/min. The Waters Alliance 2695 HPLC-Micromass Quattro micro-API Mass Spectrometer was used to evaluate the compounds' electrospray ionization (ESI). Using a method made by Auto Magnetic Susceptibility (Sherwood Scientific), the magnetic susceptibility of the complexes was measured at room temperature using the Gouy Method Model. Pascal's constants for the atoms that make up the complexes were used to compute the correction factor for the prepared complexes. Using dimethylformamide (DMF) as a solvent at 1 × 10⁻³ M, the molar conductance of the complexes was measured at a temperature of 25 °C using a conductivity device made by a Swiss company.

Preparation of HMP and PHP Ligands:

The ligands used in the present investigation have been prepared by condensing hydrazinephenylmethanol and 1-phenylethylhydrazine (mebanazine) with 2-hydroxy-6-methylbenzaldehyde in the following manner. The ethanolic solution of 2-hydroxy-6-methylbenzaldehyde (0.01 mole in 20 mL) was mixed with ethanolic solutions of hydrazinephenylmethanol and 1-phenylethylhydrazine (mebanazine) (0.01 mol in 20 mL).¹³ Two to three drops of piperidine were then added to the mixture as a condensing agent. The resulting solution was refluxed in a water bath for three hours. After it was concentrated, each case's colored precipitates were sorted out overnight. From ethanol, these precipitates underwent filtering, washing, and recrystallization.41 After that, the samples were vacuum-dried over fused calcium chloride before being examined (schemes 1 and 2), producing 95% and 97% yields, m.p. (171–174 °C and 162–165 °C, respectively).

Scheme 1:

Scheme 2:

Synthesis of the complexes:

Vanadyl complexes:

Diaqua 2-[(E)-{2-[hydroxy(phenyl)methyl]hydrazinylidene}methyl]phenol Vanadium(IV) chloride] (HMPV) and Diaqua 2-{(E)-[2-(1-phenylethyl)hydrazinylidene]methyl}phenol Vanadium (IV) chloride (PHPV). To create the vanadyl complexes, 50 mL of dioxane were reacted with 1 mmol, 0.18 g) of VOSO₄.5H₂O and 1 mmol, 0.481 g) of the ligands (HMP and PHP). The result was the vanadyl complexes HMPV and PHPV filtrates, which were then refluxed for two hours. After that, the filtrates were thrice cleaned with dioxane and diethyl ether, yielding dry dark powders (90% and 92% respectively).

Cobalt complexes:

Tetra-aqua 2-[(E)-{2-[hydroxy(phenyl)methyl]hydrazinylidene}methyl]phenol Cobalt (II) chloride, (HMPCo) and 2-{(E)-[2-(1-phenylethyl)hydrazinylidene]methyl}phenol Cobalt (II) chloride, (PHPCo) complexes were prepared by reacting (1 mmol, 0.237 g)cobalt chloride, CoCl₂・6H₂O, and (1 mmol, 0.481 g) ligands (HMP and PHP) with 50 mL Dioxane and refluxing for 2 h to yield brown powders of cobalt complexes with the yields of 98% and 96% respectively.

Copper complex:

Diaqua 2-[(E)-{2-[hydroxy(phenyl)methyl]hydrazinylidene}methyl]phenol Copper(II) chloride, (HMPCu) and 2-{(E)-[2-(1-phenylethyl)hydrazinylidene]methyl}phenol Copper (II) chloride, (PHPCu) complexes were prepared by reacting (1 mmol, 0.170 g) of copper chloride, CuCl₂·2H₂O, and (1 mmol, 0.481 g) of ligands (HMP and PHP) with 50 mL dioxane and reflux for 2 h to yield dark green powders with the yields of 95% and 98%.

RESULTS AND DISCUSSION:

The present investigation focused on the synthesis of transition metal complexes V(IV), Co(II), and Cu(II) utilizing the newly created ligands HMP and PHP. Schemes 1 and 2 depict the ligand manufacturing methods, whereas Table 1 summarizes the physical parameters of the ligands (HMP and PHP) and their metal complexes.

FTIR Spectra of the HMP PHP and their Metal complexes:

The IR data of the ligands (HMP and PHP) and metal complexes (HMPV, HMPCo, HMPCu, PHPV, PHPCo, and PHPCu) are presented in Table 2. The stretching vibration bands at 3450 cm⁻¹ and 3442 cm^-1are caused by the H-N groups of the ligands. The stretching bands due to the aromatic C-H were observed at 3453 and 2954 cm⁻¹for HMP and PHP respectively, while those for the aliphatic stretching were observed at 2922 and 2926 cm^-1for HMP and PHP respectively. The stretching bands at 1691 and 1693 cm−1 indicate azomethine C=N of HMP and PHP respectively. The stretching vibrations of the aromatic C=C were responsible for the 1581 and 1585 cm⁻¹ bands for HMP and PHP respectively, whereas the bending vibrations of the C-N group in the HMP and PHP caused the 1303 and 1306 cm⁻¹ band. For the metal complexes, the stretching vibrations of the O-H group were observed between 3400 and 3446 cm⁻¹, while those of the N-H group were found between 3261 and 3358 cm⁻¹. The stretching vibration band of the Ar C-H group was observed at 3053-3060 cm⁻¹, while those of the aliphatic C-H groups were responsible for the peaks at 2902-2926 cm⁻¹. The stretching vibration within the region of 736 and 734823 cm⁻¹ were attributed to the C-Cl groups of the ligands (HMP and PHP) respectively. As for the bonding of the ligands with transition metals, the bands showed a stretching vibration (which were absent in the spectra of the ligands) in the region of 522–561 cm⁻¹.^14,15 However, no broad band of stretching vibration of the O-H group was observed for the ligands HMP and PHP, indicating the formation of complexes.

Table 1: Physical properties of the new complexes

Compound	Molecular formula	M.wt (g/mol)	Color	Yield (%)
HMP	C₁₄H₁₄N₂O₂	242.27	Pale yellow	95
PHP	C₁₅H₁₆N₂O	240.3	Brownish yellow	97
HMPV	C₂₈H₃₆Cl₂N₄O₈V	678.45	Brown	90
PHPV	C₃₀H₃₆Cl₂N₄O₅V	654.48	Brown	92
HMPCo	C₂₈H₃₆Cl₂CoN₄O₈	686.45	Brown	98
PHPCo	C₃₀H₄₀Cl₂CoN₄O₆	682.5	Brown	96
HMPCu	C₂₈H₃₂Cl₂CuN₄O₆	655.03	Dark green	95
PHPCu	C₃₀H₃₆Cl₂CuN₄O₄	651.08	Dark green	98

Table 2: IR spectra data of the complexes

Complex	O-H	N-H	Ar-H	C-H	Stretching		C-N	C-Cl	Other
Complex	O-H	N-H	Ar-H	C-H	C=N	C=C	C-N	C-Cl	Other
HMP	-----	3450	3051	2922	1691	1581	1303	736	-----
PHP	-----	3442	3053	2926	1693	1585	1306	734	-----
HMPCu	3446	3358	3053	2926	1620	1558	1375	823	N-Cu 561
HMPV	3421	3344	3051	2921	1614	1554	1333	761	N-V 522
HMPCo	3400	3261	3060	2902	1656	1566	1377	750	N-Co 550
PHPCu	3446	3358	3053	2926	1620	1558	1375	823	N-Cu 558
PHPV	3421	3344	3051	2921	1614	1554	1333	761	N-V 545
PHPCo	3400	3261	3060	2902	1656	1566	1377	750	N-Co 572

Table 3. The 1H-NMR data of the ligand HMP and PHP

Compound

Structure

Chemical shift (ppm)

¹HNM

¹³CNMR

HMP

1. 7.04-7.27 (2H, d, Ar-H)

2. 7.38 (2H, t, Ar-H)

3. 7.20 (1H, t, Ar-H)

4. 6.37 (1H, s, C-H)

5. 6.90 (1H, s, O-H)

6. 7.78 (1H, s, N-H)

7. 6.26, 1H, s, C=N-H)

8. 6.90 (1H, s, O-H)

9. 7.38 (1H, d, Ar-H)

10. 7.45 (1H, t, Ar-H)

11. 7.47 (1H, t, Ar-H)

12. 7.38 (1H, d, Ar-H)

156.6 (1C,s C=N (L))

143.2 (1C,s C=N (M))

115.9-148.1 (3C, s, C=C (Conj. Alk.) (L))

71.7-139.5 (3C, s, C=C (Conj. Ar.) (M))

128.3-128.5 (3C, 128.4 s, C=C (Ar.) (L))

124.5-147.9 3C, 128.4 s, C=C (Ar.) (M))

125.9 (1C, s, C-M (M))

PHP

1. 7.04-7.27 (2H, d, Ar-H)

2. 7.38 (2H, d, Ar-H)

3. 7.20 (1H, t, Ar-H)

4. 7.02-7.16 (3H, s, CH₃)

5. 6.90 (1H, s, N-H)

6. 7.78 (1H, s, C=N-H)

7. 6.26, 1H, s, O-H)

8. 6.90 (1H, d, Ar-H)

9. 7.38 (1H, t, Ar-H)

10. 7.45 (1H, t, Ar-H)

11. 7.47 (1H, d, Ar-H)

12. 6.37 (1H, s, C-H)

156.6 (1C,s C=N (L))

143.2 (1C,s C=N (M))

115.9-148.1 (3C, s, C=C (Conj. Alk.) (L))

71.7-139.5 (3C, s, C=C (Conj. Alk.) (M))

128.3-128.5 (3C, 128.4 s, C=C (Ar.) (L))

124.5-147.9 3C, 128.4 s, C=C (Ar.) (M))

125.9 (1C, s, C-M (M))

L = Ligand, M= Metal complex

Bands associated to the C=N group were found at 1614-1656 cm⁻¹. The IR spectrum of all complexes revealed C=C stretching vibrations at 1554-1566 cm⁻¹, while C-N stretching vibrations were seen at 1333-1377 cm⁻¹.The C-Cl group was found to cause stretching vibrations between 750-823 cm⁻¹

1H-NMR and 13C-NMR Spectrum of HMP and PHP

The synthesized ligand's 1H-NMR spectra were acquired on a Bruker Avance 500 MHz spectrometer to confirm the hypothesized structure of QH in DMSO-d6, using tetramethylsilane (TMS) as an internal standard. The peaks at 2.5 and 3.3 ppm were identified as DMSO and water solutions, respectively ¹⁶. Table 3 presents the new compound's 1HNMR and ¹³C-NMR data.

Magnetic Susceptibility

Magnetic susceptibility is one way for studying the behavior of single electrons in complexes. When a central atom has single electrons, it exhibits paramagnetic qualities, while double electrons exhibit diamagnetic properties. This approach is effective for analyzing complex geometry, form, hybridization, and oxidation number ^{17, 18}. Complexes' magnetic characteristics result from orbital and perchance motion. Equation (1) defines the theoretical magnetic moment of metal ions in their first transition series.

(1)

Paramagnetic materials typically have both diamagnetic groups and paramagnetic cores. To minimize errors caused by magnetic influences, the magnetic susceptibility measurements must be corrected using Pascal's constants to determine the correction factor (D) ¹⁹. In this study, we used Faraday's approach for forbidden complexes and estimated magnetic moment values using the equations:

X_A = X_m –(-D) (2)

X_m= X_g x M

X_g represents weight susceptibility. M refers to the complex's molecular weight, while X_m represents its molar susceptibility. X_A: atom's susceptibility. D represents diamagnetic correction. μ_eff represents effective magnetic momentum. T represents absolute temperature. X_g is obtained from the device through practical measurements of the solid model.

The magnetic moment of HMPV and PHPV were 4.09 and 4.06 M.B (Table 4), demonstrating its paramagnetic nature due to three single electrons in the outer shell. Sp³d² hybridization resulted in an octahedral shape ²⁰. The HMPCo and PHPCo complexes were paramagnetic due to a single electron in their outer shells. The magnetic moment of the HMPCo and PHPCo indicated a square planer due to dsp² hybridization, while that of HMPCu and PHPCu revealed a square pyramidal shape due to dsp³ hybridization ^{21, 22}.

Table 4: Magnetic properties of the prepared complexes

Complex	*Xg 10−4**	XM	XA	D x 10⁻⁶	μ_eff B.M
HMPV	0.099	0.0067617	0.00692425	-162.65	4.09
HMPCo	0.018	0.001178	0.00130836	-136.56	1.78
HMPCu	0.021	0.0013755	0.00151206	-136.56	1.9
PHPV	0.098	0.0067628	0.00792425	-162.64	4.06
PHPCo	0.016	0.001166	0.00330836	-136.52	1.79
PHPCu	0.024	0.0013742	0.00651206	-136.52	1.91

Table 5: Molar conductivity of the complexes

Complex	Molar conductivity (mol⁻¹.cm².Ω⁻¹)
HMPV	140.8
HMCo	93.38
HMCu	132.6
PHPV	139.8
PHPCo	97.38
PHPCu	135.6

Molar Conductivity

Molar conductivity is widely used in coordination chemistry to determine the ionic formula of compounds in solid-state solutions ^23,
24. The more ions released by the complex in the solution, the higher its molar conductivity. Complexes having poor molar conductivity due to problematic ionization can be overlooked. The conductivity can be determined using the relationship below.

(3)

_m represents molar conductivity, while ∞ indicates electrical conductivity at the final dilution.

(4)

The readings in Table 5 indicated that the solutions were electrolytes.

The Electrospray Ionization (ESI)

The soft ionization mass spectrum can reveal the molecular structure of molecules by detecting the presence of molecular ions, which correspond to the compound's molecular weight. Table 6 and 7 show the spectrum data. The protonation ion [M⁺H]⁺ can be used to determine a compound's molecular weight. The ESI mass spectra of complexes revealed a molecular ion peak at [M+1]+. Mass spectra confirmed the hypothesized chemical structure of the complexes.

Thermal Analysis

Thermal analysis (TG and DTG) was used to assess the thermal stability of the complexes and determine if water molecules were inside or outside the central metal ion's coordination sphere. To conduct TG analysis, the complexes were heated to 700 °C in nitrogen at a rate of 10 °C per minute. The mass losses calculated using TG curves were nearly identical to the calculated values. The proposed structures are supported by diverse degradation pathways ^{25, 26}. Table 8 shows the thermal breakdown data for the complexes, indicating that the remaining components were more stable ²⁷.

Table 6: The ESI of the HMP complexes

	Complex
	HMPV	HMPCo	HMPCu
Structure
M.wt	678	654	686
[M+H]⁺	679	655	687

Table 7: The ESI of the HMP complexes

	Complex
	PHPV	PHPCo	PHPCu
Structure
M.wt	682	655	651
[M+H]⁺	683	656	652

Table 8: Thermogravimetric analysis of the prepared complexes

Complex

Decomp. Temp. (⁰C)

Char content at 600 ⁰C

Mass loss %

(theoretical)

Assignment

T_i

T_max

T_final

HMPV

150

320

133

300

420

150

320

600

38.35%

10.5 (10.7)

10.5 (10.6)

40.35

H₂O crystallization

H₂O coordination

Survival part of the ligand

HMPCo

100

170

270

140

220

300

170

270

600

55.84%

5.5 (5.51)

11 (10.4)

25.15

H₂O crystallization

4H₂O coordination

Survival part of the ligand

HMPCu

150

350

130

305

470

150

350

600

75.43%

5.49 (5.51)

10.98 (11.8)

7.26

H₂O crystallization

H₂O coordination

Survival part of the ligand

PHPV

150

350

135

320

400

140

280

420

45.24%

10.3 (10.7)

10.4 (10.6)

41.35

H₂O crystallization

H₂O coordination

Survival part of the ligand

PHPCo

100

150

250

120

250

350

170

250

400

82.35%

5.4 (5.51)

11.2 (10.4)

26.15

H₂O crystallization

4H₂O coordination

Survival part of the ligand

PHPCu

150

320

150

300

420

120

320

600

86.12%

5.39 (5.51)

11.35 (11.8)

8.26

H₂O crystallization

H₂O coordination

Survival part of the ligand

For the vanadium complexes, the first stage ranges from 90-150 °C and 150 – 140 ⁰C (DTGmax and 150 ⁰C and 140 °C), resulting in a practical losses of 10.5% and 10.3% and a theoretical loss of 10.7% due to crystallization water molecule (H₂O). The second stage at 150-320 °C and 150 – 280 ⁰C (DTG_max 320 °C and 280 ⁰C) resulted in the loss of two molecules of coordinated water (2H₂O), whereas the third stage at 320-600 °C and 350 – 420 ⁰C (DTGmax 600 and420 °C) resulted in the loss of portions of the ligand (40.35% and 41.35% loss and 38.35% and 45.24% residual survival) exceeding the theoretical ratio of 10.7% for vanadium oxide (VO). The compound is thermally stable and exhibits strong ligand-metal bonding.

The thermal study of the HMPCo and PHPCo show multiple stages of loss. The first stage ranges from 100-170 °C (DTGmax 140 °C), resulting in a practical losses of 5.5% and 5.4% and a theoretical loss of 5.51% due to crystallization water molecule (H₂O). The second stage at 170-270 °C (DTGmax 220 °C) resulted in the loss of four molecules of coordinated water (4H₂O), whereas the third stage at 270-600 °C (DTGmax 300 °C) resulted in the loss of portions of the ligand (25.15% and 26.15% loss and 55.84% and 83.35% residual). This proportion exceeds the theoretical value of 10.4% for cobalt oxide (CoO), indicating the existence of organic ligands coupled to the metal.

The thermal data of the HMPCu and PHPCu complex at 100-170 °C (DTGmax 130 °C) show a loss of one molecule of crystallization water (H₂O), with practical losses ratio of 5.51% and 5.39 and a theoretical loss ratio of 5.51%. At the second stage of 170-270 °C (DTGmax 305 °C), the practical loss ratios were 10.98% and 11.35, while the theoretical ratio was 11.8%, indicating the loss of one molecule of coordinated water (2H₂O). The third stage was visible in the spectrum (TG, DTG) at 350-600 °C (DTGmax 470 °C) due to ligand loss of 7.26% and 8.26 with a residual ratios of 75.43% and 86.12% for HMPCu and PHPCu respectively. This indicates that parts of the ligand survived the process, exceeding the percentage of Copper oxide (CUO). This is due to the complex's high temperature stability and strong ligand-metal interactions.

Overall, the investigated results show that the proposed complexes' forms are accurate ¹⁹. The mass spectrum and thermal examination of the complexes revealed their molecular weights and the presence of water of coordination, consistent with their compositions. Molar conductivity indicated that the complexes were ionic, with chlorine ions present outside the coordination sphere. The magnetic susceptibility analysis revealed the hybridization and geometrical forms of molecules based on the number of single electrons per metal ion.

Calculation of the Thermodynamic Functions of the Prepared Complexes:

The thermodynamic functions of the compounds in this investigation were estimated at temperatures ranging from 150 to 600 °C (see Table 9). Data show a progressive increase in stability constants at higher temperatures. The study's stability constants increased with temperature, allowing for a thermodynamic analysis of the interaction. The Coats-Redfern equation, represented by Eq. (5) ²⁸, yielded changes in enthalpy (ΔH), free energy (ΔG), and entropy (ΔS) deduced from equation 6.

(5)

In this equation, W_f represents weight loss at the end of the stage, W_t represents weight loss at a specific temperature (t), E represents activation energy, A is constant, θ is constant, R is the gas constant (8.314^M−1.J⁻¹.K), and T represents absolute temperature. From the liner plot between vs. , the slope and intercept can be used to determine the kinetic parameters. Where g(a) represents .

(6)

Calculating the thermodynamic functions using the given equation gives the results that follow. Negative ΔS values indicate that the processes occurred at a slow rate and that the activated complex was more ordered than the reactants. Furthermore, all complexes had positive activation ΔH values, indicating an endothermic reaction. Table 9 shows that all ΔG values were positive, indicating non-spontaneous steps.

Complex

Stage

A (S^-1)

E (kJ.mol^-1)

△H (kJ.mol^-1)

△S (kJ.mol^-1.K^-1)

△G (kJ.mol^-1)

HMPV

1.01 x 10⁶

1.00 x 10¹¹

1.80 x 10¹

1.90 x 10²

13.16

191.80

-0.14

-0.04

9.12 x 10¹

3.23 x 10²

HMPCo

2.19 x 10⁴

5.20 x 10¹³

6.25 x 10¹

1.52 x 10¹²

59.12

147.20

-0.16

0.01

1.25 x 10⁵

1.54 x 10²

HMPCu

III

2.18 x 10⁵

7.21 x 10²²

8.51 x 10⁹

5.97 x 10¹

1.20 x 10²

1.19 x 10²

56.79

196.38

114.45

-0.14

0.19

-0.06

1.06 x 10²

-1.18 x 10¹

1.44 x 10²

PHPV

1.03 x 10⁶

1.14 x 10¹¹

1.82 x 10¹

1.94 x 10²

13.14

191.81

-0.14

-0.05

9.13 x 10¹

3.22 x 10²

PHVCo

2.15 x 10⁴

5.32 x 10¹³

6.21 x 10¹

1.73 x 10¹²

59.13

147.21

-0.15

0.02

1.26 x 10⁵

1.53 x 10²

PHPCu

III

2.12 x 10⁵

6.91 x 10²²

8.41 x 10⁹

5.97 x 10¹

1.13 x 10²

1.29 x 10²

56.76

196.32

114.46

-0.13

0.18

-0.05

1.05 x 10²

-1.17 x 10¹

1.43 x 10²

CONCLUSION:

We successfully synthesized novel V(IV), Co(II), and Cu(II) complexes using quinoline-thiocarbohydrizide ligands with diverse steric and electrical characteristics in high yields. The novel compounds have been thoroughly studied using FTIR, 1H-NMR, 13C-NMR, ESI-MS, TGA, molar conductance, magnetic susceptibility, and thermodynamic function. The examined compounds were found to be more stable at 700°C. This study suggests that the produced hydrazone ligand and its transition metal complexes could be effective in biological studies.

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Received on 13.09.2024 Revised on 26.10.2024

Accepted on 25.11.2024 Published on 11.12.2024

Available online on December 31, 2024

International Journal of Technology. 2024; 14(2):69-77.

DOI: 10.52711/2231-3915.2024.00010

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